Details of the Researcher

PHOTO

Takayuki Doi
Section
Graduate School of Pharmaceutical Sciences
Job title
Professor
Degree

  • 工学博士（東京工業大学）

  • 工学修士（東京工業大学）

e-Rad No.
90212076

Research History 6

  • 2018/04 - Present
    Tohoku Univ. Graduate School of Life Sciences

  • 2008/04 - Present
    Tohoku Univ, Graduate School of Pharmaceutical Sciences　Heterocyclic Chemistry　Professor

  • 2007/04 - 2008/03
    Department of Applied Chemistry, Tokyo Institute of Technology　associate professor

  • 2001/02 - 2007/03
    Department of Applied Chemistry, Tokyo Institute of Technology　associate professor

  • 1993/10 - 2001/01
    Faculty of Engineering, Tokyo Institute of Technology　assistant professor

  • 1991/04 - 1993/09
    Columbia University, Department of Chemistry　Postdoctoral Research Scientist

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Education 2

  • Tokyo Institute of Technology　Graduate School, Division of Science and Engineering　Department of Chemical Engineering

    1986/04 - 1991/03

  • Tokyo Institute of Technology　Faculty of Engineering　Department of Chemical Engineering

    1982/04 - 1986/03

Committee Memberships 20

  • ACS Omega　Editorial Advisory Board

    2017/01 - Present

  • Bulletin of Chemical Society Japan　編集委員

    2011/01 - Present

  • 日本ペプチド学会　評議員

    2018/04 - 2022/03

  • 日本薬学会　代議員

    2017/03 - 2022/03

  • Combinatorial Chemistry & High Throughput Screening　Editorial Advisory Board Members

    2008 - 2020/09

  • 10th International Peptide Symposium in Kyoto　プログラム委員

    2016/07 - 2018/12

  • 第１０回国際ペプチドシンポジウム　プログラム委員

    2016/07 - 2018/12

  • 有機合成化学協会　東北支部長 理事

    2016/01 - 2017/12

  • 7th CCS-CSJ Young Chemists Forum 2017　co-chair

    2016/11 - 2017/03

  • 日本化学会年会・第７回日中フォーラム　実行副委員長

    2016/11 - 2017/03

  • 日本薬学会第１３７年会　化学系薬学プログラム委員長

    2016/08 - 2017/03

  • 第５８回天然有機化合物討論会　実行委員会副委員長

    2016/02 - 2016/09

  • 有機合成化学協会　代議員

    2014/01 - 2015/12

  • 日本薬学会　東北支部代議員

    2012/04 - 2015/02

  • Chemical Society of Japan　春季年会プログラム編集部門長

    2007/08 - 2009/03

  • 日本化学会　春季年会プログラム編集部門長

    2007/08 - 2009/03

  • Japan Combinatorial Chemistry Focusing Group　organizing committee

    1998/01 - 2009/03

  • コンビケム研究会　幹事

    1998/01 - 2009/03

  • The Society of Synthetic Organic Chemistry, Japan　事業委員

    2006/02 - 2008/12

  • 有機合成化学協会　事業委員

    2006/02 - 2008/12

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Professional Memberships 7

  • The Chem-Bio Information Society

    2020/05 - Present

  • 日本ケミカルバイオロジー学会

  • 近畿化学協会

  • 日本ペプチド学会

  • 有機合成化学協会

  • 日本化学会

  • 日本薬学会

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Research Interests 5

  • heteroaromatic compound

  • cyclic peptide

  • combinatorial synthesis

  • natural product synthesis

  • oraganic synthesis

Research Areas 3

  • Nanotechnology/Materials / Synthetic organic chemistry /

  • Nanotechnology/Materials / Molecular biochemistry /

  • Life sciences / Pharmaceuticals - chemistry and drug development /

Awards 5

  1. 住木・梅澤記念賞

    2021/11　公益財団法人 日本感染症医薬品協会　創薬を指向した生物活性環状ペプチド天然物の革新的合成法とその応用に関する研究

  2. Shionogi Award

    2020/02　The Society of Synthetic Chemistry Japan

  3. 長瀬研究振興賞

    2015/04/23　公益財団法人 長瀬科学技術振興財団　タンパク質間相互作用阻害化合物の創製

  4. 日本薬学会学術振興賞

    2013/03　日本薬学会

  5. 有機合成化学奨励賞

    2000/02　有機合成化学協会

Papers 175

  1. Photocatalyzed Oxidative Decarboxylation Forming Aminovinylcysteine Containing Peptides

    Masaya Kumashiro, Kosuke Ohsawa, Takayuki Doi

    Catalysts　12　(12)　1615-1615　2022/12/09

    Publisher: MDPI AG

    DOI： 10.3390/catal12121615 　

    eISSN： 2073-4344

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    The formation of (2S,3S)-S-[(Z)-aminovinyl]-3-methyl-D-cysteine (AviMeCys) substructures was developed based on the photocatalyzed-oxidative decarboxylation of lanthionine-bearing peptides. The decarboxylative selenoetherification of the N-hydroxyphthalimide ester, generated in situ, proceeded under mild conditions at −40 °C in the presence of 1 mol% of eosin Y-Na2 as a photocatalyst and the Hantzsch ester. The following β-elimination of the corresponding N,Se-acetal was operated in a one-pot operation, led to AviMeCys substructures found in natural products in moderate to good yields. The sulfide-bridged motif, and also the carbamate-type protecting groups, such as Cbz, Teoc, Boc and Fmoc groups, were tolerant under the reaction conditions.

  2. Synthetic studies for destruxins and biological evaluation for osteoclast-like multinucleated cells: a review. International-journal

    Masahito Yoshida, Hiroshi Nakagawa, Takayuki Doi

    The Journal of antibiotics　75　(8)　420-431　2022/08

    DOI： 10.1038/s41429-022-00540-8 　

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    Synthesis of various destruxin analogs was accomplished using Shiina's macrolactonization as a key reaction. Combinatorial synthesis of cyclization precursors using solid-phase peptide synthesis and macrolactonization in solution were successful. In the synthesis of destruxin E and its analogs, the hydroxyacid-proline (HA1-Pro2) dipeptide with an acetonide-protected diol moiety was synthesized in an asymmetric manner, and the protected diol was converted to an epoxide after macrocyclization. Destruxin E was synthesized on a gram scale using solution-phase synthesis. The structure-activity relationships of destruxins were elucidated through biological evaluation of synthetic destruxins A, B, and E and their analogs for morphological changes in osteoclast-like multinucleated cells.

  3. Total Synthesis and Structural Determination of Cyclodepsipeptide Decatransin

    Kosuke Ohsawa, Sakiko Fukaya, Takayuki Doi

    Organic Letters　2022/07/22

    Publisher: American Chemical Society (ACS)

    DOI： 10.1021/acs.orglett.2c02085 　

    ISSN： 1523-7060

    eISSN： 1523-7052

  4. A Phenylfurocoumarin Derivative Reverses ABCG2-Mediated Multidrug Resistance In Vitro and In Vivo

    Shoji Kokubo, Shinobu Ohnuma, Megumi Murakami, Haruhisa Kikuchi, Shota Funayama, Hideyuki Suzuki, Taiki Kajiwara, Akihiro Yamamura, Hideaki Karasawa, Norihiko Sugisawa, Kosuke Ohsawa, Kuniyuki Kano, Junken Aoki, Takayuki Doi, Takeshi Naitoh, Suresh V. Ambudkar, Michiaki Unno

    International Journal of Molecular Sciences　22　(22)　12502-12502　2021/11/19

    Publisher: MDPI AG

    DOI： 10.3390/ijms222212502 　

    eISSN： 1422-0067

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    The ATP-binding cassette subfamily G member 2 (ABCG2) transporter is involved in the development of multidrug resistance in cancer patients. Many inhibitors of ABCG2 have been reported to enhance the chemosensitivity of cancer cells. However, none of these inhibitors are being used clinically. The aim of this study was to identify novel ABCG2 inhibitors by high-throughput screening of a chemical library. Among the 5812 compounds in the library, 23 compounds were selected in the first screening, using a fluorescent plate reader-based pheophorbide a (PhA) efflux assay. Thereafter, to validate these compounds, a flow cytometry-based PhA efflux assay was performed and 16 compounds were identified as potential inhibitors. A cytotoxic assay was then performed to assess the effect these 16 compounds had on ABCG2-mediated chemosensitivity. We found that the phenylfurocoumarin derivative (R)-9-(3,4-dimethoxyphenyl)-4-((3,3-dimethyloxiran-2-yl)methoxy)-7H-furo [3,2-g]chromen-7-one (PFC) significantly decreased the IC50 of SN-38 in HCT-116/BCRP colon cancer cells. In addition, PFC stimulated ABCG2-mediated ATP hydrolysis, suggesting that this compound interacts with the substrate-binding site of ABCG2. Furthermore, PFC reversed the resistance to irinotecan without causing toxicity in the ABCG2-overexpressing HCT-116/BCRP cell xenograft mouse model. In conclusion, PFC is a novel inhibitor of ABCG2 and has promise as a therapeutic to overcome ABCG2-mediated MDR, to improve the efficiency of cancer chemotherapy.

  5. JBIR-155, a Specific Class D β-Lactamase Inhibitor of Microbial Origin. International-journal

    Takehiro Nishimura, Teppei Kawahara, Noritaka Kagaya, Yusuke Ogura, Hirosato Takikawa, Hikaru Suenaga, Masaatsu Adachi, Takatsugu Hirokawa, Takayuki Doi, Kazuo Shin-Ya

    Organic letters　23　(11)　4415-4419　2021/06/04

    DOI： 10.1021/acs.orglett.1c01352 　

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    We discovered JBIR-155 as a novel specific class D β-lactamase inhibitor from Streptomyces polymachus SoB100815Hv02. JBIR-155 consists of a 6-oxabicyclo[3.2.0]heptan-7-one skeleton and a long unsaturated alkyl chain moiety of which absolute configuration was determined by spectroscopic data, modified Mosher's method, and analyses of the relative configuration of chemically modified derivative. JBIR-155 specifically exhibited inhibitory activity against the class D β-lactamase, with an IC50 value of 0.36 μM.

  6. Stereoselective Synthesis of 1-Aminocyclopropanecarboxylic Acid Carnosadines via Inter-intramolecular Double Alkylation with Optically Active 2-Methylaziridine Derivatives. International-journal

    Kosuke Ohsawa, Junya Kubota, Shota Ochiai, Takayuki Doi

    The Journal of organic chemistry　86　(10)　7304-7313　2021/05/21

    DOI： 10.1021/acs.joc.1c00680 　

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    The stereoselective and short-step synthesis of N-protected allo-carnosadine, ent-carnosadine, and carnosadine lactam was accomplished from a common cyclopropane intermediate. The inter-intramolecular double alkylation of diethyl malonate with an optically active 2-methylaziridine derivative gave the key cyclopropane in excellent yield and optical purity. The following monohydrolysis of the diester moiety using different reaction conditions provided both diastereomers of monoacids, which were converted to three carnosadine derivatives in 5-6 steps from the common diester.

  7. Gold-Catalyzed Amide/Carbamate-Linked N,O-Acetal Formation with Bulky Amides and Alcohols. International-journal

    Kosuke Ohsawa, Shota Ochiai, Junya Kubota, Takayuki Doi

    The Journal of organic chemistry　86　(1)　1281-1291　2021/01/01

    DOI： 10.1021/acs.joc.0c02640 　

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    A gold-catalyzed N,O-acetal formation was established to construct an amide/carbamate-linked N,O-acetal substructure with bulky alcohols. The acyliminium cation species generated from o-alkynylbenzoic acid ester in the presence of a gold catalyst is highly reactive and underwent nucleophilic attack of various bulky alcohols and phenols at room temperature under neutral conditions, leading to the corresponding N,O-acetals in yields of 34-89% with good functional group tolerance.

  8. The Anti-atherogenic Activity of Beauveriolide Derivative BVD327, a Sterol O-Acyltransferase 2-Selective Inhibitor, in Apolipoprotein E Knockout Mice Peer-reviewed

    Taichi Ohshiro, Satoshi Imuta, Ichiro Hijikuro, Hiroaki Yagyu, Takashi Takahashi, Takayuki Doi, Shun Ishibashi, Hiroshi Tomoda

    Biological and Pharmaceutical Bulletin　43　(6)　951-958　2020/06/01

    Publisher: Pharmaceutical Society of Japan

    DOI： 10.1248/bpb.b19-00913 　

    ISSN： 0918-6158

    eISSN： 1347-5215

  9. C-Methylation of S-adenosyl-L-Methionine Occurs Prior to Cyclopropanation in the Biosynthesis of 1-Amino-2-Methylcyclopropanecarboxylic Acid (Norcoronamic Acid) in a Bacterium. International-journal Peer-reviewed

    Chitose Maruyama, Yukiko Chinone, Shusuke Sato, Fumitaka Kudo, Kosuke Ohsawa, Junya Kubota, Junko Hashimoto, Ikuko Kozone, Takayuki Doi, Kazuo Shin-Ya, Tadashi Eguchi, Yoshimitsu Hamano

    Biomolecules　10　(5)　775　2020/05/16

    DOI： 10.3390/biom10050775 　

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    Many pharmacologically important peptides are bacterial or fungal in origin and contain nonproteinogenic amino acid (NPA) building blocks. Recently, it was reported that, in bacteria, a cyclopropane-containing NPA 1-aminocyclopropanecarboxylic acid (ACC) is produced from the L-methionine moiety of S-adenosyl-L-methionine (SAM) by non-canonical ACC-forming enzymes. On the other hand, it has been suggested that a monomethylated ACC analogue, 2-methyl-ACC (MeACC), is derived from L-valine. Therefore, we have investigated the MeACC biosynthesis by identifying a gene cluster containing bacterial MeACC synthase genes. In this gene cluster, we identified two genes, orf29 and orf30, which encode a cobalamin (B12)-dependent radical SAM methyltransferase and a bacterial ACC synthase, respectively, and were found to be involved in the MeACC biosynthesis. In vitro analysis using their recombinant enzymes (rOrf29 and rOrf30) further revealed that the ACC structure of MeACC was derived from the L-methionine moiety of SAM, rather than L-valine. In addition, rOrf29 was found to catalyze the C-methylation of the L-methionine moiety of SAM. The resulting methylated derivative of SAM was then converted into MeACC by rOrf30. Thus, we demonstrate that C-methylation of SAM occurs prior to cyclopropanation in the biosynthesis of a bacterial MeACC (norcoronamic acid).

  10. Stereoselective Synthesis of Protected L-allo-Enduracididine and L-Enduracididine via Asymmetric Nitroaldol Reaction Peer-reviewed

    Kosuke Ohsawa, Hongbin Zhao, Takuya Tokunaga, Carys Thomas, A. Ganesan, Yuichi Masuda, Takayuki Doi

    SYNTHESIS-STUTTGART　52　(6)　942-948　2020/03

    DOI： 10.1055/s-0039-1691522 　

    ISSN： 0039-7881

    eISSN： 1437-210X

  11. Electrochemical Detection of Kallikrein Using a p-Methoxyaniline-conjugated Tripeptide towards Simple Diagnosis of Primary Aldosteronism Peer-reviewed

    Kousuke Ohyama, Sun Sixiang, Kumi Y. Inoue, Tomokazu Matsue, Takayuki Doi

    Chemistry Letters　49　(1)　57-59　2020/01/05

    DOI： 10.1246/cl.190729 　

    ISSN： 0366-7022

    eISSN： 1348-0715

  12. Palladium(0)-Catalyzed [4+2] Annulation of Salicylaldehydes and Propargyl Carbonates to Produce 3,4-Dihydro-2-Methylene-2H-1-Benzopyran-4-Ols Peer-reviewed

    Ayumu Kawase, Hirotaka Omura, Takayuki Doi, Hirokazu Tsukamoto

    Chemistry Letters　48　(11)　1402-1405　2019/11

    DOI： 10.1246/cl.190642 　

  13. Structure－Activity Relationship Study on Col-003, a Protein－Protein Interaction Inhibitor between Collagen and Hsp47 Peer-reviewed

    Masahito Yoshida, Masazumi Saito, Shinya Ito, Koji Ogawa, Naoki Goshima, Kazuhiro Nagata, Takayuki Doi

    Chemical & Pharmaceutical Bulletin　2019/10

    DOI： 10.1248/cpb.c19-00634 　

  14. Key Factors for High Diastereo- and Enantioselectivity of Umpolung Cyclizations of Aldehyde-Containing Allylpalladium Intermediates Peer-reviewed

    Hirokazu Tsukamoto, Ayumu Kawase, Hirotaka Omura, Takayuki Doi

    Bulletin of the Chemical Society of Japan　92　(10)　1743-1753　2019/10

    DOI： 10.1246/bcsj.20190167 　

  15. A BRET-based assay reveals collagen-Hsp47 interaction dynamics in the endoplasmic reticulum and small-molecule inhibition of this interaction. Peer-reviewed

    Ito S, Saito M, Yoshida M, Takeuchi K, Doi T, Nagata K

    The Journal of biological chemistry　2019/09

    DOI： 10.1074/jbc.RA119.010567 　

    ISSN： 0021-9258

  16. SYNTHESIS OF A BIPHENYLALANINE ANALOGUE OF APRATOXIN A DISPLAYING SUBSTANTIALLY ENHANCED CYTOTOXICITY Invited Peer-reviewed

    Yuichi Onda, Kazuki Fukushi, Kosuke Ohsawa, Masahito Yoshida, Yuichi Masuda, Takayuki Doi

    HETEROCYCLES　101　(2)　679-691　2019/09

    DOI： 10.3987/COM-19-S(F)35 　

    ISSN： 0385-5414

    eISSN： 1881-0942

  17. Palladium(0)-Lithium Iodide-Cocatalyzed Asymmetric Hydroalkylation of Conjugated Enynes with Pronucleophiles Leading to 1,3-Disubstituted Allenes Peer-reviewed

    Hirokazu Tsukamoto, Tatsuya Konno, Kazuya Ito, Takayuki Doi

    Organic Letters　21　(17)　6811-6814　2019/08

    DOI： 10.1021/acs.orglett.9b02439 　

  18. Identification of Celastramycin as a Novel Therapeutic Agent for Pulmonary Arterial Hypertension. International-journal Peer-reviewed

    Ryo Kurosawa, Kimio Satoh, Nobuhiro Kikuchi, Haruhisa Kikuchi, Daisuke Saigusa, Md Elias Al-Mamun, Mohammad A H Siddique, Junichi Omura, Taijyu Satoh, Shinichiro Sunamura, Masamichi Nogi, Kazuhiko Numano, Satoshi Miyata, Akira Uruno, Kuniyuki Kano, Yotaro Matsumoto, Takayuki Doi, Junken Aoki, Yoshiteru Oshima, Masayuki Yamamoto, Hiroaki Shimokawa

    Circulation research　125　(3)　309-327　2019/07/19

    DOI： 10.1161/CIRCRESAHA.119.315229 　

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    RATIONALE: Pulmonary arterial hypertension (PAH) is characterized by enhanced proliferation of pulmonary artery smooth muscle cells (PASMCs) accompanying increased production of inflammatory factors and adaptation of the mitochondrial metabolism to a hyperproliferative state. However, all the drugs in clinical use target pulmonary vascular dilatation, which may not be effective for patients with advanced PAH. OBJECTIVE: We aimed to discover a novel drug for PAH that inhibits PASMC proliferation. METHODS AND RESULTS: We screened 5562 compounds from original library using high-throughput screening system to discover compounds which inhibit proliferation of PASMCs from patients with PAH (PAH-PASMCs). We found that celastramycin, a benzoyl pyrrole-type compound originally found in a bacteria extract, inhibited the proliferation of PAH-PASMCs in a dose-dependent manner with relatively small effects on PASMCs from healthy donors. Then, we made 25 analogs of celastramycin and selected the lead compound, which significantly inhibited cell proliferation of PAH-PASMCs and reduced cytosolic reactive oxygen species levels. Mechanistic analysis demonstrated that celastramycin reduced the protein levels of HIF-1α (hypoxia-inducible factor 1α), which impairs aerobic metabolism, and κB (nuclear factor-κB), which induces proinflammatory signals, in PAH-PASMCs, leading to reduced secretion of inflammatory cytokine. Importantly, celastramycin treatment reduced reactive oxygen species levels in PAH-PASMCs with increased protein levels of Nrf2 (nuclear factor erythroid 2-related factor 2), a master regulator of cellular response against oxidative stress. Furthermore, celastramycin treatment improved mitochondrial energy metabolism with recovered mitochondrial network formation in PAH-PASMCs. Moreover, these celastramycin-mediated effects were regulated by ZFC3H1 (zinc finger C3H1 domain-containing protein), a binding partner of celastramycin. Finally, celastramycin treatment ameliorated pulmonary hypertension in 3 experimental animal models, accompanied by reduced inflammatory changes in the lungs. CONCLUSIONS: These results indicate that celastramycin ameliorates pulmonary hypertension, reducing excessive proliferation of PAH-PASMCs with less inflammation and reactive oxygen species levels, and recovered mitochondrial energy metabolism. Thus, celastramycin is a novel drug for PAH that targets antiproliferative effects on PAH-PASMCs.

  19. Palladium-Catalyzed Umpolung Type-II Cyclization of Allylic Carbonate-Aldehydes Leading to 3-Methylenecycloalkanol Derivatives Peer-reviewed

    Hirokazu Tsukamoto, Ayumu Kawase, Takayuki Doi

    Advanced Synthesis & Catalysis　361　(16)　3733-3738　2019/05

    DOI： 10.1002/adsc.201900450 　

  20. Total Synthesis and Structural Revision of Cyclotetrapeptide Asperterrestide A. International-journal Peer-reviewed

    Kosuke Ohsawa, Masato Sugai, Linnan Zhang, Yuichi Masuda, Masahito Yoshida, Takayuki Doi

    The Journal of organic chemistry　84　(11)　6765-6779　2019/05

    DOI： 10.1021/acs.joc.9b00526 　

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    The structural revision of cyclotetrapeptide asperterrestide A has been achieved based on total synthesis and molecular modeling. For these studies, (2 R,3 S)-MePhe(3-OH) and (2 S,3 S)-MePhe(3-OH) suitably protected for peptide synthesis were prepared via a stereoselective reduction of a ketone precursor derived from L- or d-serine, using L-selectride or DIBAL-H. The synthesis of the proposed structure of asperterrestide A (1a) was accomplished by solution-phase synthesis of a linear precursor followed by macrolactamization. The NMR spectra of our synthetic 1a were not identical to those reported for the natural compound. Molecular modeling studies suggested that the correct structure 1b was the one in which the stereochemistry at the α-positions of the Ala and MePhe(3-OH) residues is the opposite to that of the proposed structure. This was confirmed by the total synthesis of 1b and its subsequent structural characterization.

  21. Parallel Synthesis and Biological Evaluation of Destruxin E Analogs Modified with a Side Chain in the alfa-Hydroxycarboxylic Acid Moiety Peer-reviewed

    Masahito Yoshida, Kenta Adachi, Hayato Murase, Hiroshi Nakagawa, Takayuki Doi

    European Journal of Organic Chemistry　2019　1669-1676　2019/01

    DOI： 10.1002/ejoc.201801826 　

  22. First Total Synthesis of Palmarumycin C6 Based on Double Oxa-Michael Addition of 1,8-Dihydroxynaphthalene to 3-Bromo-1-indenone Invited Peer-reviewed

    Hirokazu Tsukamoto, Yumi Nomura, Takayuki Doi

    Heterocycles　99　(1)　549-565　2019/01

    DOI： 10.3987/COM-18-S(F)52 　

  23. Toward Structural Understanding of Ligand Recognition by Lysophosphatidic Acid Receptor Lpa6 Peer-reviewed

    Taniguchi Reiya, Inoue Asuka, Sayama Misa, Yamashita Keitaro, Hirata Kunio, Yoshida Masahito, Nakada-Nakura Yoshiko, Otani Yuko, Kato Hideaki, Nishizawa Tomohiro, Doi Takayuki, Ohwada Tomohiko, Ishitani Ryuichiro, Aoki Junken, Nureki Osamu

    PROTEIN SCIENCE　27　235-236　2018/11

    ISSN： 0961-8368

  24. Cyclodepsipeptide Natural Products Apratoxins A and C and Their Analogs Invited Peer-reviewed

    Takayuki Doi, Yuichi Masuda, Masahito Yoshida

    Journal of Synthetic Organic Chemistry, Japan　76　(11)　1170-1175　2018/11

    DOI： 10.5059/yukigoseikyokaishi.76.1170 　

    ISSN： 0037-9980

  25. Synthesis and biological evaluation of thielocin B1 analogues as protein-protein interaction inhibitors of PAC3 homodimer International-journal Peer-reviewed

    Kosuke Ohsawa, Masahito Yoshida, Miho Izumikawa, Motoki Takagi, Kazuo Shin-ya, Naoki Goshima, Takatsugu Hirokawa, Tohru Natsume, Takayuki Doi

    Bioorganic Medicinal Chemistry　26　(23-24)　6023-6034　2018/11

    DOI： 10.1016/j.bmc.2018.11.001 　

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    The synthesis and biological evaluation of thielocin B1 analogues have been demonstrated. Fourteen analogues modified in the central core and terminal carboxylic acid moiety were concisely synthesized by simple esterification or etherification reaction. The evaluation of synthetic analogues as inhibitors of proteasome assembling chaperone (PAC) complexes (the PAC3 homodimer and PAC1/PAC2) revealed that the natural product-like bending structure and terminal carboxylic acid groups were crucial for its biological activity. Moreover, SAR and in silico docking studies indicated that all methyl groups on the diphenyl ether moiety of thielocin B1 contribute to the potent and selective inhibition of the PAC3 homodimer via hydrophobic interactions.

  26. A novel potent ABCB1 modulator, phenethylisoquinoline alkaloid, reverses multidrug resistance in cancer cell International-journal Peer-reviewed

    Norihiko Sugisawa, Shinobu Ohnuma, Hirofumi Ueda, Megumi Murakami, Kyoko Sugiyama, Kosuke Ohsawa, Kuniyuki Kano, Hidetoshi Tokuyama, Takayuki Doi, Junken Aoki, Masaharu Ishida, Katsuyoshi Kudoh, Takeshi Naitoh, Suresh V. Ambudkar, Michiaki Unno

    Molecular Pharmaceutics　15　(9)　4021-4030　2018/07

    DOI： 10.1021/acs.molpharmaceut.8b00457 　

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    ATP-binding cassette (ABC) transporters, which are concerned with the efflux of anticancer drugs from cancer cells, have a pivotal role in multidrug resistance (MDR). In particular, ABCB1 is a well-known ABC transporter that develops MDR in many cancer cells. Some ABCB1 modulators can reverse ABCB1-mediated MDR; however, no modulators with clinical efficacy have been approved. The aim of this study was to identify novel ABCB1 modulators by using high-throughput screening. Of the 5861 compounds stored at Tohoku University, 13 compounds were selected after the primary screening via a fluorescent plate reader-based calcein acetoxymethylester (AM) efflux assay. These 13 compounds were validated in a flow cytometry-based calcein AM efflux assay. Two isoquinoline derivatives were identified as novel ABCB1 inhibitors, one of which was a phenethylisoquinoline alkaloid, (±)-7-benzyloxy-1-(3-benzyloxy-4-methoxyphenethyl)-1,2,3,4-tetrahydro-6-methoxy-2-methylisoquinoline oxalate. The compound, a phenethylisoquinoline alkaloid, was subsequently evaluated in the cytotoxicity assay and shown to significantly enhance the reversal of ABCB1-mediated MDR. In addition, the compound activated the ABCB1-mediated ATP hydrolysis and inhibited the photolabeling of ABCB1 with [125I]-iodoarylazidoprazosin. Furthermore, the compound also reversed the resistance to paclitaxel without increasing the toxicity in the ABCB1-overexpressing KB-V1 cell xenograft model. Overall, we concluded that the newly identified phenethylisoquinoline alkaloid reversed ABCB1-mediated MDR through direct interaction with the substrate-binding site of ABCB1. These findings may contribute to the development of more potent and less toxic ABCB1 modulators, which could overcome ABCB1-mediated MDR.

  27. Total Synthesis of Spiromamakone A and Structure Revision of Spiropreussione A Peer-reviewed

    Hirokazu Tsukamoto, Shogo Hanada, Yumi Nomura, Takayuki Doi

    The Journal of Organic Chemistry　83　(16)　9430-9441　2018/06

    DOI： 10.1021/acs.joc.8b01075 　

  28. Conjugate Addition to Acylketene Acetals Derived from 1,8-Dihydroxynaphthalene and Its Application To Synthesize the Proposed Structure of Spiropreussione A Peer-reviewed

    Hirokazu Tsukamoto, Yumi Nomura, Koichi Fujiwara, Shogo Hanada, Takayuki Doi

    Organic Letters　20　(10)　3140-3143　2018/05

    Publisher: American Chemical Society

    DOI： 10.1021/acs.orglett.8b01259 　

    ISSN： 1523-7052 1523-7060

  29. Synthesis of multiple-substituted dihydrofurans via palladium-catalysed coupling between 2,3-alkadienols and pronucleophiles Peer-reviewed

    Hirokazu Tsukamoto, Kazuya Ito, Takayuki Doi

    Chemical Communications　54　(40)　5102-5105　2018/04

    Publisher: Royal Society of Chemistry

    DOI： 10.1039/c8cc02589d 　

    ISSN： 1364-548X 1359-7345

  30. Total Synthesis and Biological Evaluation of Siladenoserinol A and its Analogues Peer-reviewed

    Masahito Yoshida, Koya Saito, Hikaru Kato, Sachiko Tsukamoto, Takayuki Doi

    Angew Chem Int Ed　57　(18)　5147-5150　2018/03

    Publisher: Wiley-VCH Verlag

    DOI： 10.1002/anie.201801659 　

    ISSN： 1521-3773 1433-7851

  31. Total synthesis and stereochemistry revision of mannopeptimycin aglycone Peer-reviewed

    Shinichiro Fuse, Hiroshi Tanaka, Takashi Takahashi, Takayuki Doi

    J. Syn. Org. Chem. Jpn　75　(12)　1274-1285　2017/12

    Publisher: Society of Synthetic Organic Chemistry

    DOI： 10.5059/yukigoseikyokaishi.75.1274 　

    ISSN： 0037-9980

  32. A small-molecule compound inhibits a collagen-specific molecular chaperone and could represent a potential remedy for fibrosis Peer-reviewed

    Shinya Ito, Koji Ogawa, Koh Takeuchi, Motoki Takagi, Masahito Yoshida, Takatsugu Hirokawa, Shoshiro Hirayama, Kazuo Shin-ya, Ichio Shimada, Takayuki Doi, Naoki Goshima, Tohru Natsume, Kazuhiro Nagata

    JOURNAL OF BIOLOGICAL CHEMISTRY　292　(49)　20076-20085　2017/12

    DOI： 10.1074/jbc.M117.815936 　

    ISSN： 0021-9258

    eISSN： 1083-351X

  33. Systematic Analysis of the Relationship among 3D Structure, Bioactivity, and Membrane Permeability of PF1171F, a Cyclic Hexapeptide with Paralyzing Effects on Silkworms Peer-reviewed

    Yuichi Masuda, Ren Tanaka, A. Ganesan, Takayuki Doi

    JOURNAL OF ORGANIC CHEMISTRY　82　(21)　11447-11463　2017/11

    DOI： 10.1021/acs.joc.7b01975 　

    ISSN： 0022-3263

  34. Stereoselective Synthesis of beta-Amino Acid Derivatives by Asymmetric Mannich Reaction in Flow Peer-reviewed

    Masahito Yoshida, Koji Umeda, Takayuki Doi

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN　90　(10)　1157-1163　2017/10

    DOI： 10.1246/bcsj.20170194 　

    ISSN： 0009-2673

    eISSN： 1348-0634

  35. Facile Synthesis of Pyrrolyl 4-Quinolinone Alkaloids Quinolactacide by 9-AJ-Catalyzed Tandem Acyl Transfer-Cyclization of o-Alkynoylaniline Derivatives Peer-reviewed

    Koya Saito, Masahito Yoshida, Hidehiro Uekusa, Takayuki Doi

    ACS Omega　2　(8)　4370-4381　2017/08

    DOI： 10.1021/acsomega.7b00793 　

  36. Conformation-Based Design and Synthesis of Apratoxin A Mimetics Modified at the alpha,beta-Unsaturated Thiazoline Moiety Peer-reviewed

    Yuichi Onda, Yuichi Masuda, Masahito Yoshida, Takayuki Doi

    JOURNAL OF MEDICINAL CHEMISTRY　60　(15)　6751-6765　2017/08

    DOI： 10.1021/acs.jmedchem.7b00833 　

    ISSN： 0022-2623

    eISSN： 1520-4804

  37. Structural insights into ligand recognition by the lysophosphatidic acid receptor LPA(6) Peer-reviewed

    Reiya Taniguchi, Asuka Inoue, Misa Sayama, Akiharu Uwamizu, Keitaro Yamashita, Kunio Hirata, Masahito Yoshida, Yoshiki Tanaka, Hideaki E. Kato, Yoshiko Nakada-Nakura, Yuko Otani, Tomohiro Nishizawa, Takayuki Doi, Tomohiko Ohwada, Ryuichiro Ishitani, Junken Aoki, Osamu Nureki

    NATURE　548　(7667)　356-+　2017/08

    DOI： 10.1038/nature23448 　

    ISSN： 0028-0836

    eISSN： 1476-4687

  38. Selective inhibition of sterol O-acyltransferase 1 isozyme by beauveriolide III in intact cells Peer-reviewed

    Taichi Ohshiro, Keisuke Kobayashi, Mio Ohba, Daisuke Matsuda, Lawrence L. Rudel, Takashi Takahashi, Takayuki Doi, Hiroshi Tomoda

    SCIENTIFIC REPORTS　7　4163-4163　2017/06

    DOI： 10.1038/s41598-017-04177-8 　

    ISSN： 2045-2322

  39. Synthesis of Spiromamakone A Benzo Analogues via Double Oxa-Michael Addition of 1,8-Dihydroxynaphthalene Peer-reviewed

    Hirokazu Tsukamoto, Shogo Hanada, Koichi Kumasaka, Noritaka Kagaya, Miho Izumikawa, Kazuo Shin-ya, Takayuki Doi

    ORGANIC LETTERS　18　(19)　4848-4851　2016/10

    DOI： 10.1021/acs.orglett.6b02328 　

    ISSN： 1523-7060

    eISSN： 1523-7052

  40. Combinatorial Solid-Phase Synthesis and Biological Evaluation of Cyclodepsipeptide Destruxin B as a Negative Regulator for Osteoclast Morphology Peer-reviewed

    Hiroshi Sato, Masahito Yoshida, Hayato Murase, Hiroshi Nakagawa, Takayuki Doi

    ACS COMBINATORIAL SCIENCE　18　(9)　590-595　2016/09

    DOI： 10.1021/acscombsci.6b00076 　

    ISSN： 2156-8952

    eISSN： 2156-8944

  41. Synthesis of (2S,3R,4R)-3,4-dihydroxyarginine and its inhibitory activity against nitric oxide synthase Peer-reviewed

    Yuichi Masuda, Chitose Maruyama, Kyuichi Kawabata, Yoshimitsu Hamano, Takayuki Doi

    TETRAHEDRON　72　(36)　5602-5611　2016/09

    DOI： 10.1016/j.tet.2016.07.050 　

    ISSN： 0040-4020

  42. Potent Oxazoline Analog of Apratoxin C: Synthesis, Biological Evaluation, and Conformational Analysis Peer-reviewed

    Masahito Yoshida, Yuichi Onda, Yuichi Masuda, Takayuki Doi

    BIOPOLYMERS　106　(4)　404-414　2016/07

    DOI： 10.1002/bip.22781 　

    ISSN： 0006-3525

    eISSN： 1097-0282

  43. Design, Synthesis, and Biological Evaluation of Beauveriolide Analogues Bearing Photoreactive Amino Acids Invited Peer-reviewed

    Yuichi Masuda, Kazumasa Aoyama, Masahito Yoshida, Keisuke Kobayashi, Taichi Ohshiro, Hiroshi Tomoda, Takayuki Doi

    CHEMICAL & PHARMACEUTICAL BULLETIN　64　(7)　754-765　2016/07

    DOI： 10.1248/cpb.c16-00095 　

    ISSN： 0009-2363

  44. Palladium(II)-Catalyzed Annulation of Alkynes with 2-(Cyanomethyl)phenylboronates Leading to 3,4-Disubstituted 2-Naphthalenamines Peer-reviewed

    Hirokazu Tsukamoto, Taishi Ikeda, Takayuki Doi

    JOURNAL OF ORGANIC CHEMISTRY　81　(5)　1733-1745　2016/03

    DOI： 10.1021/acs.joc.5b02378 　

    ISSN： 0022-3263

  45. Solid-Phase Combinatorial Synthesis and Biological Evaluation of Destruxin E Analogues Peer-reviewed

    Masahito Yoshida, Yoshitaka Ishida, Kenta Adachi, Hayato Murase, Hiroshi Nakagawa, Takayuki Doi

    CHEMISTRY-A EUROPEAN JOURNAL　21　(50)　18417-18430　2015/12

    DOI： 10.1002/chem.201502970 　

    ISSN： 0947-6539

    eISSN： 1521-3765

  46. Foxo3a Inhibitors of Microbial Origin, JBIR-141 and JBIR-142 Peer-reviewed

    Teppei Kawahara, Noritaka Kagaya, Yuichi Masuda, Takayuki Doi, Miho Izumikawa, Kumiko Ohta, Atsushi Hirao, Kazuo Shin-ya

    ORGANIC LETTERS　17　(21)　5476-5479　2015/11

    DOI： 10.1021/acs.orglett.5b02842 　

    ISSN： 1523-7060

    eISSN： 1523-7052

  47. Total synthesis of cyclodepsipeptide spiruchostatin A on silyl-linked polymer-support Peer-reviewed

    Masahito Yoshida, Ken-ichi Sasahara, Takayuki Doi

    TETRAHEDRON　71　(40)　7647-7653　2015/10

    DOI： 10.1016/j.tet.2015.07.064 　

    ISSN： 0040-4020

  48. Structure Revision of Similanamide to PF1171C by Total Synthesis Peer-reviewed

    Yuichi Masuda, Ren Tanaka, A. Ganesan, Takayuki Doi

    JOURNAL OF NATURAL PRODUCTS　78　(9)　2286-2291　2015/09

    DOI： 10.1021/acs.jnatprod.5b00643 　

    ISSN： 0163-3864

    eISSN： 1520-6025

  49. Study for diastereoselective aldol reaction in flow: synthesis of (E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid, a key component of cyclodepsipeptide HDAC inhibitors Peer-reviewed

    Takayuki Doi, Hiroyuki Otaka, Koji Umeda, Masahito Yoshida

    TETRAHEDRON　71　(37)　6463-6470　2015/09

    DOI： 10.1016/j.tet.2015.05.051 　

    ISSN： 0040-4020

  50. Pyrrolidine-containing peptides, JBIR-126,-148, and-149, from Streptomyces sp NBRC 111228 Peer-reviewed

    Miho Izumikawa, Teppei Kawahara, Noritaka Kagaya, Hideki Yamamura, Masayuki Hayakawa, Motoki Takagi, Masahito Yoshida, Takayuki Doi, Kazuo Shin-ya

    TETRAHEDRON LETTERS　56　(39)　5333-5336　2015/09

    DOI： 10.1016/j.tetlet.2015.07.080 　

    ISSN： 0040-4039

  51. Asymmetric Total Synthesis of ent-PyripyropeneA Peer-reviewed

    Shinichiro Fuse, Ayako Ikebe, Kazuya Oosumi, Tomoya Karasawa, Keisuke Matsumura, Miho Izumikawa, Kohei Johmoto, Hidehiro Uekusa, Kazuo Shin-ya, Takayuki Doi, Takashi Takahashi

    CHEMISTRY-A EUROPEAN JOURNAL　21　(26)　9454-9460　2015/06

    DOI： 10.1002/chem.201500703 　

    ISSN： 0947-6539

    eISSN： 1521-3765

  52. An Efficient Synthesis of Aurone Derivatives by the Tributylphosphine-catalyzed Regioselective Cyclization of o-Alkynoylphenols Peer-reviewed

    Koya Saito, Masahito Yoshida, Takayuki Doi

    CHEMISTRY LETTERS　44　(2)　141-143　2015/02

    DOI： 10.1246/cl.140910 　

    ISSN： 0366-7022

    eISSN： 1348-0715

  53. Total Synthesis and Structure Elucidation of JBIR-39: A Linear Hexapeptide Possessing Piperazic Acid and gamma-Hydroxypiperazic Acid Residues Peer-reviewed

    Masahito Yoshida, Naoki Sekioka, Miho Izumikawa, Ikuko Kozone, Motoki Takagi, Kazuo Shin-ya, Takayuki Doi

    CHEMISTRY-A EUROPEAN JOURNAL　21　(7)　3031-3041　2015/02

    DOI： 10.1002/chem.201406020 　

    ISSN： 0947-6539

    eISSN： 1521-3765

  54. Asymmetric palladium-catalyzed umpolung cyclization of allylic acetate-aldehyde using formate as a reductant Peer-reviewed

    Hirokazu Tsukamoto, Ayumu Kawase, Takayuki Doi

    CHEMICAL COMMUNICATIONS　51　(38)　8027-8030　2015

    DOI： 10.1039/c5cc02176f 　

    ISSN： 1359-7345

    eISSN： 1364-548X

  55. Total Synthesis of Telomestatin and its Analogues Invited Peer-reviewed

    Takayuki Doi, Masahito Yoshida, Kazuaki Shibata

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN　73　(1)　7-17　2015/01

    DOI： 10.5059/yukigoseikyokaishi.73.3 　

    ISSN： 0037-9980

  56. Total Synthesis and Structure Determination of JBIR-108-A 2-Hydroxy-2-(1-hydroxyethyl)-2,3-dihydro-3(2H)-furanone Isolated from Streptomyces gramineus IR087Pi-4 Peer-reviewed

    Koichi Fujiwara, Hirokazu Tsukamoto, Miho Izumikawa, Takahiro Hosoya, Noritaka Kagaya, Motoki Takagi, Hideki Yamamura, Masayuki Hayakawa, Kazuo Shin-ya, Takayuki Doi

    JOURNAL OF ORGANIC CHEMISTRY　80　(1)　114-132　2015/01

    DOI： 10.1021/jo502198y1J 　

    ISSN： 0022-3263

    eISSN： 1520-6904

  57. SYNTHESIS AND BIOLOGICAL EVALUATION OF C-AROMATAXANE DERIVATIVES AS P-GLYCOPROTEIN-MEDIATED MULTI DRUG RESISTANCE REVERSAL AGENTS Peer-reviewed

    Takayuki Doi, Naoko Yamaguchi, Kosuke Ohsawa, Kazuoki Nakai, Masahito Yoshida, Kazuhiro Satake, Yuji Mitani, Hiroshi Nakagawa, Takashi Takahashi, Toshihisa Ishikawa

    HETEROCYCLES　90　(1)　482-501　2015/01

    DOI： 10.3987/COM-14-S(K)47 　

    ISSN： 0385-5414

    eISSN： 1881-0942

  58. Total Synthesis and Conformational Analysis of Apratoxin C Peer-reviewed

    Yuichi Masuda, Jun Suzuki, Yuichi Onda, Yuta Fujino, Masahito Yoshida, Takayuki Doi

    JOURNAL OF ORGANIC CHEMISTRY　79　(17)　8000-8009　2014/09

    DOI： 10.1021/jo501130b 　

    ISSN： 0022-3263

  59. An Efficient Partial Reduction of alpha,beta-Unsaturated Esters Using DIBAL-H in Flow Peer-reviewed

    Masahito Yoshida, Hiroyuki Otaka, Takayuki Doi

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY　2014　(27)　6010-6016　2014/09

    DOI： 10.1002/ejoc.201402675 　

    ISSN： 1434-193X

    eISSN： 1099-0690

  60. Total Synthesis and Biological Evaluation of PF1171A, C, F, and G, Cyclic Hexapeptides with Insecticidal Activity Peer-reviewed

    Yuichi Masuda, Ren Tanaka, Kenji Kai, A. Ganesan, Takayuki Doi

    JOURNAL OF ORGANIC CHEMISTRY　79　(17)　7844-7853　2014/09

    DOI： 10.1021/jo500861k 　

    ISSN： 0022-3263

  61. Total Synthesis and Stereochemistry Revision of Mannopeptimycin Aglycone Peer-reviewed

    Shinichiro Fuse, Hirotsugu Koinuma, Atsushi Kimbara, Miho Izumikawa, Yuto Mifune, Haiyin He, Kazuo Shin-ya, Takashi Takahashi, Takayuki Doi

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY　136　(34)　12011-12017　2014/08

    DOI： 10.1021/ja505105t 　

    ISSN： 0002-7863

  62. Synthesis of the Biologically Active Natural Product Cyclodepsipeptides Apratoxin A and Its Analogues Invited Peer-reviewed

    Takayuki Doi

    CHEMICAL & PHARMACEUTICAL BULLETIN　62　(8)　735-743　2014/08

    DOI： 10.1248/cpb.c14-00268 　

    ISSN： 0009-2363

  63. A concise total synthesis of biologically active frutinones via tributylphosphine-catalyzed tandem acyl transfer-cyclization Peer-reviewed

    Masahito Yoshida, Koya Saito, Yuta Fujino, Takayuki Doi

    TETRAHEDRON　70　(21)　3452-3458　2014/05

    DOI： 10.1016/j.tet.2014.03.073 　

    ISSN： 0040-4020

  64. Epigallocatechin Gal late Decreases the Micellar Solubility of Cholesterol via Specific Interaction with Phosphatidylcholine Peer-reviewed

    Makoto Kobayashi, Masato Nishizawa, Nao Inoue, Takahiro Hosoya, Masahito Yoshida, Yuichi Ukawa, Yuko M. Sagesaka, Takayuki Doi, Tsutomu Nakayama, Shigenori Kumazawa, Ikuo Ikeda

    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY　62　(13)　2881-2890　2014/04

    DOI： 10.1021/jf405591g 　

    ISSN： 0021-8561

    eISSN： 1520-5118

  65. Scalable Solution-Phase Synthesis of the Biologically Active Cyclodepsipeptide Destruxin E, a Potent Negative Regulator of Osteoclast Morphology Peer-reviewed

    Masahito Yoshida, Hiroshi Sato, Yoshitaka Ishida, Hiroshi Nakagawa, Takayuki Doi

    JOURNAL OF ORGANIC CHEMISTRY　79　(1)　296-306　2014/01

    DOI： 10.1021/jo402437z 　

    ISSN： 0022-3263

  66. Total synthesis and characterization of thielocin B1 as a protein-protein interaction inhibitor of PAC3 homodimer Peer-reviewed

    Takayuki Doi, Masahito Yoshida, Kosuke Ohsawa, Kazuo Shin-ya, Motoki Takagi, Yoshinori Uekusa, Takumi Yamaguchi, Koichi Kato, Takatsugu Hirokawa, Tohru Natsume

    CHEMICAL SCIENCE　5　(5)　1860-1868　2014

    DOI： 10.1039/c3sc53237b 　

    ISSN： 2041-6520

    eISSN： 2041-6539

  67. Synthesis of Hepta-oxazole Macrocyclic Analogues of Telomestatin and Evaluation of Their Telomerase Inhibitory Activities Peer-reviewed

    Kazuaki Shibata, Masahito Yoshida, Takashi Takahashi, Motoki Takagi, Kazuo Shin-ya, Takayuki Doi

    Bulletin of the Chemical Society of Japan　86　(12)　1453-1465　2013/12

    DOI： 10.1246/bcsj.20130198 　

    ISSN： 0009-2673 1348-0634

  68. Alternate Mode of Palladium-Catalyzed Alkynyliminium Ion Cyclizations Affording Stereodefined N-Alkyl-2-alkylidenepyrrolidines Peer-reviewed

    Hirokazu Tsukamoto, Mitsugu Shiraishi, Takayuki Doi

    Organic Letters　15　(23)　5932-5935　2013/11/08

    DOI： 10.1021/ol402685g 　

    ISSN： 1523-7060 1523-7052

  69. Design and synthesis of 2-phenyl-1,4-dioxa-spiro[4.5]deca-6,9-dien-8-ones as potential anticancer agents starting from cytotoxic spiromamakone A Peer-reviewed

    Shinichiro Fuse, Kennichi Inaba, Motoki Takagi, Masahiro Tanaka, Takatsugu Hirokawa, Kohei Johmoto, Hidehiro Uekusa, Kazuo Shin-Ya, Takashi Takahashi, Takayuki Doi

    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY　66　180-184　2013/08

    DOI： 10.1016/j.ejmech.2013.05.030 　

    ISSN： 0223-5234

    eISSN： 1768-3254

  70. A Direct and Mild Formylation Method for Substituted Benzenes Utilizing Dichloromethyl Methyl Ether-Silver Trifluoromethanesulfonate Peer-reviewed

    Kosuke Ohsawa, Masahito Yoshida, Takayuki Doi

    JOURNAL OF ORGANIC CHEMISTRY　78　(7)　3438-3444　2013/04

    DOI： 10.1021/jo400056k 　

    ISSN： 0022-3263

  71. Total Synthesis of Destruxin E and its Derivatives

    YOSHIDA Masahito, ISHIDA Yoshitaka, TAKEUCHI Hisayuki, NAKAGAWA Hiroshi, YASHIRODA Yoko, YOSHIDA Minoru, TAKAGI Motoki, SHIN-YA Kazuo, DOI Takayuki

    Peptide science : proceedings of the ... Japanese Peptide Symposium　2012　95-96　2013/03/01

    ISSN： 1344-7661

  72. The performance of Tohoku University on the innovation of academically driven drug discovery using chemical library Peer-reviewed

    Sugawara Akira, Aoki Junken, Dan Takashi, Shimizu Ritsuko, Suzuki Norio, Kano Kuniyuki, Okudaira Shinichi, Hakoda Akiko, Kaneko Hiroshi, Uchida Takafurni, Nakazawa Toru, Doi Takayuki, Miyata Toshio, Oshima Yoshiteru, Yamamoto Masayuki

    JOURNAL OF PHARMACOLOGICAL SCIENCES　121　50P-50P　2013

    ISSN： 1347-8613

  73. Elucidation of the Active Conformation of Vancomycin Dimers with Antibacterial Activity against Vancomycin-Resistant Bacteria Peer-reviewed

    Jun Nakamura, Hidenori Yamashiro, Sayaka Hayashi, Mami Yamamoto, Kenji Miura, Shu Xu, Takayuki Doi, Hideki Maki, Osamu Yoshida, Hirokazu Arimoto

    CHEMISTRY-A EUROPEAN JOURNAL　18　(40)　12681-12689　2012/10

    DOI： 10.1002/chem.201201211 　

    ISSN： 0947-6539

  74. A highly sensitive fluorescence method reveals the presence of palladium in a cross-coupling reaction mixture not treated with transition metals Peer-reviewed

    Kiyofumi Inamoto, Laura D. Campbell, Takayuki Doi, Kazunori Koide

    TETRAHEDRON LETTERS　53　(25)　3147-3148　2012/06

    DOI： 10.1016/j.tetlet.2012.04.043 　

    ISSN： 0040-4039

  75. Comprehensive predictions of target proteins based on protein-chemical interaction using virtual screening and experimental verifications Peer-reviewed

    Hiroki Kobayashi, Hiroko Harada, Masaomi Nakamura, Yushi Futamura, Akihiro Ito, Minoru Yoshida, Shun-Ichiro Iemura, Kazuo Shin-Ya, Takayuki Doi, Takashi Takahashi, Tohru Natsume, Masaya Imoto, Yasubumi Sakakibara

    BMC Chemical Biology　12　2　2012

    DOI： 10.1186/1472-6769-12-2 　

    ISSN： 1472-6769

  76. Conformationally restricted analog and biotin-labeled probe based on beauveriolide III Peer-reviewed

    Takayuki Doi, Terushige Muraoka, Taichi Ohshiro, Daisuke Matsuda, Masahito Yoshida, Takashi Takahashi, Satoshi Omura, Hiroshi Tomoda

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS　22　(1)　696-699　2012/01

    DOI： 10.1016/j.bmcl.2011.10.045 　

    ISSN： 0960-894X

  77. Development of a Near Infrared Fluorescence Labeling Reagent: Synthesis of Indole-Functionalized Indocyanine Green Derivatives Peer-reviewed

    Takayuki Doi, Koya Oikawa, Jun Suzuki, Masahito Yoshida, Nobuhiko Iki

    SYNLETT　(2)　306-310　2012/01

    DOI： 10.1055/s-0031-1290139 　

    ISSN： 0936-5214

  78. Use of dimethyl carbonate as a solvent greatly enhances the biaryl coupling of aryl iodides and organoboron reagents without adding any transition metal catalysts Peer-reviewed

    Kiyofumi Inamoto, Chisa Hasegawa, Kou Hiroya, Yoshinori Kondo, Takao Osako, Yasuhiro Uozumi, Takayuki Doi

    CHEMICAL COMMUNICATIONS　48　(23)　2912-2914　2012

    DOI： 10.1039/c2cc17401d 　

    ISSN： 1359-7345

  79. Tandem-type Pd(II)-catalyzed oxidative Heck reaction/intramolecular C-H amidation sequence: a novel route to 4-aryl-2-quinolinones Peer-reviewed

    Kiyofumi Inamoto, Junpei Kawasaki, Kou Hiroya, Yoshinori Kondo, Takayuki Doi

    CHEMICAL COMMUNICATIONS　48　(36)　4332-4334　2012

    DOI： 10.1039/c2cc30600j 　

    ISSN： 1359-7345

    eISSN： 1364-548X

  80. A concise synthesis of 3-aroylflavones via Lewis base 9-azajulolidine-catalyzed tandem acyl transfer-cyclization Peer-reviewed

    Masahito Yoshida, Koya Saito, Yuta Fujino, Takayuki Doi

    CHEMICAL COMMUNICATIONS　48　(96)　11796-11798　2012

    DOI： 10.1039/c2cc37015h 　

    ISSN： 1359-7345

  81. Regioselective synthesis of flavone derivatives via DMAP-catalyzed cyclization of o-alkynoylphenols Invited Peer-reviewed

    Masahito Yoshida, Yuta Fujino, Koya Saito, Takayuki Doi

    TETRAHEDRON　67　(51)　9993-9997　2011/12

    DOI： 10.1016/j.tet.2011.09.063 　

    ISSN： 0040-4020

  82. 31 Total Synthesis of Mannopeptimycin Aglycon(Oral Presentation)

    Fuse Shinichiro, Koinuma Hirotsugu, Kinbara Atsushi, Doi Takayuki, Takahashi Takashi

    Symposium on the Chemistry of Natural Products, symposium papers　(53)　181-186　2011/09/02

    Publisher: Symposium on the chemistry of natural products

    DOI： 10.24496/tennenyuki.53.0_181 　

    More details Close

    In 2002, mannopeptimycins 1-5 are isolated from Streptomyces hygroscopicus LL-AC98 as potent antibiotics by He and his co-workers. Mannnopeptimycins exhibited antimicrobial activity against Gram-positive bacteria, including methicillin-resistant streptococci and vancomycin-resistant enterococci. Mannopeptimycins consist of 6 amino acids including 3 unnatural residues. Aiha-A (α-amino-β[4'-(2' -imino-imida -zolidiny1)]-(β-hydroxypropionic acid-A) and Aiha-B are unnatural cyclic guanidine containing amino acids which are only found in mannopeptimycins. For further elucidation of mechanism of action and structure-activity relationships of mannnopeptimycins, the development of efficient synthetic methodology is important. However, there has been no synthetic report for mannopeptimycin aglycon. Only recently, syntheses of Aiha-A and Aiha-B were disclosed by two groups. Herein, we wish to report the total synthesis of proposed structure of mannopeptimycin aglycon 6. Aiha-A and Aiha-B were synthesized from the common synthetic intermediate 19 via asymmetric aldol reaction with aldehyde 17. Threo product 21 smoothly cyclized to afford the corresponding N,0-cyclic acetal 22 in the presence of silica-gel. On the other hand, erythro product 20 did not form the N,0-cyclic acetal due to steric repulsion. 20 and 22 were readily separated by using silica gel column chromatography. A cyclic guanidine moiety was introduced using Goodman reagent to afford Aiha A 26 and Aiha B 28, respectively. L-Ser 8 was coupled with Aiha-B 28 using HATU. The following condensation with Aiha-A 26 using HATU afforded the undesired product 31. We could overcome the problem by employing PyBOP as a condensation agent. The coupling between 25 and 30, and the crucial macrolactamization proceeded well using HATU. Global deprotection under hydrogenation condition afforded the aimed product 6 in good yield. The structure was confirmed by ^1H NMR, ^<13>C NMR, ^1H-^1H COSY, HMBC, HSQC, MS analyses.

  83. Synthesis of gamma-Benzopyranone by TfOH-Promoted Regioselective Cyclization of o-Alkynoylphenols Peer-reviewed

    Masahito Yoshida, Yuta Fujino, Takayuki Doi

    ORGANIC LETTERS　13　(17)　4526-4529　2011/09

    DOI： 10.1021/ol2016934 　

    ISSN： 1523-7060

    eISSN： 1523-7052

  84. JBIR-56 and JBIR-57, 2(1H)-Pyrazinones from a Marine Sponge-Derived Streptomyces sp SpD081030SC-03 Peer-reviewed

    Keiichiro Motohashi, Kennichi Inaba, Shinichiro Fuse, Takayuki Doi, Miho Izumikawa, Shams Tabrez Khan, Motoki Takagi, Takashi Takahashi, Kazuo Shin-ya

    JOURNAL OF NATURAL PRODUCTS　74　(7)　1630-1635　2011/07

    DOI： 10.1021/np200386c 　

    ISSN： 0163-3864

    eISSN： 1520-6025

  85. Total Synthesis of Optically Active Lycopladine A by Utilizing Diastereoselective Protection of Carbonyl Group in a 1,3-Cyclohexanedione Derivative Peer-reviewed

    Kou Hiroya, Yoshihiro Suwa, Yusuke Ichihashi, Kiyofumi Inamoto, Takayuki Doi

    JOURNAL OF ORGANIC CHEMISTRY　76　(11)　4522-4532　2011/06

    DOI： 10.1021/jo200418y 　

    ISSN： 0022-3263

  86. Ribosomal Synthesis of Backbone-Macrocyclic Peptides Containing gamma-Amino Acids Peer-reviewed

    Yukinori Ohshiro, Eiji Nakajima, Yuki Goto, Shinichiro Fuse, Takashi Takahashi, Takayuki Doi, Hiroaki Suga

    CHEMBIOCHEM　12　(8)　1183-1187　2011/05

    DOI： 10.1002/cbic.201100104 　

    ISSN： 1439-4227

  87. Isolation of New Hexapeptides －JBIR-39 and JBIR-40－ from a Marine Sponge-Derived Streptomyces sp. Sp080513SC-24 Peer-reviewed

    Ikuko Kozone, Miho Izumikawa, Keiichiro Motohashi, Aya Nagai, Masahito Yoshida, Takayuki Doi, Motoki Takagi, Kazuo Shin-ya

    Journal of Marine Science: Research & Development　1　(1)　1000101-1000101　2011/02

    DOI： 10.4172/2155-9910.1000101 　

  88. Solid-phase Total Synthesis of (-)-Apratoxin A and Its Analogues and Their Biological Evaluation Peer-reviewed

    Takayuki Doi, Yoshitaka Numajiri, Takashi Takahashi, Motoki Takagi, Kazuo Shin-ya

    CHEMISTRY-AN ASIAN JOURNAL　6　(1)　180-188　2011/01

    DOI： 10.1002/asia.201000549 　

    ISSN： 1861-4728

    eISSN： 1861-471X

  89. (S)-Stereoisomer of telomestatin as a potent G-quadruplex binder and telomerase inhibitor Peer-reviewed

    Takayuki Doi, Kazuaki Shibata, Masahito Yoshida, Motoki Takagi, Masayuki Tera, Kazuo Nagasawa, Kazuo Shin-ya, Takashi Takahashi

    ORGANIC & BIOMOLECULAR CHEMISTRY　9　(2)　387-393　2011

    DOI： 10.1039/c0ob00513d 　

    ISSN： 1477-0520

    eISSN： 1477-0539

  90. Total synthesis of spiruchostatin B aided by an automated synthesizer Peer-reviewed

    Shinichiro Fuse, Kumiko Okada, Yusuke Iijima, Asami Munakata, Kazuhiro Machida, Takashi Takahashi, Motoki Takagi, Kazuo Shin-ya, Takayuki Doi

    ORGANIC & BIOMOLECULAR CHEMISTRY　9　(10)　3825-3833　2011

    DOI： 10.1039/c0ob01169j 　

    ISSN： 1477-0520

    eISSN： 1477-0539

  91. Anti-Influenza Virus Compound from Streptomyces sp RI18 Peer-reviewed

    Motoki Takagi, Keiichiro Motohashi, Aya Nagai, Miho Izumikawa, Masahiro Tanaka, Shinichiro Fuse, Takayuki Doi, Keiichiro Iwase, Atsushi Kawaguchi, Kyosuke Nagata, Takashi Takahashi, Kazuo Shin-ya

    ORGANIC LETTERS　12　(20)　4664-4666　2010/10

    DOI： 10.1021/ol102007d 　

    ISSN： 1523-7060

    eISSN： 1523-7052

  92. Use of Molecular Oxygen as a Reoxidant in the Synthesis of 2-Substituted Benzothiazoles via Palladium-Catalyzed C-H Functionalization/Intramolecular C-S Bond Formation Peer-reviewed

    Kiyofumi Inamoto, Chisa Hasegawa, Junpei Kawasaki, Kou Hiroya, Takayuki Doi

    ADVANCED SYNTHESIS & CATALYSIS　352　(14-15)　2643-2655　2010/10

    DOI： 10.1002/adsc.201000604 　

    ISSN： 1615-4150

  93. Synthesis, Structure Determination and Biological Evaluation of Destruxin E

    Yoshida M., Takeuchi H., Ishida Y., Yashiroda Y., Yoshida M., Takagi M., Shin-ya K., Doi T.

    Symposium on the Chemistry of Natural Products, symposium papers　(52)　361-366　2010/09/01

    Publisher: Symposium on the chemistry of natural products

    DOI： 10.24496/tennenyuki.52.0_361 　

    More details Close

    Destruxin E (1) is a 19-membered cyclic depsipeptide, consisting of five amino acids (proline, isoleucine, NMe-valine, NMe-alanine and β-alanine) and epoxide-containing α-hydroxy acid. It was isolated from a culture medium of the strain of Metalizium anisopliae by Pais et al. in 1981. 1 exhibits strongly inhibition of V-ATPase (IC_<50> 0.4μM) that is localized on the membranes enclosing the organelles such as the lysosomes and function to acidify a wide array of intracellular compartments. V-ATPases have also an important role for the control of tumor microenvironment by proton extrusion, therefore the inhibitor of V-ATPase can be a drug candidate for the cancer therapy. To elucidate the structure-activity relationships involving destruxin E (1), we are interested in the total synthesis and the assignment of the streochemistry of the epoxide. The key intermediate 5a was prepared from chiral lactone 6a, which was prepared by Evans asymmetric allylation, followed by dihydroxylation. The cyclization precursor 4a was obtained by solid-phase peptide synthesis. Macrolactonization of 4a was performed utilizing MNBA/DMAPO to yield macrocycle 3a. Finally, formation of the epoxide in the side chain via 3 steps furnished destruxin E (1), whose spectral data were in good agreement with those of the natural product. We have also found that natural and synthetic destruxin E exhibit 10-fold greater V-ATPase inhibitory acgtivity than epi-destruxin E (2). Our synthetic study reveals not only the possibility of library synthesis, but also the stereochemistry of the epoxide is quite important for inducint V-ATPase inhibitory activity.

  94. Stabilization and visualization of G-quadruplex by using telomestatin derivatives

    Tera Masayuki, Iida Keisuke, Doi Takayuki, Seimiya Hiruyuki, Shin-ya Kazuo, Nagasawa Kazuo

    Symposium on the Chemistry of Natural Products, symposium papers　(52)　331-335　2010/09/01

    Publisher: Symposium on the chemistry of natural products

    DOI： 10.24496/tennenyuki.52.0_331 　

    More details Close

    Telomestatin (TMS; 1) is a natural pruduct that was isolated from Streptomyces anulatus 3533-SV4 by screeing with the telomeric repeat amplification protocol (TRAP) assay. The macrocyclic polyoxazole structure of TMS was reported to interact with telomeres, strongly stabilizing the G-quadruplex structure. Therefore, TMS is widely used as a standard G-quadruplex binder for exploring various functions. However, TMS is not available in great quantity, and many synthetic approaches have been explored. Here, we designed L1H1-7OTD (2), which is a macrocyclic heptaoxazole with an aminobutyl group side chain. We anticipated that the increased planarity of the macrocyclic structure relative to the 6OTDs would allow strong intercalation with G-quadruplexes through π-π interactions. The amino group in 2 was also expected to stabilize the G-quqdruplex structure efficiently through interaction with phosphste groups in the G-quadruplex. Furthermore, a BODIPY-labeled macrocclic heptaoxazole, L1BOD-7OTD (4), was developed as a fluorescent ligand for G-quadruplexes. The results of the study show that 4 both selectively induces the formation of intramolecular G-quadruplexes from some G-quadruplex forming oligonucleotides (GFOs). In addition, the labelled macrocyclic heptaozaxole strongly binds to and stabilizes intramolecular G-quadruplexes. Moreover, this substance can be used to directly visualie the G-quadruplexes in the form of green fluorescence.

  95. Synthesis, Structure Determination, and Biological Evaluation of Destruxin E Peer-reviewed

    Masahito Yoshida, Hisayuki Takeuchi, Yoshitaka Ishida, Yoko Yashiroda, Minoru Yoshida, Motoki Takagi, Kazuo Shin-ya, Takayuki Doi

    ORGANIC LETTERS　12　(17)　3792-3795　2010/09

    DOI： 10.1021/ol101449x 　

    ISSN： 1523-7060

  96. Facile Conversion of Thioamides into the Corresponding Amides in the Presence of Tetrabutylammonium Bromide Peer-reviewed

    Kiyofumi Inamoto, Mitsugu Shiraishi, Kou Hiroya, Takayuki Doi

    SYNTHESIS-STUTTGART　(18)　3087-3090　2010/09

    DOI： 10.1055/s-0030-1258154 　

    ISSN： 0039-7881

  97. Construction of the ABC Ring System of Taxanes via Stereoselective One-Pot Three-Component Coupling and Intramolecular Alkylation of a Protected Cyanohydrin Ether Peer-reviewed

    Takayuki Serizawa, Shigeru Miyamoto, Shinichiro Fuse, Takayuki Doi, Takashi Takahashi

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN　83　(8)　942-949　2010/08

    DOI： 10.1246/bcsj.20090341 　

    ISSN： 0009-2673

    eISSN： 1348-0634

  98. Synthesis of bicyclic enediynes that possess a photosensitive triggering device and exhibit strong DNA cleaving activity Peer-reviewed

    Hiroshi Tanaka, Yoshikazu Tanaka, Masafumi Minoshima, Sho Yamaguchi, Shinichiro Fuse, Takayuki Doi, Susumu Kawauchi, Hiroshi Sugiyama, Takashi Takahashi

    Chemical Communications　46　(32)　5942-5944　2010/07

    DOI： 10.1039/C0CC01286F, 　

  99. Evolved Diversification of a Modular Natural Product Pathway: Apratoxins F and G, Two Cytotoxic Cyclic Depsipeptides from a Palmyra Collection of Lyngbya bouillonii Peer-reviewed

    Kevin Tidgewell, Niclas Engene, Tara Byrum, Joseph Media, Takayuki Doi, Fred A. Valeriote, William H. Gerwick

    CHEMBIOCHEM　11　(10)　1458-1466　2010/07

    DOI： 10.1002/cbic.201000070 　

    ISSN： 1439-4227

    eISSN： 1439-7633

  100. Facile synthesis of asymmetric quaternary centers based on diastereoselective protection of the carbonyl group at the symmetrical position Peer-reviewed

    Kou Hiroya, Yusuke Ichihashi, Yoshihiro Suwa, Tetsuro Ikai, Kiyofumi Inamoto, Takayuki Doi

    TETRAHEDRON LETTERS　51　(29)　3728-3731　2010/07

    DOI： 10.1016/j.tetlet.2010.05.010 　

    ISSN： 0040-4039

  101. Palladium-Catalyzed Intramolecular Amidation of C(sp(2))-H Bonds: Synthesis of 4-Aryl-2-quinolinones Peer-reviewed

    Kiyofumi Inamoto, Tadataka Saito, Kou Hiroya, Takayuki Doi

    JOURNAL OF ORGANIC CHEMISTRY　75　(11)　3900-3903　2010/06

    DOI： 10.1021/jo100557s 　

    ISSN： 0022-3263

  102. Derivatization of a tris-oxazole using Pd-catalyzed coupling reactions of a 5-bromooxazole moiety Peer-reviewed

    Kazuaki Shibata, Masahito Yoshida, Takayuki Doi, Takashi Takahashi

    TETRAHEDRON LETTERS　51　(13)　1674-1677　2010/03

    DOI： 10.1016/j.tetlet.2010.01.064 　

    ISSN： 0040-4039

  103. パラジウム触媒による炭素－水素結合官能基化 ～インダゾール，インドール，ベンゾチオフェン，ベンゾチアゾールの環構築～ Invited Peer-reviewed

    Kiyofumi Inamoto, Kou Hiroya, Takayuki Doi

    Farumashia,The Pharmaceutical Society of Japan　46　(3)　229-234　2010

  104. Synthesis of chiral polyazamacrocycles of variable ring size Peer-reviewed

    Seiji Kamioka, Sakae Sugiyama, Takashi Takahashia, Takayuki Doi

    ORGANIC & BIOMOLECULAR CHEMISTRY　8　(11)　2529-2536　2010

    DOI： 10.1039/c001228a 　

    ISSN： 1477-0520

  105. Solid-phase combinatorial syntheses of mesomorphic 4-alkoxyphenyl 4-alkoxybenzoylaminobenzoates Peer-reviewed

    Akira Mori, Issei Akahoshi, Masashi Hashimoto, Takayuki Doi, Takashi Takahashi

    LIQUID CRYSTALS　37　(11)　1361-1372　2010

    DOI： 10.1080/02678292.2010.515040 　

    ISSN： 0267-8292

  106. Continuous-flow synthesis of vitamin D-3 Peer-reviewed

    Shinichiro Fuse, Nobutake Tanabe, Masahito Yoshida, Hayato Yoshida, Takayuki Doi, Takashi Takahashi

    CHEMICAL COMMUNICATIONS　46　(46)　8722-8724　2010

    DOI： 10.1039/c0cc02239j 　

    ISSN： 1359-7345

  107. An Efficient Synthesis of a Cyclic Ether Key Intermediate for 9-Membered Masked Enediyne Using an Automated Synthesizer Peer-reviewed

    Yoshikazu Tanaka, Shinichiro Fuse, Hiroshi Tanaka, Takayuki Doi, Takashi Takahashi

    ORGANIC PROCESS RESEARCH & DEVELOPMENT　13　(6)　1111-1121　2009/11

    DOI： 10.1021/op9002455 　

    ISSN： 1083-6160

  108. Total Synthesis and Biological Evaluation of (R)- and (S)-Telomestatin and Analogue Synthesis Utilizing a 5-Bromooxazole Derivative

    Shibata Kazuaki, Yoshida Masahito, Doi Takayuki, Takagi Motoki, Tera Masayuki, Nagasawa Kazuo, Shin-ya Kazuo, Takahashi Takashi

    Symposium on the Chemistry of Natural Products, symposium papers　(51)　127-132　2009/09/01

    Publisher: Symposium on the chemistry of natural products

    DOI： 10.24496/tennenyuki.51.0_127 　

    More details Close

    Telomestatin, isolated from Streptomyces anulatus 3533-SV4, is a potent specific telomerase inhibitor. The unique macrocyclic structure of telomestatin consists of the macrocyclic linkage of two methyloxazoles, five oxazoles and one thiazoline ring. Because of the unique chemical structure along with its unusual and potent biological activity, telomestatin is an attractive synthetic target and a candidate for the design of analogues relevant to anti-cancer drug development. The synthesis of telomestatin derivatives and their biological evaluation are presented. Initially, we achieved the total synthesis of (S)-telomestatin and evaluated its biological activity by telomeric repeat amplification protocol. It was found that (S)-telomestatin is more potent than the natural product, (R)-telomestatin. Toward the further diversity-oriented synthesis of telomestatin, we examined palladium-catalzed cross-coupling reacton of 12 that is the macrocyclic key intermediate containing 5-bromooxazole. We found that the cross-coupling r ea ctions such as Suzuki-Miyaura reactoin of 12 with several aryl boronic acids proceeded under mild conditions leading to the corresponding telomestatin derivatives in moderate yields.

  109. Development of Diastereoselective Birch Reduction-Alkylation Reactions of Bi- and Tricyclic beta-Alkoxy-alpha,beta-unsaturated Ketones Peer-reviewed

    Kou Hiroya, Yusuke Ichihashi, Ai Furutono, Kiyofumi Inamoto, Takao Sakamoto, Takayuki Doi

    JOURNAL OF ORGANIC CHEMISTRY　74　(17)　6623-6630　2009/09

    DOI： 10.1021/jo901094x 　

    ISSN： 0022-3263

  110. Stereoselective one-pot three-component coupling approach towards the synthesis of the AC ring system of taxanes Peer-reviewed

    Takayuki Serizawa, Shigeru Miyamoto, Yoshitaka Numajiri, Shinichiro Fuse, Takayuki Doi, Takashi Takahashi

    TETRAHEDRON LETTERS　50　(26)　3408-3410　2009/07

    DOI： 10.1016/j.tetlet.2009.02.149 　

    ISSN： 0040-4039

  111. A solid-phase total synthesis of the cyclic depsipeptide HDAC inhibitor spiruchostatin A Peer-reviewed

    Yusuke Iijima, Asami Munakata, Kazuo Shin-ya, A. Ganesan, Takayuki Doi, Takashi Takahashi

    TETRAHEDRON LETTERS　50　(24)　2970-2972　2009/06

    DOI： 10.1016/j.tetlet.2009.04.005 　

    ISSN： 0040-4039

  112. Chiral Tetraazamacrocycles Having Four Pendant-Arms Peer-reviewed

    Seiji Kamioka, Takashi Takahashi, Susumu Kawauchi, Hiroaki Adachi, Yusuke Mori, Kotaro Fujii, Hidehiro Uekusa, Takayuki Doi

    ORGANIC LETTERS　11　(11)　2289-2292　2009/06

    DOI： 10.1021/ol9005954 　

    ISSN： 1523-7060

  113. The Selectivity of Beauveriolide Derivatives in Inhibition Toward the Two Isozymes of Acyl-CoA: Cholesterol Acyltransferase Peer-reviewed

    aichi Ohshiro, Daisuke Matsuda, Kenichiro Nagai, Takayuki Doi, Toshiaki Sunazuka, Takashi Takahashi, Lawrence Lee Rudel, Satoshi Omura, Hiroshi Tomoda

    Chemical & Pharmaceutical Bulletin　57　(4)　377-381　2009/05

    DOI： 10.1248/cpb.57.377 　

    ISSN： 0009-2363 1347-5223

  114. N-Heterocyclic Carbene Derived Nickel-Pincer Complexes: Efficient and Applicable Catalysts for Suzuki-Miyaura Coupling Reactions of Aryl/Alkenyl Tosylates and Mesylates Peer-reviewed

    Jun-ichi Kuroda, Kiyofumi Inamoto, Kou Hiroya, Takayuki Doi

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY　2009　(14)　2251-2261　2009/05

    DOI： 10.1002/ejoc.200900067 　

    ISSN： 1434-193X

  115. Synthesis of the core ring system of awajanomycin from N-Boc-3-methoxycarbonyl-2-pyridinone Peer-reviewed

    Kou Hiroya, Kei Kawamoto, Kiyofumi Inamoto, Takao Sakamoto, Takayuki Doi

    TETRAHEDRON LETTERS　50　(18)　2115-2118　2009/05

    DOI： 10.1016/j.tetlet.2009.02.141 　

    ISSN： 0040-4039

  116. JBIR-12, a novel antioxidative agent from Penicillium sp NBRC 103941 Peer-reviewed

    Miho Izumikawa, Aya Nagai, Takayuki Doi, Motoki Takagi, Kazuo Shin-ya

    JOURNAL OF ANTIBIOTICS　62　(4)　177-180　2009/04

    DOI： 10.1038/ja.2009.13 　

    ISSN： 0021-8820

  117. Pincer-type bis(carbene)-derived complexes of nickel(II): Synthesis, structure, and catalytic activity Peer-reviewed

    Kiyofumi Inamoto, Jun-ichi Kuroda, Eunsang Kwon, Kou Hiroya, Takayuki Doi

    JOURNAL OF ORGANOMETALLIC CHEMISTRY　694　(3)　389-396　2009/02

    DOI： 10.1016/j.jorganchem.2008.11.003 　

    ISSN： 0022-328X

  118. Synthesis of a Potent G-Quadruplex-Binding Macrocyclic Heptaoxazole Peer-reviewed

    Masayuki Tera, Keisuke Lida, Hiromichi Ishizuka, Motoki Takagi, Masami Suganuma, Takayuki Doi, Kazuo Shin-ya, Kazuo Nagasawa

    CHEMBIOCHEM　10　(3)　431-+　2009/02

    DOI： 10.1002/cbic.200800563 　

    ISSN： 1439-4227

  119. Solid-phase combinatorial synthesis of ester-type banana-shaped molecules by sequential palladium-catalyzed carbonylation Peer-reviewed

    Masahito Yoshida, Takayuki Doi, Sungmin Kang, Junji Watanabe, Takashi Takahashi

    CHEMICAL COMMUNICATIONS　2009　(19)　2756-2758　2009

    DOI： 10.1039/b901788g 　

    ISSN： 1359-7345

    eISSN： 1364-548X

  120. Total Synthesis of (-)-Apratoxin A, 34-Epimer, and Its Oxazoline Analogue Peer-reviewed

    Yoshitaka Numajiri, Takashi Takahashi, Takayuki Doi

    Chemistry-An Asian Journal　4　(1)　111-125　2009

    DOI： 10.1002/asia.200800365 　

    ISSN： 1861-4728

  121. Total synthesis of largazole and its biological evaluation Peer-reviewed

    Yoshitaka Numajiri, Takashi Takahashi, Motoki Takagi, Shin-Ya Kazuo, Takayuki Doi

    Synlett　(16)　2483-2486　2008/10/01

    DOI： 10.1055/s-2008-1078263 　

    ISSN： 0936-5214

  122. Combinatorial synthesis of RGD model cyclic peptides utilizing a palladium-catalyzed carbonylative macrolactamization on a polymer support Peer-reviewed

    Seiji Kamioka, Sayaka Shimazu, Takayuki Doi, Takashi Takahashi

    JOURNAL OF COMBINATORIAL CHEMISTRY　10　(5)　681-690　2008/09

    DOI： 10.1021/cc800089m 　

    ISSN： 1520-4766

  123. Synthesis and biological evaluation of a focused library of beauveriolides Peer-reviewed

    Kenichiro Nagai, Takayuki Doi, Taichi Ohshiro, Toshiaki Sunazuka, Hiroshi Tomoda, Takashi Takahashi, Satoshi Omura

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS　18　(15)　4397-4400　2008/08

    DOI： 10.1016/j.bmcl.2008.06.054 　

    ISSN： 0960-894X

  124. A synthesis of RGD model cyclic peptide by palladium-catalyzed carbonylative macrolactamization Peer-reviewed

    Takayuki Doi, Seiji Kamioka, Sayaka Shimazu, Takashi Takahashi

    ORGANIC LETTERS　10　(5)　817-819　2008/03

    DOI： 10.1021/ol702965r 　

    ISSN： 1523-7060

  125. A New Approach to 3-Substituted Indoles through Palladium-Catalyzed C-H Activation Followed by Intramolecular Amination Reaction of Enamines Peer-reviewed

    Kiyofumi Inamoto, Tadataka Saito, Kou Hiroya, Takayuki Doi

    Synlett　(20)　3157-3162　2008

    DOI： 10.1055/s-0028-1087413 　

    ISSN： 0936-5214

  126. Palladium-Catalyzed Synthesis of 2-Substituted Benzothiazoles via a C-H Functionalization/Intramolecular C-S Bond Formation Process Peer-reviewed

    Kiyofumi Inamoto, Chisa Hasegawa, Kou Hiroya, Takayuki Doi

    Organic Letters　10　(22)　5147-5150　2008

    DOI： 10.1021/ol802033p 　

    ISSN： 1523-7060

  127. Palladium-Catalysed Direct Synthesis of Benzo[b]thiophenes from Thioenols Peer-reviewed

    Kiyofumi Inamoto, Yukari Arai, Kou Hiroya, Takayuki Doi

    Chemical Communications　(43)　5529-5531　2008

    DOI： 10.1039/b811362a 　

    ISSN： 1359-7345

  128. Sequential palladium-catalyzed coupling reactions on solid-phase Peer-reviewed

    Takayuki Doi, Hitoshi Inoue, Masatoshi Tokita, Junji Watanabe, Takashi Takahashi

    JOURNAL OF COMBINATORIAL CHEMISTRY　10　(1)　135-141　2008/01

    DOI： 10.1021/cc7000925 　

    ISSN： 1520-4766

  129. Discovery and combinatorial synthesis of fungal metabolites beauveriolides, novel antiatherosclerotic agents Peer-reviewed

    Hiroshi Tomoda, Takayuki Doi

    ACCOUNTS OF CHEMICAL RESEARCH　41　(1)　32-39　2008/01

    DOI： 10.1021/ar7001171b 　

    ISSN： 0001-4842

  130. Absolute structure of prunustatin A, a novel GRP78 molecular chaperone down-regulator

    Yukiko Umeda, Kazuo Furihata, Shohei Sakuda, Hiromichi Nagasawa, Ken Ishigami, Hidenori Watanabe, Miho Izumikawa, Motoki Takagi, Takayuki Doi, Yoichi Nakao, Kazuo Shin-ya

    Organic Letters　9　(21)　4239-4242　2007/10/11

    DOI： 10.1021/ol7017856 　

    ISSN： 1523-7060

  131. A Novel nuclear export inhibitor JBIR-02, a new piericidin discovered from streptomyces sp ML55 Peer-reviewed

    Jun-ya Ueda, Takushi Togashi, Susumu Matukura, Aya Nagai, Takuji Nakashima, Hisayuki Komaki, Kozue Anzai, Shigeaki Harayama, Takayuki Doi, Takashi Takahashi, Tohru Natsume, Yasutomo Kisu, Naoki Goshima, Nobuo Nomura, Motoki Takagi, Kazuo Shin-ya

    JOURNAL OF ANTIBIOTICS　60　(7)　459-462　2007/07

    DOI： 10.1038/ja.2007.59 　

    ISSN： 0021-8820

  132. Design and synthesis of telomestatin derivatives and their inhibitory activity of telomerase Peer-reviewed

    Tera Masayuki, Sohtome Yoshihiro, Ishizuka Hiromichi, Doi Takayuki, Takagi Motoki, Kazuo Shin-ya, Nagasawa Kazuo

    HETEROCYCLES　69　(1)　505-+　2006/12/01

    DOI： 10.3987/COM-06-S(O)38 　

    ISSN： 0385-5414

  133. Absolute stereochemistry of fungal beauveriolide III and ACAT inhibitory activity of four stereoisomers. Peer-reviewed

    Ohshiro T, Namatame I, Nagai K, Sekiguchi T, Doi T, Takahashi T, Akasaka K, Rudel LL, Tomoda H, Omura S

    The Journal of organic chemistry　71　(20)　7643-7649　2006/09

    DOI： 10.1021/jo0611667 　

    ISSN： 0022-3263

  134. Total synthesis of (R)-telomestatin Peer-reviewed

    Takayuki Doi, Masahito Yoshida, Kazuo Shin-ya, Takashi Takahashi

    ORGANIC LETTERS　8　(18)　4165-4167　2006/08

    DOI： 10.1021/ol061793i 　

    ISSN： 1523-7060

    eISSN： 1523-7052

  135. Solid-phase combinatorial synthesis of aeruginosin derivatives and their biological evaluation Peer-reviewed

    Takayuki Doi, Yoichiro Hoshina, Hiroyuki Mogi, Yoshifumi Yamada, Takashi Takahashi

    JOURNAL OF COMBINATORIAL CHEMISTRY　8　(4)　571-582　2006/07

    DOI： 10.1021/cc0600270 　

    ISSN： 1520-4766

  136. A total synthesis of spiruchostatin A Peer-reviewed

    Takayuki Doi, Yusuke Iijima, Kazuo Shin-Ya, A. Ganesan, Takashi Takahashi

    Tetrahedron Letters　47　(7)　1177-1180　2006/02/13

    DOI： 10.1016/j.tetlet.2005.12.031 　

    ISSN： 0040-4039

  137. Regio- and stereocontrolled Diels-Alder reaction tethered by Asp-Thr dipeptide Peer-reviewed

    Takayuki Doi, Yuko Miura, Susumu Kawauchi, Takashi Takahashi

    Chemical Communications　(39)　4908-4910　2005/10/21

    DOI： 10.1039/b509156j 　

    ISSN： 1359-7345

  138. Odd-even behavior of ferroelectricity and antiferroelectricity in two homologous series of bent-core mesogens

    SK Lee, S Heo, JG Lee, KT Kang, K Kumazawa, K Nishida, Y Shimbo, Y Takanishi, J Watanabe, T Doi, T Takahashi, H Takezoe

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY　127　(31)　11085-11091　2005/08

    DOI： 10.1021/ja052315q 　

    ISSN： 0002-7863

  139. Synthesis and evaluation of 3D templates based on a taxane skeleton to circumvent P-glycoprotein-associated multidrug resistance of cancer Peer-reviewed

    T Takahashi, K Nakai, T Doi, M Yasunaga, H Nakagawa, T Ishikawa

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS　15　(10)　2601-2605　2005/05

    DOI： 10.1016/j.bmcl.2005.03.038 　

    ISSN： 0960-894X

  140. Novel unsymmetrical achiral banana-shaped molecules having different lengths of alkyl terminal chains Peer-reviewed

    Kumiko Ogino, Sungmin Kang, Takayuki Doi, Takashi Takahashi, Hideo Takezoe, Junji Watanabe

    Chemistry Letters　34　(3)　450-451　2005/03/05

    DOI： 10.1246/cl.2005.450 　

    ISSN： 0366-7022

  141. An efficient synthesis of polymer-supported silyl linkers using a di-Grignard reagent Peer-reviewed

    Takayuki Doi, Masahito Yoshida, Ichiro Hijikuro, Takashi Takahashi

    Tetrahedron Letters　45　(29)　5723-5726　2004/07/12

    DOI： 10.1016/j.tetlet.2004.05.100 　

    ISSN： 0040-4039

  142. Selective capture of 1α,25-(OH)2-previtamin D3 utilizing polymer-supported trialkylsilyl triflate in the synthesis of 1α,25-(OH)2-vitamin D3 Peer-reviewed

    Takayuki Doi, Masahito Yoshida, Ichiro Hijikuro, Takashi Takahashi

    Tetrahedron Letters　45　(29)　5727-5729　2004/07/12

    DOI： 10.1016/j.tetlet.2004.05.125 　

    ISSN： 0040-4039

  143. Solid phase library synthesis of cyclic depsipeptides: Aurilide and aurilide analogues Peer-reviewed

    Takashi Takahashi, Hiroyuki Nagamiya, Takayuki Doi, Peter G. Griffiths, Andrew M. Bray

    Journal of Combinatorial Chemistry　5　(4)　414-428　2003/07

    DOI： 10.1021/cc020091r 　

    ISSN： 1520-4766

  144. Palladium(0)-catalyzed Mizoroki-Heck reaction and Rh(I)-catalyzed asymmetric hydrogenation of polymer-supported dehydroalanine system Peer-reviewed

    Takayuki Doi, Nobuaki Fujimoto, Jun Watanabe, Takashi Takahashi

    Tetrahedron Letters　44　(10)　2161-2165　2003/03/03

    DOI： 10.1016/S0040-4039(03)00149-7 　

    ISSN： 0040-4039

  145. Synthesis of a new troponoid liquid crystalline library on solid support Peer-reviewed

    Masashi Hashimoto, Akira Mori, Hitoshi Inoue, Hiroyuki Nagamiya, Takayuki Doi, Takashi Takahashi

    Tetrahedron Letters　44　(6)　1251-1254　2003/02/03

    DOI： 10.1016/S0040-4039(02)02813-7 　

    ISSN： 0040-4039

  146. Synthesis of a tetrabenzyl-substituted 10-membered cyclic diamide

    Takayuki Doi, Hiroyuki Nagamiya, Masaya Kokubo, Kazunori Hirabayashi, Takashi Takahashi

    Tetrahedron　58　(15)　2957-2963　2002/04/08

    DOI： 10.1016/S0040-4020(02)00204-1 　

    ISSN： 0040-4020

  147. Sequential Five-Membered Ring Formation via Intramolecular Alkene Insertion and Intramolecular Allene Insertion to a π-Allylpalladium Intermediate

    DOI Takayuki

    J. Synth. Org. Chem. Jpn.　59　(12)　38-42　2001/12/01

    Publisher: The Society of Synthetic Organic Chemistry, Japan

    DOI： 10.5059/yukigoseikyokaishi.59.1190 　

    ISSN： 0037-9980

    More details Close

    Palladium (0) -catalyzed tandem cyclization of 6-allyl-2, 7-octadienyl acetate 4 afforded the trans-fused bicyclo [3.3.0] octane 5 by intramolecular alkene insertion to a π-allylpalladium intermediate with 5-exo mode, followed by another intramolecular alkene insertion to the resulting σ-alkylpalladium intermediate. The reaction of 6, a methyl substituted derivative at the 7 position, also provided the novel trans-fused 7 and 8 whereas that of 11 which has dimethyl groups at the 2 and 7 position lead to 12 via 6-exo cyclization. Intramolecular reactions of the π-allylpalladium intermediates to allene moieties afforded two modes of cyclization (15→16 and 32→33). The former reaction was applied to a synthesis of isoiridomyrmecin (31). A domino cyclization of acyclic 41 was achieved via five and six consecutive carbon-carbon bond formations to successfully provide tricyclic 44 and tetracyclic 43.

  148. The synthesis of the CD ring of paclitaxel Peer-reviewed

    Kazuoki Nakai, Shigeru Miyamoto, Daisuke Sasuga, Takayuki Doi, Takashi Takahashi

    Tetrahedron Letters　42　(44)　7859-7862　2001/10/29

    DOI： 10.1016/S0040-4039(01)01653-7 　

    ISSN： 0040-4039

  149. Stereo- and regio-selective Ti-mediated radical cyclization of epoxy-alkenes: Synthesis of the A and C ring synthons of paclitaxel Peer-reviewed

    Kazuoki Nakai, Miyuki Kamoshita, Takayuki Doi, Haruo Yamada, Takashi Takahashi

    Tetrahedron Letters　42　(44)　7855-7857　2001/10/29

    DOI： 10.1016/S0040-4039(01)01655-0 　

    ISSN： 0040-4039

  150. Combinatorial synthesis of trisaccharides via solution-phase one-pot glycosylation Peer-reviewed

    Takashi Takahashi, Masaatsu Adachi, Akihisa Matsuda, Takayuki Doi

    Tetrahedron Letters　41　(15)　2599-2603　2000/04/08

    DOI： 10.1016/S0040-4039(00)00214-8 　

    ISSN： 0040-4039

  151. Palladium(0)-catalyzed carbonylation on the Multipin(TM) system Peer-reviewed

    Takashi Takahashi, Hitoshi Inoue, Satoshi Tomida, Takayuki Doi, Andrew M. Bray

    Tetrahedron Letters　40　(44)　7843-7846　1999/10/29

    DOI： 10.1016/S0040-4039(99)01667-6 　

    ISSN： 0040-4039

  152. New approach to the progesterone BCD-ring system by utilizing a tandem transannular radical cyclization Peer-reviewed

    Satoshi Tomida, Takayuki Doi, Takashi Takahashi

    Tetrahedron Letters　40　(12)　2363-2366　1999/03/19

    DOI： 10.1016/S0040-4039(99)00187-2 　

    ISSN： 0040-4039

  153. Glycosidation of solid-supported glycosyl donors tethered by a trialkylsilane linker Peer-reviewed

    Takayuki Doi, Masayuki Sugiki, Haruo Yamada, Takashi Takahashi, John A. Porco Jr.

    Tetrahedron Letters　40　(11)　2141-2144　1999/03/12

    Publisher: Elsevier Ltd

    DOI： 10.1016/S0040-4039(99)00133-1 　

    ISSN： 0040-4039

  154. A novel method for the stereoselective formation of trans bicyclic ketones by way of oxidative radical cyclization Peer-reviewed

    Takashi Takahashi, Satoshi Tomida, Takayuki Doi

    Synlett　(5)　644-646　1999

    Publisher: Georg Thieme Verlag

    DOI： 10.1055/s-1999-2686 　

    ISSN： 0936-5214

  155. A novel strategy for the automated synthesis of bis-amides of 1,2- diamines Peer-reviewed

    Takayuki Doi, Ichiro Hijikuro, Takashi Takahashi

    Synlett　(11)　1751-1753　1999

    Publisher: Georg Thieme Verlag

    DOI： 10.1055/s-1999-2947 　

    ISSN： 0936-5214

  156. Synthesis of 9-membered masked enediyne analogues possessing DNA intercalator and sugar moieties Peer-reviewed

    Takashi Takahashi, Hiroshi Tanaka, Akihisa Matsuda, Takayuki Doi, Haruo Yamada

    Bioorganic and Medicinal Chemistry Letters　8　(23)　3299-3302　1998/12/01

    Publisher: Elsevier Ltd

    DOI： 10.1016/S0960-894X(98)00605-2 　

    ISSN： 0960-894X

  157. DNA cleaving activities of 9-membered masked enediyne analogues possessing DNA intercalator and sugar moieties Peer-reviewed

    Takashi Takahashi, Hiroshi Tanaka, Akihisa Matsuda, Takayuki Doi, Haruo Yamada, Takuyuki Matsumoto, Daisuke Sasaki, Yukio Sugiura

    Bioorganic and Medicinal Chemistry Letters　8　(23)　3303-3306　1998/12/01

    Publisher: Elsevier Ltd

    DOI： 10.1016/S0960-894X(98)00606-4 　

    ISSN： 0960-894X

  158. Synthesis of the chiral CD rings of paclitaxel from 2-deoxy-D-ribose: Novel 1,2-addition of a dienolate to a chiral ketone

    Takashi Takahashi, Yoichiro Hirose, Hajime Iwamoto, Takayuki Doi

    Journal of Organic Chemistry　63　(17)　5742-5743　1998/08/21

    DOI： 10.1021/jo9810563 　

    ISSN： 0022-3263

  159. Solid phase approach to muscone synthesis: Rh(I)-catalyzed hydroformylation of a 1,1-disubstituted alkene on the Multipin® system Peer-reviewed

    Takashi Takahashi, Satoshi Ebata, Takayuki Doi

    Tetrahedron Letters　39　(11)　1369-1372　1998/03/12

    DOI： 10.1016/S0040-4039(97)10847-4 　

    ISSN： 0040-4039

  160. One-Pot Sequential Asymmetric Hydrogenation Utilizing Rh(I) and Ru(II) Catalysts Peer-reviewed

    Takayuki Doi, Masaya Kokubo, Keiji Yamamoto, Takashi Takahashi

    Journal of Organic Chemistry　63　(3)　428-429　1998/02/06

    Publisher: American Chemical Society

    DOI： 10.1021/jo9720400 　

    ISSN： 0022-3263

  161. Palladium(0)-catalyzed domino cyclization-carbonylation of alkenyl- allenyl-allylic acetate Peer-reviewed

    Takayuki Doi, Masaru Takasaki

    Bulletin of the Chemical Society of Japan　71　(12)　2929-2935　1998

    DOI： 10.1246/bcsj.71.2929 　

    ISSN： 0009-2673

  162. Nucleophilic substitutions on Multipin™ systems linked with a traceless linker Peer-reviewed

    Takashi Takahashi, Satoshi Tomida, Hitoshi Inoue, Takayuki Doi

    Synlett　(11)　1261-1263　1998

    Publisher: Georg Thieme Verlag

    DOI： 10.1055/s-1998-1935 　

    ISSN： 0936-5214

  163. Synthesis of Taxoid Ring Systems: AC → ABC Approach by Way of Intramolecular Alkylation Peer-reviewed

    Takashi Takahashi, Hajime Iwamoto, Kensuke Nagashima, Tadashi Okabe, Takayuki Doi

    Angewandte Chemie (International Edition in English)　36　(12)　1319-1321　1997/07/04

    Publisher: Wiley-VCH Verlag

    DOI： 10.1002/anie.199713191 　

    ISSN： 0570-0833

  164. Hydroformylation of omega-functionalized 1,1-disubstituted alkenes and its use toward the synthesis of (+/-)muscone Peer-reviewed

    T Takahashi, K Machida, Y Kido, K Nagashima, S Ebata, T Doi

    CHEMISTRY LETTERS　(12)　1291-1292　1997

    ISSN： 0366-7022

    eISSN： 1348-0715

  165. A biomimetic approach to taxol: Stereoselective synthesis of a 12-membered ring ene-epoxide

    Takashi Takahashi, Tadashi Okabe, Hajime Iwamoto, Yoichiro Hirose, Haruo Yamada, Takayuki Doi, Shuji Usui, Yoshimasa Fukazawa

    Israel Journal of Chemistry　37　(1)　31-37　1997/01/01

    Publisher: Laser Pages Publishing Ltd.

    DOI： 10.1002/ijch.199700006 　

    ISSN： 0021-2148

  166. Sequential asymmetric hydrogenation of symmetric bis-cinnamic acid derivatives: Syntheses of the C-2-symmetric core units of HIV protease inhibitors Peer-reviewed

    T Doi, K Hirabayashi, M Kokubo, T Komagata, K Yamamoto, T Takahashi

    JOURNAL OF ORGANIC CHEMISTRY　61　(24)　8360-8361　1996/11

    ISSN： 0022-3263

  167. Palladium(0)-Catalyzed Cyclization of 6-(2-Alkenyl)-2,7-octadienyl Acetates with Novel Diastereofacial Selection Peer-reviewed

    Takayuki Doi, Arata Yanagisawa, Takashi Takahashi, Keiji Yamamoto

    Synlett　1996　(2)　145-146　1996

    Publisher: Georg Thieme Verlag

    DOI： 10.1055/s-1996-5359 　

    ISSN： 0936-5214

  168. Cyanohydrin Alkylation Approach To A Chiral A-Ring Synthon For 1α,25-Dihydroxyvitamin D3 Peer-reviewed

    Takashi Takahashi, Takayuki Doi, Makoto Nakazawa, Haruo Yamada

    Natural Product Letters　1　(4)　299-304　1993/02/01

    DOI： 10.1080/10575639308050064 　

    ISSN： 1057-5634

  169. Synthesis of a Nine‐Membered Cyclic Analogue of the Neocarzinostatin Chromophore and Its DNA‐Cleaving Activity Peer-reviewed

    Takashi Takahashi, Hiroshi Tanaka, Yoshimasa Hirai, Takayuki Doi, Haruo Yamada, Takashi Shiraki, Yukio Sugiura

    Angewandte Chemie International Edition in English　32　(11)　1657-1659　1993

    DOI： 10.1002/anie.199316571 　

    ISSN： 1521-3773 0570-0833

  170. Macroring contraction methodology. 6. transannular diels-alder reaction of the 14-members (E,E,E)-trienone Peer-reviewed

    Takashi Takahashi, Yasuharu Sakamoto, Takayuki Doi

    Tetrahedron Letters　33　(24)　3519-3522　1992/06/09

    DOI： 10.1016/S0040-4039(00)92678-9 　

    ISSN： 0040-4039

  171. Syntheses and Transannular Cyclizations of Neocarzinostatin–Chromophore and Esperamicin-Calichemicin Analogues Peer-reviewed

    Takayuki Doi, Takashi Takahashi

    Journal of Organic Chemistry　56　(11)　3465-3467　1991/05/01

    DOI： 10.1021/jo00011a002 　

    ISSN： 1520-6904 0022-3263

  172. New Tool in Organic Synthesis.—Application of Computers— Peer-reviewed

    Haruo Yamada, Takayuki Doi, Takashi Takahashi

    Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry　48　(6)　593-605　1990

    DOI： 10.5059/yukigoseikyokaishi.48.593 　

    ISSN： 0037-9980

  173. Stereoselective Cyclopropanation of the 10-Membered Enone: Total Synthesis of Bicyclohumulenone Peer-reviewed

    Takashi Takahashi, Yoshiro Yamashita, Takayuki Doi, Jiro Tsuji

    Journal of Organic Chemistry　54　(18)　4273-4275　1989/09/01

    DOI： 10.1021/jo00279a008 　

    ISSN： 1520-6904 0022-3263

  174. Application of Molecular Mechanics Calculation in Natural Product Syntheses Using Macrocyclic Stereocontrolled Reactions

    TAKAHASHI Takashi, DOI Takayuki

    Journal of Japan Oil Chemists' Society　38　(5)　352-362　1989

    Publisher: Japan Oil Chemists' Society

    DOI： 10.5650/jos1956.38.352 　

    ISSN： 1884-2003

    More details Close

    Examples of the application of Molecular Mechanics (MM2) calculation in natural product syntheses using macrocyclic stereocontrolled reactions are presented. MM2 calculations and abinitio MM2 calculations have been used in predictions (or analyses) of the stereoselectivity in macrocyclic reactions such as the transannular Diels-Alder reaction of the 14-membered (E, E, E)-triene, the transannular [2, 3]-Wittig reaction of the 13-membered diallylic ethers, the cyclopropanation and the epoxidation of the 10-membered enones. Moreover molecular designing for the Bergman cyclization of the macrocyclic diynenes based on MM2 calculations are also described.

  175. Stereochemical Control in Medium and Large Membered Ring Compounds. Predictions of Stereoselectivity Based on Molecular Mechanics Calculations and Syntheses of Natural Products Peer-reviewed

    Takashi Takahashi, Takayuki Doi, Hisao Nemoto

    Journal of Synthetic Organic Chemistry, Japan　47　(2)　135-153　1989

    DOI： 10.5059/yukigoseikyokaishi.47.135 　

    ISSN： 0037-9980

Show all ︎Show first 5

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    CSJ Current Review　(36)　2020

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    増田裕一, 土井隆行

    化学工業　67　(10)　18-25　2016

    ISSN： 0451-2014

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    青木 淳賢, 可野 邦行, 濱 直人, 辻田 忠志, 土井 隆行, 菅原 明, 清水 律子, 大島 吉輝, 山本 雅之

    日本薬学会年会要旨集　135年会　(1)　155-155　2015/03

    Publisher: (公社)日本薬学会

    ISSN： 0918-9823

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    伊藤進也, 小川浩二, 竹内恒, 広川貴次, 吉田将人, 土井隆行, 五島直樹, 夏目徹, 永田和宏

    日本結合組織学会学術大会抄録集　47th　2015

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    日本細胞生物学会大会要旨集　65th　2013

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    青木 淳賢, 段 孝, 宮田 敏男, 土井 隆行, 根東 義則, 山本 雅之, 大島 吉輝

    日本薬学会年会要旨集　132年会　(1)　124-124　2012/03

    Publisher: (公社)日本薬学会

    ISSN： 0918-9823

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    大澤宏祐, 吉田将人, 高木基樹, 広川貴次, 植草義徳, 加藤晃一, 新家一男, 夏目徹, 土井隆行

    日本薬学会年会要旨集　132nd　(2)　2012

    ISSN： 0918-9823

  8. 線維化疾患治療を目指したコラーゲン特異的分子シャペロンHsp47阻害剤の探索

    伊藤進也, 伊藤進也, 小川浩二, 高木基樹, 吉田将人, 広川貴次, 新家一男, 土井隆行, 五島直樹, 夏目徹, 永田和宏

    日本生化学会大会(Web)　85th　2012

  9. 遺伝子医学MOOK21 最新ペプチド合成技術とその創薬研究への応用

    土井隆行

    遺伝子医学MOOK21　118-124　2012

    Publisher: メディカルドゥ

  10. タンパク質間相互作用阻害活性を有するThielocin B1の全合成と相互作用解析

    吉田将人, 大澤宏祐, 高木基樹, 広川貴次, 植草義徳, 加藤晃一, 新家一男, 夏目徹, 土井隆行

    天然有機化合物討論会講演要旨集　53rd　2011

  11. Total Synthesis of Apratoxin A

    DOI Takayuki, NUMAJIRI Yoshitaka, MUNAKATA Asami, TAKAHASHI Takashi

    2007　31-34　2008/03/01

    ISSN： 1344-7661

  12. Synthesis of chemical probes based on combinatorial chemistry and labo automation

    Protein, nucleic acid and enzyme　52　(13)　1655-1660　2007/10

    Publisher: 共立出版

    ISSN： 0039-9450

  13. High-throughput synthesis of combinatorial libraries based on natural products

    Takayuki Doi, Hiroshi Tanaka, Takashi Takahashi

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN　65　(8)　795-804　2007/08

    ISSN： 0037-9980

  14. コンビナトリアルケミストリーを活用した天然物とその類縁体の高速合成法の開発

    土井隆行, 田中浩士, 高橋孝志

    有機合成化学協会誌　65　(8)　795-804　2007/08

    Publisher: 有機合成化学協会

    DOI： 10.5059/yukigoseikyokaishi.65.795 　

  15. Application to combinatorial synthesis of fungal beauveriolides for drug development

    Bio industry　24　(7)　39-47　2007/07

    Publisher: シーエムシー出版

    ISSN： 0910-6545

  16. Combinatorial synthesis of natural product library

    58　(6)　459-469　2007/06

    Publisher: 化学工業社

    ISSN： 0451-2014

  17. New aureothin derivative, alloaureothin, from Streptomyces sp MM23

    Jun-ya Ueda, Junko Hashimoto, Aya Nagai, Takuji Nakashima, Hisayuki Komaki, Kozue Anzai, Shigeaki Harayama, Takayuki Doi, Takashi Takahashi, Kazuo Nagasawa, Tohru Natsume, Motoki Takagi, Kazuo Shin-ya

    JOURNAL OF ANTIBIOTICS　60　(5)　321-324　2007/05

    DOI： 10.1038/ja.2007.41 　

    ISSN： 0021-8820

  18. Synthesis of Biologically Active Fluorescence-Labeled Aerugonosin Derivatives

    Yoichiro Hoshina, Yoshifumi Yamada, Hiroshi Tanaka, Takayuki Doi, Takashi Takahash

    Bioorg. Med. Chem. Lett.　17　(10)　2904-2907　2007

    DOI： 10.1016/j.bmcl.2007.02.045 　

    ISSN： 0960-894X

  19. Donor-bound Glycosylation for Various Glycosyl Acceptors: Bidirectional Solid-phase Semisynthesis of Vancomycin and Its Derivatives.

    Takayuki Doi, Atsushi Kinbara, Hitoshi Inoue, Takashi Takahashi

    Chem. Asian J.　2　(1)　188-198　2007

    DOI： 10.1002/asia.200600301 　

    ISSN： 1861-4728

  20. Synthesis of Dimethyl Gloiosiphone A by Way of Palladium-catalyzed Domino Cyclization

    Takayuki Doi, Yusuke Iijima, Masaru Takasaki, Takashi Takahashi

    J. Org. Chem.　72　(10)　3667-3671　2007

    DOI： 10.1021/jo062546v 　

    ISSN： 0022-3263

  21. A Divergent Route to 3-Amino-2,3,6-trideoxysugars Including Branched Sugar: Synthesis of Vancosamine, Daunosamine, Saccharosamine, and Ristosamine

    Takayuki Doi, Kazuaki Shibata, Atsushi Kinbara, Takashi Takahashi

    Chem. Lett.　36　(11)　1372-1373　2007

    DOI： 10.1246/cl.2007.1372 　

    ISSN： 0366-7022 1348-0715

  22. Synthesis of the octahydroindole unit of aeruginosins via asymmetric hydrogenation of the Diels-Alder adducts of 2-amido-2,4-pentadienoate

    Yoichiro Hoshina, Takayuki Doi, Takashi Takahashi

    Tetrahedron　63　(51)　12740-12746　2007

    DOI： 10.1016/j.tet.2007.09.078 　

    ISSN： 0040-4020

  23. Absolute stereochemistry of fungal beauveriolide III and ACAT inhibitory activity of four stereoisomers (vol 71, pg 7644, 2006)

    Taichi Ohshiro, Ichiji Namatame, Kenichiro Nagai, Takafumi Sekiguchi, Takayuki Doi, Takashi Takahashi, Kazuaki Akasaka, Lawrence L. Rudel, Hiroshi Tomoda, Satoshi Omura

    JOURNAL OF ORGANIC CHEMISTRY　71　(24)　9252-9252　2006/11

    DOI： 10.1021/jo062058n 　

    ISSN： 0022-3263

    eISSN： 1520-6904

  24. コンビナトリアルケミストリーを活用した液晶化合物合成

    高橋 孝志, 土井 隆行, 吉田 将人

    未来材料　6　(6)　16-21　2006/06

    Publisher: エヌ・ティー・エス

    ISSN： 1346-0986

  25. A Total Synthesis of Apratoxin A

    Takayuki Doi, Yoshitaka Numajiri, Asami Munakata, Takashi Takahashi

    Org. Lett.　8　(3)　531-534　2006

    DOI： 10.1021/ol052907d 　

    ISSN： 1523-7060

  26. Synthesis and Biological Evaluation of a Beauveriolide Analogue Library

    Kenichiro Nagai, Takayuki Doi, Takafumi, Sekiguchi Ichiji Namatame, Toshiaki Sunazuka, Hiroshi Tomoda, Satoshi Omura, Takashi Takahashi

    J. Comb. Chem.　8　(1)　103-109　2006

    DOI： 10.1021/cc050084d 　

    ISSN： 1520-4766

  27. A formal total synthesis of taxol aided by an automated synthesizer

    Takayuki Doi, Shinichiro Fuse, Shigeru Miyamoto, Kazuoki Nakai, Daisuke Sasuga, Takashi Takahashi

    Chemistry - An Asian Journal　1　(3)　370-383　2006

    DOI： 10.1002/asia.200600156 　

    ISSN： 1861-4728 1861-471X

  28. Distinct Layered Structure with Density Modulation in Solid Phase Formed from B2 Phase of Banana Molecules

    Sungmin Kang, tokita masatoshi, Kumiko Ogino, Takayuki Doi, Takashi Takahashi, Hideo Takezoe, Junji Watanabe

    Physical Review E　73　(1)　011701(1-6)　2006

    DOI： 10.1103/PhysRevE.73.011701 　

    ISSN： 1539-3755 1550-2376

  29. Novel Regio- and Stereo-controlled Diels-Alder Reaction Tethered by Dipeptide

    DOI Takayuki, MIURA Yuko, KAWAUCHI Susumu, TAKAHASHI Takashi

    2004　141-142　2005/03/01

    ISSN： 1344-7661

  30. Synthesis of the AC Ring of Paclitaxel: Formation of the C Ring by (3+2) Cycloaddition with a Preformed A Ring

    Kazuoki Nakai, Takayuki Doi, Takashi Takahashi

    Synlett　(5)　866-868　2005

    DOI： 10.1055/s-2005-863739 　

    ISSN： 0936-5214

  31. A Library Synthesis of Pyrazoles by Azomethine Imine Cycloaddition to the Polymer-supported Vinylsulfone

    Nobuhiro Fuchi, Takayuki Doi, Takashi Takahashi

    Chem. Lett.　34　(3)　438-439　2005

    DOI： 10.1246/cl.2005.438 　

    ISSN： 0366-7022 1348-0715

  32. Combinatorial Chemistry and Its Application to the Synthesis of Liquid Crystals

    DOI Takayuki, OGINO Kumiko, TAKAHASHI Takashi

    8　(4)　235-242　2004/10/25

    Publisher: 日本液晶学会事務局

    ISSN： 1880-6449

  33. 天然物の母骨格を有する化合物ライブラリーの構築：Aeruginosin誘導体のコンビナトリアル合成

    星名洋一郎, 茂木寛幸, 土井隆行, 田中浩士, 山田純史, 長野隆, 高橋孝志

    第18回Combinatrial Chemistry研究会要旨集　34　2004

  34. LA（ラボオートメーション）導入による有機合成の効率化を指向したタキソールの全合成研究

    布施新一郎, 宮本滋, 中井一宙, 土井隆行, 高橋孝志

    第86回有機合成シンポジウム講演要旨集　80　2004

  35. π‐アリルパラジウム錯体に対する分子内アルケン挿入反応を用いたジメチルグロイオシホンAの全合成研究

    飯島悠介, 高崎優, 土井隆行, 高橋孝志

    第86回有機合成シンポジウム講演要旨集　2004

  36. Combinatorial Synthesis of Natural Products:A Library Synthesis of Macrosphelide Using Polymer-Support

    Takashi Takahashi, Shin-ichi Kusaka, Takayuki Doi, Toshiaki Sunazuka, Satoshi Omura

    IUPAC ICOS-15 Conference Program and Abstracts　392　2004

  37. Ti(III)-catalyzed radical cyclization of 6,7-epoxygeranyl acetate

    Shinichiro Fuse, Malcoln Hanochi, Takayuki Doi, Takashi Takahashi

    Tetrahedron Letters　45　(9)　1961-1963　2004

    Publisher: Elsevier Ltd

    DOI： 10.1016/j.tetlet.2003.12.138 　

    ISSN： 0040-4039

  38. High speed parallel synthesis of banana-shaped molecules and phase transition behaviour of 4-bromo-substituted derivatives

    Sungmin Kang, Jirakorn Thisayukta, hideo takezoe, Junji Watanabe, Kumiko Ogino, Takayuki Doi, Takashi Takahashi

    Liquid Crystals　31　(10)　1323-1336　2004

    DOI： 10.1080/02678290412331298094 　

    ISSN： 0267-8292

  39. A Library Synthesis of Cyclic Depsipeptides Aurilide and Its Derivatives on Solid-Support

    DOI Takayuki, NAGAMIYA Hiroyuki, TAKAHASHI Takashi

    2002　45-46　2003/02/01

    ISSN： 1344-7661

  40. 天然物の母骨格を有する化合物ライブラリーの構築 :マクロスフェライド誘導体のコンビナトリアル合成

    日下真一, 土肥卓, 土井隆行, 高橋孝志

    第45回天然有機化合物討論会講演要旨集　233-238　2003

  41. A Combinatorial Synthesis of a Macrosphelide Library Utilizing a Palladium-Catalyzed Carbonylation on a Polymer Support.

    Takashi Takahashi, Shin-ichi Kusaka, Takayuki Doi, Toshiaki Sunazuka, Satoshi Omura

    Angew. Chem. Int. Ed.　42　(42)　5230-5234　2003

    DOI： 10.1002/anie.200352229 　

    ISSN： 1433-7851

  42. Total Synthesis of Macrosphelide A by Way of Palladium-catalyzed Carbonylative Esterification.

    Shin-ichi Kusaka, Takayuki Doi, Takashi Takahashi

    Tetrahedron Lett.　44　(49)　8857-8859　2003

    Publisher: Elsevier Ltd

    DOI： 10.1016/j.tetlet.2003.09.186 　

    ISSN： 0040-4039

  43. Combinatorial chemistry in organic synthesis

    Takashi Takahashi, Takayuki Doi

    Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry　60　(5)　426-433　2002

    Publisher: Society of Synthetic Organic Chemistry

    DOI： 10.5059/yukigoseikyokaishi.60.426 　

    ISSN： 0037-9980

  44. Synthesis of the ABC Ring System of Paclitaxel: Formation of the 8-Membered Ring by Intermolecular Alkylation.

    Shigeru Miyamoto, Takayuki Doi, Takashi Takahashi

    Synlett　97-99　2002

  45. Solid-Phase Synthesis of a Phytoalexin Elicitor-Active Tetraglucosyl Glucitol

    Takashi Takahashi, Akihiro Okano, Toru Amaya, Hiroshi Tanaka, Takayuki Doi

    Synlett　911-914　2002

  46. Parallel Synthesis of a Vitamin D3 Library in the Solid-Phase .

    Ichiro Hijikuro, Takayuki Doi, Takashi Takahashi

    J. Am. Chem.Soc.　123　(16)　3716-3722　2001

    DOI： 10.1021/ja003976k 　

    ISSN： 0002-7863

  47. Synthesis of a Trisaccharide Library Using a Phenylsulfonate Traceless Linker on SynphaseTM Crowns.

    Takashi Takahashi, Hitoshi Inoue, Yuichi Yamamura, Takayuki Doi

    Angew. Chem. Int. Ed. Engl.　40　(17)　3230-3233　2001

    DOI： 10.1002/1521-3773(20010903)40:17<3230::AID-ANIE3230>3.0.CO;2-Z 　

    ISSN： 1433-7851

  48. The Synthesis of beta-Strand Mimetic Templates via Regioselective 1,3-Dipolar Cycloaddition with Vinylsulfone.

    Nobuhiro Fuchi, Takayuki Doi, Takeo, Harada Jan, Urban Bolong, Cao Michael Kahn, Takashi Takahashi

    Tetrahedron Lett.　42　(7)　1305-1308　2001

    DOI： 10.1016/S0040-4039(00)02229-2 　

    ISSN： 0040-4039

  49. Parallel Synthesis of Oligosaccharide Conjugate Enediyness onto Silyl-linked Solid-Support.

    Akihisa Matsuda, Takayuki Doi, Hiroshi Tanaka, Takashi Takahashi

    Synlett　1101-1104　2001

  50. An efficient solid-phase synthesis of the vitamin D3 system [2]

    Takayuki Doi, Ichiro Hijikuro, Takashi Takahashi

    Journal of the American Chemical Society　121　(28)　6749-6750　1999/07/21

    DOI： 10.1021/ja990739c 　

    ISSN： 0002-7863

  51. 200万種を超える化合物の立体選択的合成

    土井 隆行

    化学と工業 = Chemistry and chemical industry　52　(4)　507-507　1999/04

    ISSN： 0022-7684

  52. セリンプロテアーゼ阻害剤を指向したペプチドミメティックのデザイン・合成・ライブラリー化

    高橋孝志, 渕信寛, 土井隆行, MichaelKahn

    第9回コンビナトリアル化学研究会公開セミナー要旨集　31-33　1999

  53. コンビナトリアルケミストリーと機能性物質の合成研究

    高橋孝志, 土井隆行

    ファインケミカル　28　(18)　7-13　1999

  54. コンビナトリアルケミストリーの有機合成における新展開

    高橋孝志, 土井隆行

    現代化学　332　(56)　61-61　1998

    Publisher: 東京化学同人

    ISSN： 0386-961X

  55. Recent Progress in Syntheses of 9-Membered Masked Enediyne Analogues and their DNA Cleaving Activities

    Takashi Takahashi, Hiroshi Tanaka, Takayuki Doi, Haruo Yamada

    Journal of Synthetic Organic Chemistry, Japan　56　(11)　987-999　1998

    DOI： 10.5059/yukigoseikyokaishi.56.987 　

    ISSN： 0037-9980 1883-6526

  56. Novel Pd(0)-Catalyzed Cyclization-Carbonylation of 2-Methyl-1-vinyl-5, 6-heptadienyl Acetate : The Synthesis of(±)-Isoiridomyrmecin

    DOI Takayuki, YANAGISAWA Arata, YAMAMOTO Keiji, TAKAHASHI Takashi

    1996　(12)　1085-1086　1996/12/05

    ISSN： 0366-7022

  57. CHIRALITY TRANSFER IN PALLADIUM-CATALYZED REACTIONS OF ALLYLAMMONIUM SALTS

    T DOI, A YANAGISAWA, M MIYAZAWA, K YAMAMOTO

    TETRAHEDRON-ASYMMETRY　6　(2)　389-392　1995/02

    DOI： 10.1016/0957-4166(95)00021-G 　

    ISSN： 0957-4166

  58. Synthesis of a Nine-Membered Cyclic Analogue of the Neocarzinostatin Chromophore and Its DNA-Cleaving Activity

    Takashi Takahashi, Hiroshi Tanaka, Yoshimasa Hirai, Takayuki Doi, Haruo Yamada, Takashi Shiraki, Yukio Sugiura

    Angewante chemistry, International Edition in English　32　(11)　1657-1659　1993

    DOI： 10.1002/anie.199316571 　

    ISSN： 1433-7851

  59. Sex Pheromone Activity of Synthetic (±)-Periplanone-A and (±)-Epiperiplanone-A to Males of Periplaneta and Blatta

    TAKAHASHI Shozo, TAKEGAWA Hisashi, TAKAHASHI Takashi, DOI Takayuki

    Journal of pesticide science　13　(3)　501-503　1988

    Publisher: 日本農薬学会

    ISSN： 0385-1559

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    Sex pheromone activity of synthetic periplanone-A (PA) and its epimer (EPA) was bioassayed in six species of genera Periplaneta and Blatta. The activity of PA was about one thousandth that of periplanone-B (PB) in males of P. americana, and that of EPA was a further one thousandth lower than that of PA. PA, EPA and mixtures of PA and PB showed low pheromone activity in males of P. joponica, P. brunnea, P. australasiae and B. orientalis.

Show all ︎Show first 5

Books and Other Publications 3

  1. Middle Molecular Strategy

    Takayuki Doi

    Springer　2021

  2. Combinatorial Synthesis of Natural Product-Based Libraries

    Takayuki Doi, Takashi Takahashi

    Taylor & Francis　2006

  3. Handbook of organopalladium Chemistry for organic synthesis

    Takashi Takahashi, Takayuki Doi

    2002

Presentations 27

  1. 創薬を指向した生物活性環状ペプチド天然物の革新的合成法とその応用に関する研究 Invited

    土井隆行

    メディカル・サイエンス セミナー　2021/11/19

  2. 特異な生物活性をもつ天然物の全合成と構造決定 Invited

    土井隆行

    有機合成化学協会「2019年企業冠賞」受賞講演会　2021/01/27

  3. 環状デプシペプチド天然物の全合成、ライブラリー合成、プローブ合成、三次元構造解析 Invited

    土井隆行

    Visionary 農芸化学100 シンポジウム：天然物化学研究領域 第2回シンポジウム　2021/01/09

  4. 生物活性をもつ中分子環状ペプチドの合成と三次元構造解析 Invited

    土井 隆行

    第9回CSJ化学フェスタ2019　2019/10/17

  5. 中分子環状ペプチドの合成、生物活性、三次元構造 Invited

    土井 隆行

    日本化学会第99春季年会　2019/03/16

  6. 環状ペプチド天然物の全合成と三次元構造ー活性解析 Invited

    土井 隆行

    第393回CBI学会講演会　2018/03/20

  7. Activity Directed Total Synthesis of Natural Products and Their Analogues" Invited

    DOI Takayuki

    2017/09/16

  8. 中分子環状ペプチドの有機合成から多様な生物活性への展開 Invited

    土井 隆行

    第28回 万有仙台シンポジウム　2017/06/29

  9. 天然物を手本に：有機合成を基軸とする研究

    第50回天然物化学談話会　2015/07/01

  10. Total Synthesis of Cyclodepsipeptide Natural Products and Their Analogues International-presentation

    7th Spanish-Portuguese-Japanese Organic Chemistry Symposium　2015/06/23

  11. 生物活性環状デプシペプチド天然物の全合成，誘導体合成，活性評価，機能構造解析

    有機合成コロキウム　2014/09/20

  12. 環状デプシペプチド天然物の分子プローブ合成と結合タンパク質複合体解析

    日本プロテオーム学会2014年会　2014/07/18

  13. 生物活性環状デプシペプチド天然物の全合成，誘導体合成，活性評価、機能構造解析

    有機合成化学セミナー　2013/09/17

  14. 天然物の全合成と機能解明に向けたアプローチ

    日本薬学会第133年会　2013/03/27

  15. Total Synthesis of Apratoxin A International-presentation

    Y. Numajiri. Takahashi

    Ninth Tetrahedron Symposium　2008/07/22

  16. Synthesis and Catalytic Activity of N-Heterocyclic Carbene-Derived Pincer-Type Nickel(II) Complexes International-presentation

    Kiyofumi Inamoto, Jun-ichi Kuroda, Kou Hiroya

    17th International Conference on Organic Synthesis (ICOS-17)　2008/06/22

  17. 17th International Conference on Organic Synthesis (ICOS-17) International-presentation

    Kou Hiroya, Kei Kawamoto, Kiyofumi Inamoto

    17th International Conference on Organic Synthesis (ICOS-17)　2008/06/22

  18. Synthesis of the 9-Membered Enediyne Compound Containing a DNA Sequence Recognition Moiety International-presentation

    Yoshikazu Tanaka, Takashi Takahashi

    17th International Conference on Organic Synthesis (ICOS-17)　2008/06/22

  19. 環状ペプチド天然物の全合成と機能解明に向けたアプローチ

    特定領域研究「生体機能分子の創製」取りまとめシンポジウム　2008/06/02

  20. The 12th Japan-Korea Joint Symposium on Drug Design and Development, International-presentation

    Kou Hiroya, Kei Kawamoto, Kiyofumi Inamoto

    The 12th Japan-Korea Joint Symposium on Drug Design and Development　2008/05/14

  21. Synthesis and Catalytic Activities of Pincer-type Bis(imidazolin-2-ylidene) Nickel(II) Complexes International-presentation

    Kiyofumi Inamoto, Jun-ichi Kuroda, Kou Hiroya

    The 12th Japan-Korea Joint Symposium on Drug Design and Development　2008/05/14

  22. Synthesis of Indoles and Benzothiophenes via Palladium-Catalyzed C-H Activation International-presentation

    Kiyofumi Inamoto, Yukari Arai, Tadataka Saito, Kou Hiroya

    he 12th Japan-Korea Joint Symposium on Drug Design and Development,　2008/05/14

  23. Asymmetric Synthetic Studies of Novel Poliketide Isolated from Peperomia Duclouxii International-presentation

    Kou Hiroya, Yusuke Ichihashi, Kiyafumi Inamoto

    The 12th Japan-Korea Joint Symposium on Drug Design and Development　2008/05/14

  24. Platinum-Catalyzed Regioselective Hydration of Acetylenic Compounds International-presentation

    Kou Hiroya, Kentaro Ogiwara, Kiyofumi Inamoto

    The 12th Japan-Korea Joint Symposium on Drug Design and Development　2008/05/14

  25. Development of the Synthetic Method for the Asymmetric Quaternary Carbon Center Utilizing Desymmetric Reaction: Application to the Synthesis of (-)-Cepharamine International-presentation

    Kou Hiroya, Ryuichi Sekioka, Kouki Fuchino, Kiyofumi Inamoto

    The 12th Japan-Korea Joint Symposium on Drug Design and Development　2008/05/14

  26. 塩基選択的DNA切断を目指した9員環エンジイン誘導体の合成研究

    田中義一, 高橋孝志

    第55回有機合成化学協会関東支部シンポジウム　2008/05/09

  27. 固相合成法を用いた環状ペプチドライブラリーの合成

    第26回コンビケム研究会　2008/04/23

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Industrial Property Rights 5

  1. Cyclic peptidic compounds

    Takayuki Doi, Masahito Yoshida, Yuichi Masuda, Yuichi Onda

    Property Type: Patent

  2. 環状デプシペプチドの新規使用方法

    中尾洋一, 前島寛, 土井隆行, 山下潤, 魚崎英毅, 福島弘之

    特許6024880

    Property Type: Patent

  3. ２－ヒドロキシベンズアルデヒド化合物、これを含有するコラーゲン細胞外分泌阻害剤及び医薬品組成物

    夏目徹, 永田和宏, 伊藤進也, 土井隆行, 吉田将人

    特許6061373

    Property Type: Patent

  4. TDP1阻害活性を有する環状エノン化合物

    高橋孝志, 土井隆行, 布施新一郎, 新家一男, 高木基樹, 広川貴次, 稲葉健一, 田中正洋

    Property Type: Patent

  5. ラベル用物質とキメラ物質，これらの物質の作製方法，並びに該ラベル用物質を用いて生体物質を捕捉，構造解析又は／及び同定する方法

    新家一男, 夏目徹, 土井隆行

    4832291

    Property Type: Patent

Research Projects 9

  1. 高次細胞機能制御を可能とする非天然型アミノ酸含有環状ペプチド中分子の創製 Competitive

    土井 隆行

    Offer Organization: JSPS

    System: 科学研究費補助金新学術領域研究（中分子戦略）

    2015/04 - 2019/03

  2. アンメットな疾患領域を開拓するスマートなケモバイオ抗体 Competitive

    梅津光央

    Offer Organization: AMED

    System: 革新的バイオ医薬品創出基盤技術開発事業

    2014/10 - 2019/03

  3. 環状デプシペプチド天然物を主軸とする創薬化学基盤技術開発 Competitive

    土井 隆行

    Offer Organization: 文部科学省

    System: 科学研究費補助金基盤研究(B)

    2014/04 - 2018/03

  4. 次世代型有用天然化合物の生産技術開発 Competitive

    新家一男

    Offer Organization: 経済産業省・AMED

    System: 次世代治療・診断実現のための創薬基盤技術開発事業

    2013/04 - 2018/03

  5. ヒストン脱アセチル化酵素阻害剤の創製研究 Competitive

    土井 隆行

    Offer Organization: 文部科学省

    System: 科学研究費補助金新学術領域研究（ケモバイオ）

    2014/04 - 2015/06

  6. フロー系を用いる骨格形成反応の開発と有機合成の効率化 Competitive

    土井 隆行

    Offer Organization: 文部科学省

    System: 科学研究費補助金新学術領域研究（集積反応化学）

    2012/04 - 2014/03

  7. 生物活性天然環状デプシペプチドを基軸とするペプチドミメティスの創製 Competitive

    土井 隆行

    Offer Organization: 文部科学省

    System: 科学研究費補助金基盤研究(B)

    2011/04 - 2014/03

  8. 有用天然化合物の安定的な生産技術開発 Competitive

    新家一男

    Offer Organization: NEDO

    System: ゲノム創薬加速化支援バイオ産業基盤技術開発

    2011/04 - 2013/03

  9. フロー系を用いる骨格形成反応の開発研究 Competitive

    土井 隆行

    Offer Organization: 文部科学省

    System: 科学研究費補助金新学術領域研究（集積反応化学）

    2010/04 - 2012/03

Show all Show first 5

Social Activities 4

  1. 八戸高等学校 学部説明・模擬講義

    2016/08/30 -

    More details Close

    「薬学と創薬研究」と題して講義を行った

  2. 鶴岡南高等学校講義

    2015/09/18 -

    More details Close

    「薬学と創薬研究」と題して講義を行った

  3. 仙台第三高等学校進路講演会

    2014/05/30 -

    More details Close

    「薬学と創薬研究」と題して講義を行った

  4. 宮城県仙台第二高等学校一日大学

    2013/12/19 -

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    「分子レベルで薬をつくる」と題し、模擬授業を行なった。

Other 13

  1. 致死性疾患肺高血圧症の全く新しい病因蛋白に着目した治療薬開発

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    スクリーニングで得られたヒット化合物の構造最適化を行う。

  2. タンパク質間相互作用阻害化合物の創製

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    生体内のシグナル伝達を担うタンパク質間相互作用は，創薬ターゲットとして重要であるが，その相互作用を制御する分子の創製は難しく，創薬研究の壁となっている。なぜなら相互作用界面には酵素のように大きな活性中心周りのポケット構造はなく，タンパク質表面のでこぼこや溝による相互作用が用いられているためである。本研究では，タンパク質間相互作用部位にフィットする小分子を設計・合成し，タンパク質との結合部位を明らかにし，その三次元相互作用様式を解析することで，困難とされているタンパク質間相互作用の阻害剤開発の実例を示し，未開拓である本領域で必要とされる研究開発指針を明らかにすることを目的とする。

  3. アンメット疾患領域を開拓するスマートなケモバイオ抗体

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    抗体と生物活性化合物の連結を行う技術を開発する。

  4. 心臓再生治療に向けた新規低分子化合物の合成研究

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    ES細胞またはiPS細胞から心筋細胞への分化を促進する化合物を見出すため、既存のシクロスポリンAをベースに種々の環状ペプチド化合物を合成し、５０倍以上の活性をもつ化合物を得る。

  5. 次世代型有用天然化合物の生産技術開発

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    生合成遺伝子クラスター取得技術、および異種発現ホストによる生合成遺伝子を応用した化合物生産技術の、より高度化・高品質化、および多様化の展開を行うことによって、微生物の持つ莫大な潜在能力を引き出し、これまで人類が手にすることが困難あるいは不可能であった化合物を生産する技術、および化学修飾が困難な微生物二次代謝産物の微生物修飾酵素等を応用した微生物内誘導体展開を可能にする技術の開発を行う。

  6. 骨粗鬆症治療薬候補化合物デストラキシンEを量産する基盤技術の確立

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    「骨粗鬆症を完治できる薬」を開発するために、メタリジウム菌が生産するアミノ酸含有化合物「デストラキシンE」を量産する基盤技術の確立を目指す。申請者は、破骨細胞が備える骨溶解機能の発動がデストラキシンEによって妨げられることを見出した。デストラキシンEは、破骨細胞の発生や生存を妨げないため、骨溶解機能をピンポイントで妨げる理想的な薬になる。低分子という特徴は、経口剤として開発できるため、患者にとって朗報である。ただし、デストラキシンEの調達に要する時間とコストの面に問題がある。本申請課題では、有機合成と生合成の手法を切り口にして、デストラキシンEを量産する方法を検討する。

  7. 研究シーズ探索プログラム/タンパク質間相互作用を阻害する化合物の創製研究

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    タンパク質間相互作用を阻害する小分子化合物について、本研究ではこの化合物をもとに多置換型芳香族化合物ライブラリー構築法を開発し、コンビナトリアル合成による類縁体化合物ライブラリーを合成し、有用なシード化合物を見出す。

  8. 生合成研究用前駆体物質の合成、および新奇骨格を有する化合物の合成による構造検証

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    生合成中間体の化学合成による供給、および新奇構造を有する化合物の化学合成による構造同定を行う。

  9. 生体制御分子のインビボイメージング解析を目指した蛍光分子プローブのハイスループット合成法の開発

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    蛍光プローブを用いて個体での分子の作用を視ることにより、生きたまま作用を視ることができることから、個体をむだなく用い、様々な分子プローブを用いたイメージングが可能となる。インビボ分子生物学の発展に重要となる機能性低分子近赤外蛍光色素およびそれらを様々な分子に導入する手法の開発を目的として、新規分子プローブを設計し、コンビナトリアル合成により最適化を行うこととし次の２点について研究を進める。（１）近赤外蛍光分子のコンビナトリアル合成（２）生体制御化合物、スペーサー、および近赤外蛍光分子とのハイブリッド化技術の開発とコンビナトルアル合成

  10. Ｐ−糖タンパク質との親和性を利用した多剤体制抑制剤の開発研究

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    タキソール類似の骨格を有する化合物を合成し多剤体制抑制活性との構造活性相関をあきらかにするとともに高活性化合物を探索する。

  11. 生理活性環状デプシペプチドの合成と分子ブローブ開発

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    生理活性天然環状デプシペプチド化合物のコンビナトリアル合成による構造活性相関の研究と分子プローブ合成

  12. 生理活性天然物環状デプシペプチドを基にしたペプチドミメティクスの創製

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    計算化学に基づく分子設計とコンビナトリアル合成による化合物ライブラリーの構築を基盤としてボーベリオライドIIIの活性三次元構造を明らかにし，その構造情報をもとにペプチドミメティックスを設計・合成する。

  13. 化合物等の高機能化技術開発

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    「スクリーニング技術開発（天然化合物）」にて得られた化合物情報とテーマ③「タンパク質相互作用予測」で得られたin silico情報を活用して、高活性が見込まれている天然物を母骨格として、コンビナトリアル合成を行うため活性部分構造ユニットに分割し，それらの合成法を確立する。単純作業となるユニットの合成についての数工程を自動化し、人の作業の軽減と大規模合成の実現を図る。

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