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Masaatsu Adachi

Section

Graduate School of Pharmaceutical Sciences

Job title

Associate Professor

Degree

博士（工学）（東京工業大学）
修士（工学）（東京工業大学）

researchmap

https://researchmap.jp/read0139539

J-GLOBAL ID

200901005651330203

Research History 9

2018/04/01 - Present

Nagoya University　Graduate School of Bioagricultural Sciences　Lecturer
2017/05/01 - 2018/03/31

Nagoya University　Graduate School of Bioagricultural Sciences Department of Applied Molecular Biosciences Division of Biofunctional Chemistry　Lecturer
2007/04/01 - 2017/04/30

Nagoya University　Graduate School of Bioagricultural Sciences Department of Applied Molecular Biosciences　Assistant Professor
2006/04/01 - 2007/03/31

Nagoya University　Graduate School of Bioagricultural Sciences Department of Applied Molecular Biosciences　Assistant
2006/04 - 2007/03

Nagoya University　Graduate School of Bioagricultural Sciences
2004/10 - 2006/03

米国Harvard大学博士研究員
2004/04 - 2004/09

財団法人理工学振興会博士研究員
2007/04 -

Nagoya University　Graduate School of Bioagricultural Sciences
Nagoya University Graduate School of Bioagricultural Sciences　Lecturer

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Professional Memberships 1

日本化学会、日本農芸化学会、日本糖質学会、有機合成化学協会

Research Interests 1

有機合成化学生物有機化学天然物有機化学

Research Areas 1

Life sciences / Pharmaceuticals - chemistry and drug development /

Awards 2

糖鎖科学名古屋拠点若手研究者奨励賞

2010　糖鎖科学名古屋拠点
２００６年度（第１９回）有機合成化学協会研究企画賞

2007/02

Papers 51

The odor of a nontoxic tetrodotoxin analog, 5,6,11-trideoxytetrodotoxin, is detected by specific olfactory sensory neurons of the green spotted puffers but is processed in overlapping olfactory bulbar area with food odors

Takehisa Suzuki, Ryota Nakahigashi, Masaatsu Adachi, Toshio Nishikawa, Hideki Abe

bioRxiv　2023/08/22

DOI： 10.1101/2023.08.22.552781 　
An almost nontoxic tetrodotoxin analog, 5,6,11-trideoxytetrodotoxin, as an odorant for the grass puffer. International-journal Peer-reviewed

Yoshihisa Noguchi, Takehisa Suzuki, Keigo Matsutani, Ryo Sakakibara, Ryota Nakahigashi, Masaatsu Adachi, Toshio Nishikawa, Hideki Abe

Scientific reports　12　(1)　15087-15087　2022/09/05

DOI： 10.1038/s41598-022-19355-6 　

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Toxic puffers contain the potent neurotoxin, tetrodotoxin (TTX). Although TTX is considered to serve as a defense substance, previous behavioral studies have demonstrated that TTX acts as an attractive pheromone for some toxic puffers. To elucidate the physiological mechanism of putative pheromonal action of TTX, we examined whether grass puffers Takifugu alboplumbeus can detect TTX. Electroolfactogram (EOG) results suggest that the olfactory epithelium (OE) of grass puffers responded to a type of TTX analog (5,6,11-trideoxyTTX), although it did not respond to TTX. We also examined the attractive action of 5,6,11-trideoxyTTX on grass puffers by recording their swimming behavior under dark conditions. Grass puffers preferred to stay on the side of the aquarium where 5,6,11-trideoxyTTX was administered, and their swimming speed decreased. Additionally, odorant-induced labeling of olfactory sensory neurons by immunohistochemistry against neural activity marker (phosphorylated extracellular signal regulated kinase; pERK) revealed that labeled olfactory sensory neurons were localized in the region surrounding "islets" where there was considered as nonsensory epithelium. 5,6,11-trideoxyTTX has been known to accumulate in grass puffers, but its toxicity is much lower (almost nontoxic) than TTX. Our results suggest that toxic puffers may positively use this TTX analog, which has been present in their body with TTX but whose function was unknown, as an odorant for chemical communication or effective TTX accumulation.
Total Syntheses of the Proposed Biosynthetic Intermediates of Tetrodotoxin Tb-210B, Tb-226, Tb-242C, and Tb-258. International-journal

Masafumi Nishiumi, Tadachika Miyasaka, Masaatsu Adachi, Toshio Nishikawa

The Journal of organic chemistry　87　(14)　9023-9033　2022/07/15

DOI： 10.1021/acs.joc.2c00704 　

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The collective synthesis of the four spiro-cyclic guanidines Tb-210B, Tb-226, Tb-242C, and Tb-258, all of which have been isolated from puffer fish and are considered possible biosynthetic intermediates of tetrodotoxin, has been achieved. Our synthesis is based on the stepwise deoxygenation or hydroxylation of a common intermediate, prepared from a known oxazoline.
Domestic cat damage to plant leaves containing iridoids enhances chemical repellency to pests

Reiko Uenoyama, Tamako Miyazaki, Masaatsu Adachi, Toshio Nishikawa, Jane L. Hurst, Masao Miyazaki

iScience　25　(7)　2022/07/15

DOI： 10.1016/j.isci.2022.104455 　

eISSN： 2589-0042
Domestic cat damage to plant leaves containing iridoids enhances chemical repellency to pests. International-journal

Reiko Uenoyama, Tamako Miyazaki, Masaatsu Adachi, Toshio Nishikawa, Jane L Hurst, Masao Miyazaki

iScience　25　(7)　104455-104455　2022/07/15

DOI： 10.1016/j.isci.2022.104455 　

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Catnip (Nepeta cataria) and silver vine (Actinidia polygama) produce iridoids with arthropod-repellent effects. Cats rub and roll against these plants, transferring iridoids to their fur that repels mosquitoes. Cats also lick and chew plant leaves during this response, although the benefit of this additional behavior has remained unknown. Here, we show that feline leaf damage substantially increases iridoid emission from both plants while also diversifying iridoids in silver vine. Cats show an equivalent duration of response to the complex cocktail of iridoids in damaged silver vine and to the much higher level of a single iridoid produced by damaged catnip. The more complex iridoid cocktail produced when silver vine is licked and chewed by cats increases mosquito repellency at low concentration. In conclusion, feline leaf damage contributes by releasing more mosquito-repellent iridoids. Feline olfactory and behavioral sensitivity is fine-tuned to plant-specific iridoid production for maximizing the mosquito repellency gained.
Synthesis of the 8-Deoxy Analogue of 4,9-Anhydro-10-hemiketal-5-deoxy-tetrodotoxin, a Proposed Biosynthetic Precursor of Tetrodotoxin. International-journal Peer-reviewed

Tadachika Miyasaka, Masaatsu Adachi, Toshio Nishikawa

Organic letters　23　(23)　9232-9236　2021/12/03

DOI： 10.1021/acs.orglett.1c03565 　

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Despite decades of research, the biosynthesis of tetrodotoxin, also known as a puffer fish toxin, remains an unsolved mystery. We disclose a synthesis of the 8-deoxy analogue of 4,9-anhydro-10-hemiketal-5-deoxy-tetrodotoxin, a possible biosynthetic precursor of tetrodotoxin isolated from the Japanese toxic newt, by an intramolecular radical cyclization of a known starting material.
JBIR-155, a Specific Class D β-Lactamase Inhibitor of Microbial Origin. International-journal Peer-reviewed

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.
First Detection of Tetrodotoxins in the Cotylean Flatworm Prosthiostomum trilineatum. International-journal Peer-reviewed

Rei Suo, Maho Kashitani, Hikaru Oyama, Masaatsu Adachi, Ryota Nakahigashi, Ryo Sakakibara, Toshio Nishikawa, Haruo Sugita, Shiro Itoi

Marine drugs　19　(1)　2021/01/18

DOI： 10.3390/md19010040 　

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Several polyclad flatworm species are known to contain high levels of tetrodotoxin (TTX), but currently TTX-bearing flatworms seem to be restricted to specific Planocera lineages belonging to the suborder Acotylea. During our ongoing study of flatworm toxins, high concentrations of TTXs were detected for the first time in the flatworm Prosthiostomum trilineatum, suborder Cotylea, from the coastal area of Hayama, Kanagawa, Japan. Toxin levels were investigated by high performance liquid chromatography-tandem mass spectrometry (LC-MS/MS), revealing that this species contains comparable concentrations of toxins as seen in planocerid flatworms such as Planocera multitentaculata. This finding indicated that there may be other species with significant levels of TTXs. The distribution of TTXs among other flatworm species is thus of great interest.
The characteristic response of domestic cats to plant iridoids allows them to gain chemical defense against mosquitoes. International-journal Peer-reviewed

Reiko Uenoyama, Tamako Miyazaki, Jane L Hurst, Robert J Beynon, Masaatsu Adachi, Takanobu Murooka, Ibuki Onoda, Yu Miyazawa, Rieko Katayama, Tetsuro Yamashita, Shuji Kaneko, Toshio Nishikawa, Masao Miyazaki

Science advances　7　(4)　2021/01

DOI： 10.1126/sciadv.abd9135 　

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Domestic cats and other felids rub their faces and heads against catnip (Nepeta cataria) and silver vine (Actinidia polygama) and roll on the ground as a characteristic response. While this response is well known, its biological function and underlying mechanism remain undetermined. Here, we uncover the neurophysiological mechanism and functional outcome of this feline response. We found that the iridoid nepetalactol is the major component of silver vine that elicits this potent response in cats and other felids. Nepetalactol increased plasma β-endorphin levels in cats, while pharmacological inhibition of μ-opioid receptors suppressed the classic rubbing response. Rubbing behavior transfers nepetalactol onto the faces and heads of respondents where it repels the mosquito, Aedes albopictus Thus, self-anointing behavior helps to protect cats against mosquito bites. The characteristic response of cats to nepetalactol via the μ-opioid system provides an important example of chemical pest defense using plant metabolites in nonhuman mammals.
Biosynthesis of Indole Diterpene Lolitrems: Radical‐Induced Cyclization of an Epoxyalcohol Affording a Characteristic Lolitremane Skeleton Peer-reviewed

Yulu Jiang, Taro Ozaki, Mei Harada, Tadachika Miyasaka, Hajime Sato, Kazunori Miyamoto, Junichiro Kanazawa, Chengwei Liu, Jun‐ichi Maruyama, Masaatsu Adachi, Atsuo Nakazaki, Toshio Nishikawa, Masanobu Uchiyama, Atsushi Minami, Hideaki Oikawa

Angewandte Chemie　132　(41)　18152-18158　2020/10/05
Publisher: Wiley
DOI： 10.1002/ange.202007280 　

ISSN： 0044-8249

eISSN： 1521-3757
Biosynthesis of Indole Diterpene Lolitrems: Radical-Induced Cyclization of an Epoxyalcohol Affording a Characteristic Lolitremane Skeleton. International-journal Peer-reviewed

Yulu Jiang, Taro Ozaki, Mei Harada, Tadachika Miyasaka, Hajime Sato, Kazunori Miyamoto, Junichiro Kanazawa, Chengwei Liu, Jun-Ichi Maruyama, Masaatsu Adachi, Atsuo Nakazaki, Toshio Nishikawa, Masanobu Uchiyama, Atsushi Minami, Hideaki Oikawa

Angewandte Chemie (International ed. in English)　59　(41)　17996-18002　2020/10/05

DOI： 10.1002/anie.202007280 　

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Lolitrems are tremorgenic indole diterpenes that exhibit a unique 5/6 bicyclic system of the indole moiety. Although genetic analysis has indicated that the prenyltransferase LtmE and the cytochrome P450 LtmJ are involved in the construction of this unique structure, the detailed mechanism remains to be elucidated. Herein, we report the reconstitution of the biosynthetic pathway for lolitrems employing a recently established genome-editing technique for the expression host Aspergillus oryzae. Heterologous expression and bioconversion of the various intermediates revealed that LtmJ catalyzes multistep oxidation to furnish the lolitrem core. We also isolated the key reaction intermediate with an epoxyalcohol moiety. This observation allowed us to establish the mechanism of radical-induced cyclization, which was firmly supported by density functional theory calculations and a model experiment with a synthetic analogue.
Asymmetric Synthesis of the Aromatic Fragment of Sespendole. Peer-reviewed

Yoshiki Ono, Atsuo Nakazaki, kaori Ueki, Keiko Higuchi, Uraiwan Sriphana, Masaatsu Adachi, Toshio Nishikawa

J. Org. Chem.　84　9750-9757　2019/10
A Concise Stereocontrolled Synthesis of an α-Carbagalactose Segment of RCAI-56, a Candidate of Anticancer Agent. Peer-reviewed

Naoki Ushida, Nobukazu Nagai, Masaatsu Adachi, Toshio Nishikawa

Synlett　977-981　2019/06
Total Syntheses and Determination of Absolute Configurations of Cep-212 and Cep-210, Predicted Biosynthetic Intermediates of Tetrodotoxin Isolated from Toxic Newt. Peer-reviewed

Masaatsu Adachi, Tadachika Miyasaka, Yuta Kudo, keita Sugimoto, Mari Yotsu-Yamashita, Toshio Nishikawa

Org. Lett.　21　(3)　780-784　2019/05
Publisher: American Chemical Society (ACS)
DOI： 10.1021/acs.orglett.8b04043 　

ISSN： 1523-7060

eISSN： 1523-7052
Facile Enzymatic Synthesis of Phosphatidylthreonine Using an Engineered Phospholipase D

Jasmina Damnjanović, Nozomi Matsunaga, Masaatsu Adachi, Hideo Nakano, Yugo Iwasaki

European Journal of Lipid Science and Technology　120　(6)　2018/06/01
Publisher: Wiley-VCH Verlag
DOI： 10.1002/ejlt.201800089 　

ISSN： 1438-9312 1438-7697
Differential binding of tetrodotoxin and its derivatives to voltage-sensitive sodium channel subtypes (Na(v)1.1 to Na(v)1.7)

Tadaaki Tsukamoto, Yukie Chiba, Minoru Wakamori, Tomoshi Yamada, Shunsuke Tsunogae, Yuko Cho, Ryo Sakakibara, Takuya Imazu, Shouta Tokoro, Yoshiki Satake, Masaatsu Adachi, Toshio Nishikawa, Mari Yotsu-Yamashita, Keiichi Konoki

BRITISH JOURNAL OF PHARMACOLOGY　174　(21)　3881-3892　2017/11

DOI： 10.1111/bph.13985 　

ISSN： 0007-1188

eISSN： 1476-5381
One-Step Transformation of Trichloroacetamide into Isonitrile Peer-reviewed

Masaatsu Adachi, Tadachika Miyasaka, Honoka Hashimoto, Toshio Nishikawa

ORGANIC LETTERS　19　(2)　380-383　2017/01

DOI： 10.1021/acs.orglett.6b03583 　

ISSN： 1523-7060

eISSN： 1523-7052
Direct Enzymatic Synthesis of 1-Phosphatidyl-β-D-glucose by Engineered Phospholipase D Peer-reviewed

Arisa Inoue, Masaatsu Adachi, Jasmina Damnjanović, Hideo Nakano, Yugo Iwasaki

ChemistrySelect　1　(13)　4121-4125　2016
Publisher: Wiley-Blackwell
DOI： 10.1002/slct.201600839 　

ISSN： 2365-6549
Improved Syntheses of (+)-Iridomyrmecin and (-)-Isoiridomyrmecin, Major Components of Matatabilactone. Peer-reviewed

Masaatsu Adachi, Yu Miyazawa, Toshio Nishikawa

Natural Product Communications　11　883-886　2016/01
Multifunctionality of the N-Trichloroacetyl Group Developed in the Synthesis of Tetrodotoxin, a Puffer Fish Toxin. Invited Peer-reviewed

Nishikawa, T, Urabe, D, Adachi, M, Isobe, M

Synlett　26　1930-1939　2015/07/01
分子内C-グリコシル化反応を利用したPolygalolide Aの全合成 Invited Peer-reviewed

安立昌篤

有機合成化学協会誌　73　607-615　2015/05/01
Asymmetric synthesis of 3-azide-4-fluoro-l-phenylalanine Peer-reviewed

Masaatsu Adachi, Mado Nakajima, Minoru Isobe

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY　79　(5)　707-709　2015/05

DOI： 10.1080/09168451.2014.997185 　

ISSN： 0916-8451

eISSN： 1347-6947
Stereocontrolled Synthesis of ABC Tricycle of Solanoeclepin A Peer-reviewed

Masaatsu Adachi, Mai Torii, Toshio Nishikawa

SYNLETT　26　(7)　965-969　2015/04

DOI： 10.1055/s-0034-1380399 　

ISSN： 0936-5214

eISSN： 1437-2096
A New Deprotection Procedure of MTM Ether Peer-reviewed

Adachi, M, Hashimoto, H, Sakakibara, R, Imazu, T, Nishikawa, T

Synlett　2498-2502　2014/12/01
Synthesis of 5,6,11-Trideoxytetrodotoxin Peer-reviewed

Masaatsu Adachi, Ryo Sakakibara, Yoshiki Satake, Minoru Isobe, Toshio Nishikawa

CHEMISTRY LETTERS　43　(11)　1719-1721　2014/11

DOI： 10.1246/cl.140684 　

ISSN： 0366-7022

eISSN： 1348-0715
Synthesis of 5- and 8-deoxytetrodotoxin Peer-reviewed

Yoshiki Satake, Masaatsu Adachi, Shouta Tokoro, Mari Yotsu-Yamashita, Minoru Isobe, Toshio Nishikawa

Chemistry - An Asian Journal　9　(7)　1922-1932　2014
Publisher: John Wiley and Sons Ltd
DOI： 10.1002/asia.201402202 　

ISSN： 1861-471X 1861-4728
Total Synthesis of Chiriquitoxin, an Analogue of Tetrodotoxin Isolated from the Skin of a Dart Frog Peer-reviewed

Masaatsu Adachi, Takuya Imazu, Ryo Sakakibara, Yoshiki Satake, Minoru Isobe, Toshio Nishikawa

CHEMISTRY-A EUROPEAN JOURNAL　20　(5)　1247-1251　2014/01

DOI： 10.1002/chem.201304110 　

ISSN： 0947-6539

eISSN： 1521-3765
First Identification of 5,11-Dideoxytetrodotoxin in Marine Animals, and Characterization of Major Fragment Ions of Tetrodotoxin and Its Analogs by High Resolution ESI-MS/MS Peer-reviewed

Mari Yotsu-Yamashita, Yuka Abe, Yuta Kudo, Raphael Ritson-Williams, Valerie J. Paul, Keiichi Konoki, Yuko Cho, Masaatsu Adachi, Takuya Imazu, Toshio Nishikawa, Minoru Isobe

MARINE DRUGS　11　(8)　2799-2813　2013/08

DOI： 10.3390/md11082799 　

ISSN： 1660-3397
Stereocontrolled Total Synthesis of Polygalolide A. Peer-reviewed

Yamada, H, Adachi, M, Isobe, M, Nishikawa, T

Chem. Asian. J.　8　1428-1435　2013/04

DOI： 10.1002/asia.201300362. 　
An Improved Synthesis of (-)-5,11-Dideoxytetrodotoxin Peer-reviewed

Masaatsu Adachi, Takuya Imazu, Minoru Isobe, Toshio Nishikawa

JOURNAL OF ORGANIC CHEMISTRY　78　(4)　1699-1705　2013/02

DOI： 10.1021/jo302773f 　

ISSN： 0022-3263
Stereocontrolled synthesis of the oxathiabicyclo[3.3.1] nonane core structure of tagetitoxin Peer-reviewed

Hitomi Yamada, Masaatsu Adachi, Toshio Nishikawa

CHEMICAL COMMUNICATIONS　49　(95)　11221-11223　2013

DOI： 10.1039/c3cc46949b 　

ISSN： 1359-7345

eISSN： 1364-548X
A Concise Synthesis of a Highly Strained Cyclobutane in Solanoeclepin A by Radical Cyclization Peer-reviewed

Takema Komada, Masaatsu Adachi, Toshio Nishikawa

CHEMISTRY LETTERS　41　(3)　287-289　2012/03

DOI： 10.1246/cl.2012.287 　

ISSN： 0366-7022

eISSN： 1348-0715
Stereocontrolled Synthesis of an Indole Moiety of Sespendole and Stereochemical Assignment of the Side Chain Peer-reviewed

Masaatsu Adachi, Keiko Higuchi, Nopporn Thasana, Hitomi Yamada, Toshio Nishikawa

ORGANIC LETTERS　14　(1)　114-117　2012/01

DOI： 10.1021/ol202895u 　

ISSN： 1523-7060
Total Synthesis of Polygalolide A Peer-reviewed

Masaatsu Adachi, Hitomi Yamada, Minoru Isobe, Toshio Nishikawa

Org. Lett.　10.1021/ol2028256　2011/11/18
A New Ring Expansion for a Chiral Hexahydroazulene Skeleton Possessing an Angular Methyl Group Peer-reviewed

Masaatsu Adachi, Takema Komada, Toshio Nishikawa

J. Org. Chem.　(76)　6942-6945　2011/07/01
Synthetic Study on Polygalolides by Intramolecular C-Glycosylation

Yamada Hitomi, Adachi Masaatsu, Isobe Minoru, Nishikawa Toshio

Symposium on the Chemistry of Natural Products, symposium papers　(52)　103-108　2010/09/01
Publisher: Symposium on the chemistry of natural products
DOI： 10.24496/tennenyuki.52.0_103 　

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Polygalolide A and B (Figure 1) were isolated from a Chinese medicinal plant, Polygala fallax, by Wei and co-workers in 2003. These structures indlude an oxabicyclo[3.2.1]ocate, a five-membered lactone, s six membered ether, an aromatic ring and contiguous quaternary stereo centers at the C-2 and C-8 positions. Total synthesis was reported by Hashimoto in 2006 and Snider in 2007. Although details of the biological activity have not been reported yet, polygalolides are attractive target for tatal synthesis because of the novel structure. In order to construct the congiguous quaternary stereo centers, the core structure of polygalolides, we have developed a new synthetic methodology through intramolecular C-glycocylation; siloxyfuran 4 underwent cyclization upon treatment of TiCl_4 or BF_3・OEt_2 to give the desired oxabicyclo compounds 5-A and 5-B (Table 1). Based on the above results, siloxyfuran 11 including acetylene at the C-8 position was synthesized from D-glucal in 13 steps. Treatment of 11 with TiCl_4 or BF_3・OEt_2 gave a byproduct 13 instead of a disired product 12. Further investigations led us to find that reaction of 11 with Et_3N and TBSOTf in CH_2Cl_2 afforded an oxabicyclo compound 12 as a single diasereomer in 63% yield. Reduction of unsaturated lactone of 12 was followed by radical deoxygenation at the C-3 position via xanthate 16 and then destannylation to give olefin 18. Deprotection of benzyl group, followed by oxidation gave enone 19. Further investigation toward the total synthesis of polygalolides is now in progress.
Synthesis of an Advanced Intermediate Bearing Two Hydroxy Groups for (-)-Tetrodotoxin and Its Analogs Peer-reviewed

Toshio Nishikawa, Yuya Koide, Masaatsu Adachi, Minoru Isobe

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN　83　(1)　66-68　2010/01

DOI： 10.1246/bcsj.20090223 　

ISSN： 0009-2673

eISSN： 1348-0634
Novel Stereocontrolled Synthesis of Highly Functionalized Cyclobutanes by Epoxide Opening through a Carbanion Intermediate in Heteroconjugate Addition Peer-reviewed

Masaatsu Adachi, Eiji Yamauchi, Takema Komada, Minoru Isobe

SYNLETT　(7)　1157-1161　2009/04

DOI： 10.1055/s-0028-1088108 　

ISSN： 0936-5214
Streptomyces phospholipase D mutants with altered substrate specificity capable of phosphatidylinositol synthesis Peer-reviewed

Atsushi Masayama, Tetsuya Takahashi, Kaori Tsukada, Seigo Nishikawa, Rie Takahashi, Masaatsu Adach, Kazushi Koga, Atsuo Suzuki, Takashi Yamane, Hideo Nakano, Yugo Iwasaki

CHEMBIOCHEM　9　(6)　974-981　2008/04

DOI： 10.1002/cbic.200700528 　

ISSN： 1439-4227

eISSN： 1439-7633
N-Heterocyclic Carbenes Catalyzed Umpolung Reactions via Homoenolates. Peer-reviewed

Masaatsu Adachi

Journal of Synthetic Organic Chemistry　65　1009-1010　2007
Degradation and reconstruction of moenomycin A and derivatives: Dissecting the function of the isoprenoid chain Peer-reviewed

Masaatsu Adachi, Yi Zhang, Catherine Leimkuhler, Binyuan Sun, John V. LaTour, Daniel E. Kahne

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY　128　(43)　14012-14013　2006/11

DOI： 10.1021/ja065905c 　

ISSN： 0002-7863
Synthetic study of alpha(2,8) oligosialoside using N-Troc sialyl N-phenyltrifluoroimidate Peer-reviewed

H Tanaka, Y Nishiura, M Adachi, T Takahashi

HETEROCYCLES　67　(1)　107-112　2006/01

ISSN： 0385-5414
Efficient Stereoselective Synthesis of γ-N-Glycosyl Asparagines by N-Glycosylation of Primary Amide Groups. Peer-reviewed

Hiroshi Tanaka, Yuki Iwata, Daisuke Takahashi, Masaatsu Adachi, Takashi Takahashi

J. Am. Chem. Soc.　127, 1630-1631　2005
One-pot Synthesis of Sialo-containing Glycosyl Amino Acids by Use of an N-Trichloroethoxycarbonyl-β-thiophenyl Sialoside. Peer-reviewed

Hiroshi Tanaka, Masaatsu Adachi, Takashi Takahashi

Chem. Eur. J.　11, 849-862　2005
31(D-1) The High-Speed Synthesis of Biologically Active Oligosaccharides (Dimeric Lewis X and Sialo-Containing Glycosyl Amino Acids) by One-Pot Clycosylation

Tanaka Hiroshi, Matoba Nobuatsu, Adachi Masaatsu, Tsukamoto Hirokazu, Takahashi Takashi

Symposium on the Chemistry of Natural Products, symposium papers　(46)　161-166　2004/10/01
Publisher: Symposium on the chemistry of natural products
DOI： 10.24496/tennenyuki.46.0_161 　

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Oligosaccharides on cell surface play important roles in many biological processes. Most biologically active oligosaccharides are rare, and are difficult to be purified. Additionally, their structural diversity based upon stereo- and regio-isomers makes it difficult to not only determine their structures, but also to accomplish its chemical synthesis in comparison with those of oligopeptides and oligonucleotides. We have investigated the one-pot glycosylation based on the chemoselective activation of glycosyl donors attached with different leaving groups with appropriate activators. Herein we report the high-speed synthesis of biologically active oligosaccharides (dimeric Lewis X and sialo-containing glycosyl amino acids) by one-pot glycosylation. In the first topic, we descried the synthesis of a protected dimeric Lewis X epitope by sequential one-pot glycosylation and an application to the automated synthesis of a protected dimeric Lewis X library. We designed sequential one-pot four-step glycosylations to provide octasaccharide 12 from five different building blocks 2 and 4-7. One-pot glycosylation using 2-5 provided the glycosyl fluoride 3 in good yield. The following one-pot glycosylation involving glycosylation of 2 with the glycosyl fluoride 3 and coupling with additional two building blocks 4 and 5 afforded a protected octasaccharide 12 in excellent yield. The synthesis of 12 member hepta-to di-saccharides 13 and 14 was accomplished by the one-pot glycosylation utilizing an solution-phase automated synthesizer. In the next topic, we report one-pot glycosylation involving sialylation to provide sialo-containing glycosyl amino acids 19 and 20. We first examined glycosidation of thiosialoside varying the protecting group at the C5 amino group. N-Troc thiosialoside 21 was found to be effective for sialylation. Using the sialyl donor 21, linear and branched type one-pot glycosylations were accomplished to provide linear and branched trisaccharides 27 and 31 in excellent yields with good stereoselectivity at the anomeric position.
An effective sialylation method using N-Troc- and N-Fmoc-protected beta-thiophenyl sialosides and application to the one-pot two-step synthesis of 2,6-sialyl-T antigen Peer-reviewed

M Adachi, H Tanaka, T Takahashi

SYNLETT　(4)　609-614　2004/03

DOI： 10.1055/s-2004-817759 　

ISSN： 0936-5214
Efficient Synthesis of Core 2 Class Glycosyl Amino Acids by One-pot Glycosylation Approach. Peer-reviewed

Hiroshi Tanaka, Masaatsu Adachi, Takashi Takahashi

Tetrahedron Lett.　45, 1433-1436　2004
Synthesis of di-branched heptasaccharide by one-pot glycosylation using seven independent building blocks Peer-reviewed

Hiroshi Tanaka, Masaatsu Adachi, Hirokazu Tsukamoto, Takeji Ikeda, Haruo Yamada, Takashi Takahashi

Organic Letters　4　(24)　4213-4216　2002/11/28

DOI： 10.1021/ol020150+ 　

ISSN： 1523-7060
Efficient Synthesis of Core 2 Class Glycosyl Amino Acids by One-pot Glycosylation Approach. Peer-reviewed

Hiroshi Tanaka, Masaatsu Adachi, Hirokazu Tsukamoto, Takeji Ikeda, Haruo Yamada, Takashi Takahashi

Org. Lett.　4, 4213-4216.　2002
21 Synthetic Study of Oligosaccharide Library Toward Automation : Combinatorial Synthesis and Structure-Activity Relationship of Oligosaccharides Having Phytoalexin Elicitor Activity

Takahashi Takashi, Amaya Toru, Adachi Masaatsu, Ikeda Takeji, Tsukamoto Hirokazu, Tanaka Hiroshi

Symposium on the Chemistry of Natural Products, symposium papers　(42)　121-126　2000/10/01
Publisher: Symposium on the chemistry of natural products
DOI： 10.24496/tennenyuki.42.0_121 　

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Oligosaccharides play a lot of important roles in biological processes and in pathology. While the automated synthesis of peptides and oligonucleotides was established decades ago, there have not been a general method for the synthesis of complex oligosaccharides. Recently the development of a broadly applicable synthetic strategy has been desired in this field. Here we wish to report the two efficient and practical strategies based on a one-pot sequential glycosidation and selective deprotection followed by glycosylation toward the automated synthesis of a oligosaccharide library. In the synthesis of heptasaccharide 3 having elicitor activity in soybean, we achieved a onepot 6-step glycosidation using a combination of different leaving groups, i.e., bromide (-Br), ethylthio group (-SEt), phenylthio group (-SPh), and fluoride (-F), with selective activators, AgOTf, MeOTf, DMTST, and HfCp_2(OTf)_2, respectively and differences of the reactivity of hydroxy groups of glycosyl acceptors. This method was applied to synthesize a library of tetra-, penta-, heptasaccharides using a manual synthesizer. For a study of the structure-activity relationship of elicitor active oligosaccharide in rice cell we demonstrated the synthesis of the oligosaccharide library having β(1→6) linkage at the various positions on β(1→3) tetrasaccharide backborn. Selective deprotection of three protecting groups (AOC, Lev, and Fmoc) of tetrasaccharide 4 was sequentially achieved to afford respective three mono-ols, three diols, and one triol, independently. Glycosylation of all glycosyl acceptors provided the corresponding oligosaccharides, respectively. These procedures were achieved on an automated synthesizer and by parallel column chromatography.
Combinatorial synthesis of trisaccharides via solution-phase one-pot glycosylation Peer-reviewed

T Takahashi, M Adachi, A Matsuda, T Doi

TETRAHEDRON LETTERS　41　(15)　2599-2603　2000/04

ISSN： 0040-4039

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Misc. 46

Synthetic studies on 4,9-anhydro-10-hemiketal-5-deoxytetrodotoxin

宮坂忠親, 安立昌篤, 西川俊夫

日本農芸化学会大会講演要旨集(Web)　2021　2021

ISSN： 2186-7976
テトロドトキシン推定生合成中間体のテトロドトキシン含有生物への投与

杉本敬太, 工藤雄大, 宮坂忠親, 安立昌篤, 長由扶子, 此木敬一, 千葉親文, 西川俊夫, 山下まり

日本農芸化学会大会講演要旨集(Web)　2019　2019

ISSN： 2186-7976
テトロドトキシンの推定生合成中間体の全合成と絶対立体配置の決定

宮坂忠親, 安立昌篤, 工藤雄大, 杉本敬太, 山下まり, 西川俊夫

日本農芸化学会大会講演要旨集(Web)　2019　2019

ISSN： 2186-7976
多環テルペンインドールの新合成法

山口将司, 小野義貴, 樋口恵子, 杉野公美, 安立昌篤, 中崎敦夫, 西川俊夫

日本農芸化学会大会講演要旨集(Web)　2019　2019

ISSN： 2186-7976
Facile Enzymatic Synthesis of Phosphatidylthreonine Using an Engineered Phospholipase D

Jasmina Damnjanović, Nozomi Matsunaga, Masaatsu Adachi, Hideo Nakano, Yugo Iwasaki

European Journal of Lipid Science and Technology　120　(6)　2018/06/01
Publisher: Wiley-VCH Verlag
DOI： 10.1002/ejlt.201800089 　

ISSN： 1438-9312 1438-7697
テトロドトキシンの推定生合成中間体の合成研究

宮坂忠親, 安立昌篤, 杉本敬太, 山下まり, 西川俊夫

日本農芸化学会大会講演要旨集(Web)　2018　2018

ISSN： 2186-7976
テトロドトキシンの推定生合成中間体の合成研究

宮坂忠親, 安立昌篤, 杉本敬太, 山下まり, 西川俊夫

有機合成シンポジウム講演予稿集　113th　2018
Differential binding of tetrodotoxin and its derivatives to voltage-sensitive sodium channel subtypes (Na(v)1.1 to Na(v)1.7)

Tadaaki Tsukamoto, Yukie Chiba, Minoru Wakamori, Tomoshi Yamada, Shunsuke Tsunogae, Yuko Cho, Ryo Sakakibara, Takuya Imazu, Shouta Tokoro, Yoshiki Satake, Masaatsu Adachi, Toshio Nishikawa, Mari Yotsu-Yamashita, Keiichi Konoki

BRITISH JOURNAL OF PHARMACOLOGY　174　(21)　3881-3892　2017/11

DOI： 10.1111/bph.13985 　

ISSN： 0007-1188

eISSN： 1476-5381
Differential Binding of Tetrodotoxin and its Derivatives to Voltage-sensitive Sodium Channel Subtypes (Nav1.1 to Nav1.7) Peer-reviewed

Tsukamoto, T, Chiba, Y, Wakamori, M, Yamada, T, Tsunogae, S, Cho, Y, Sakakibara, R, Imazu, T, Tokoro, S, Satake, Y, Adachi, M, Nishikawa, T, Yotsu-Yamashita, M, Konoki, K

Br. J. Pharmacol.　174　3881-3892　2017/08

DOI： 10.1111/bph.1a3985 　
トリクロロアセトアミドからイソニトリルへの新規な一段階変換反応

宮坂忠親, 橋本穂果, 安立昌篤, 西川俊夫

日本農芸化学会大会講演要旨集(Web)　2017　2017

ISSN： 2186-7976
One-Step Transformation of Trichloroacetamide into Isonitrile Peer-reviewed

Masaatsu Adachi, Tadachika Miyasaka, Honoka Hashimoto, Toshio Nishikawa

ORGANIC LETTERS　19　(2)　380-383　2017/01

DOI： 10.1021/acs.orglett.6b03583 　

ISSN： 1523-7060

eISSN： 1523-7052
トリクロロアセトアミドからイソニトリルへの新規な一段階変換反応

宮坂忠親, 橋本穂果, 安立昌篤, 西川俊夫

中部化学関係学協会支部連合秋季大会講演予稿集　47th　2016
Multifunctionality of the N-Trichloroacetyl Group Developed in the Synthesis of Tetrodotoxin, a Puffer Fish Toxin. Invited Peer-reviewed

Nishikawa, T, Urabe, D, Adachi, M, Isobe, M

Synlett　26　1930-1939　2015/07/01
Total Synthesis of Polygalolide A by Intramolecular C-Glycosylation

Masaatsu Adachi

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN　73　(6)　607-615　2015/06

ISSN： 0037-9980
分子内C-グリコシル化反応を利用したPolygalolide Aの全合成 Invited Peer-reviewed

安立昌篤

有機合成化学協会誌　73　607-615　2015/05/01
Asymmetric synthesis of 3-azide-4-fluoro-l-phenylalanine Peer-reviewed

Masaatsu Adachi, Mado Nakajima, Minoru Isobe

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY　79　(5)　707-709　2015/05

DOI： 10.1080/09168451.2014.997185 　

ISSN： 0916-8451

eISSN： 1347-6947
Stereocontrolled Synthesis of ABC Tricycle of Solanoeclepin A Peer-reviewed

Masaatsu Adachi, Mai Torii, Toshio Nishikawa

SYNLETT　26　(7)　965-969　2015/04

DOI： 10.1055/s-0034-1380399 　

ISSN： 0936-5214

eISSN： 1437-2096
A New Deprotection Procedure of MTM Ether Peer-reviewed

Adachi, M, Hashimoto, H, Sakakibara, R, Imazu, T, Nishikawa, T

Synlett　2498-2502　2014/12/01
Synthesis of 5,6,11-Trideoxytetrodotoxin Peer-reviewed

Masaatsu Adachi, Ryo Sakakibara, Yoshiki Satake, Minoru Isobe, Toshio Nishikawa

CHEMISTRY LETTERS　43　(11)　1719-1721　2014/11

DOI： 10.1246/cl.140684 　

ISSN： 0366-7022

eISSN： 1348-0715
インドールアルカロイドセスペンドールの合成研究

樋口恵子, 杉野公美, 中崎敦夫, 安立昌篤, 西川俊夫

日本農芸化学会大会講演要旨集(Web)　2014　2014

ISSN： 2186-7976
Synthesis of 5- and 8-deoxytetrodotoxin Peer-reviewed

Yoshiki Satake, Masaatsu Adachi, Shouta Tokoro, Mari Yotsu-Yamashita, Minoru Isobe, Toshio Nishikawa

Chemistry - An Asian Journal　9　(7)　1922-1932　2014
Publisher: John Wiley and Sons Ltd
DOI： 10.1002/asia.201402202 　

ISSN： 1861-471X 1861-4728
Total Synthesis of Chiriquitoxin, an Analogue of Tetrodotoxin Isolated from the Skin of a Dart Frog Peer-reviewed

Masaatsu Adachi, Takuya Imazu, Ryo Sakakibara, Yoshiki Satake, Minoru Isobe, Toshio Nishikawa

CHEMISTRY-A EUROPEAN JOURNAL　20　(5)　1247-1251　2014/01

DOI： 10.1002/chem.201304110 　

ISSN： 0947-6539

eISSN： 1521-3765
First Identification of 5,11-Dideoxytetrodotoxin in Marine Animals, and Characterization of Major Fragment Ions of Tetrodotoxin and Its Analogs by High Resolution ESI-MS/MS Peer-reviewed

Mari Yotsu-Yamashita, Yuka Abe, Yuta Kudo, Raphael Ritson-Williams, Valerie J. Paul, Keiichi Konoki, Yuko Cho, Masaatsu Adachi, Takuya Imazu, Toshio Nishikawa, Minoru Isobe

MARINE DRUGS　11　(8)　2799-2813　2013/08

DOI： 10.3390/md11082799 　

ISSN： 1660-3397
Stereocontrolled Total Synthesis of Polygalolide A. Peer-reviewed

Yamada, H, Adachi, M, Isobe, M, Nishikawa, T

Chem. Asian. J.　8　1428-1435　2013/04

DOI： 10.1002/asia.201300362. 　
An Improved Synthesis of (-)-5,11-Dideoxytetrodotoxin Peer-reviewed

Masaatsu Adachi, Takuya Imazu, Minoru Isobe, Toshio Nishikawa

JOURNAL OF ORGANIC CHEMISTRY　78　(4)　1699-1705　2013/02

DOI： 10.1021/jo302773f 　

ISSN： 0022-3263
Stereocontrolled synthesis of the oxathiabicyclo[3.3.1] nonane core structure of tagetitoxin Peer-reviewed

Hitomi Yamada, Masaatsu Adachi, Toshio Nishikawa

CHEMICAL COMMUNICATIONS　49　(95)　11221-11223　2013

DOI： 10.1039/c3cc46949b 　

ISSN： 1359-7345

eISSN： 1364-548X
A Concise Synthesis of a Highly Strained Cyclobutane in Solanoeclepin A by Radical Cyclization Peer-reviewed

Takema Komada, Masaatsu Adachi, Toshio Nishikawa

CHEMISTRY LETTERS　41　(3)　287-289　2012/03

DOI： 10.1246/cl.2012.287 　

ISSN： 0366-7022

eISSN： 1348-0715
Stereocontrolled Synthesis of an Indole Moiety of Sespendole and Stereochemical Assignment of the Side Chain Peer-reviewed

Masaatsu Adachi, Keiko Higuchi, Nopporn Thasana, Hitomi Yamada, Toshio Nishikawa

ORGANIC LETTERS　14　(1)　114-117　2012/01

DOI： 10.1021/ol202895u 　

ISSN： 1523-7060
Total Synthesis of Polygalolide A Peer-reviewed

Masaatsu Adachi, Hitomi Yamada, Minoru Isobe, Toshio Nishikawa

Org. Lett.　10.1021/ol2028256　2011/11/18
A New Ring Expansion for a Chiral Hexahydroazulene Skeleton Possessing an Angular Methyl Group Peer-reviewed

Masaatsu Adachi, Takema Komada, Toshio Nishikawa

J. Org. Chem.　(76)　6942-6945　2011/07/01
インドールアルカロイドSespendole芳香族部分の合成研究

樋口恵子, NOPPORN Thasana, 杉野公美, 安立昌篤, 中崎敦夫, 西川俊夫

中部化学関係学協会支部連合秋季大会講演予稿集　42nd　2011
Synthesis of an Advanced Intermediate Bearing Two Hydroxy Groups for (-)-Tetrodotoxin and Its Analogs Peer-reviewed

Toshio Nishikawa, Yuya Koide, Masaatsu Adachi, Minoru Isobe

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN　83　(1)　66-68　2010/01

DOI： 10.1246/bcsj.20090223 　

ISSN： 0009-2673

eISSN： 1348-0634
Novel Stereocontrolled Synthesis of Highly Functionalized Cyclobutanes by Epoxide Opening through a Carbanion Intermediate in Heteroconjugate Addition Peer-reviewed

Masaatsu Adachi, Eiji Yamauchi, Takema Komada, Minoru Isobe

SYNLETT　(7)　1157-1161　2009/04

DOI： 10.1055/s-0028-1088108 　

ISSN： 0936-5214
Streptomyces phospholipase D mutants with altered substrate specificity capable of phosphatidylinositol synthesis Peer-reviewed

Atsushi Masayama, Tetsuya Takahashi, Kaori Tsukada, Seigo Nishikawa, Rie Takahashi, Masaatsu Adach, Kazushi Koga, Atsuo Suzuki, Takashi Yamane, Hideo Nakano, Yugo Iwasaki

CHEMBIOCHEM　9　(6)　974-981　2008/04

DOI： 10.1002/cbic.200700528 　

ISSN： 1439-4227

eISSN： 1439-7633
N-heterocyclic carbenes catalyzed umpolung reactions via homoenolates Peer-reviewed

Masaatsu Adachi

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN　65　(10)　1009-1010　2007/10

ISSN： 0037-9980
Degradation and reconstruction of moenomycin A and derivatives: Dissecting the function of the isoprenoid chain Peer-reviewed

Masaatsu Adachi, Yi Zhang, Catherine Leimkuhler, Binyuan Sun, John V. LaTour, Daniel E. Kahne

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY　128　(43)　14012-14013　2006/11

DOI： 10.1021/ja065905c 　

ISSN： 0002-7863
Synthetic study of alpha(2,8) oligosialoside using N-Troc sialyl N-phenyltrifluoroimidate Peer-reviewed

H Tanaka, Y Nishiura, M Adachi, T Takahashi

HETEROCYCLES　67　(1)　107-112　2006/01

ISSN： 0385-5414
One-Pot Synthesis of Sialo-Containing Glycosyl Amino Acids Using N-Troc β-Thiophenyl Sialoside.

Hiroshi Tanaka, Masaatsu Adachi, Takashi Takahashi

Chemistry - a Europian Journal　11　(3)　849-862　2005

DOI： 10.1002/chem.200400840 　

ISSN： 0947-6539
Efficient Stereoselective Synthesis of γ-N-Glycosyl Asparagines by N-Glycosylation of Primary Amide Groups. Peer-reviewed

Hiroshi Tanaka, Yuki Iwata, Daisuke Takahashi, Masaatsu Adachi, Takashi Takahashi

J. Am. Chem. Soc.　127, 1630-1631　2005
One-pot Synthesis of Sialo-containing Glycosyl Amino Acids by Use of an N-Trichloroethoxycarbonyl-β-thiophenyl Sialoside. Peer-reviewed

Hiroshi Tanaka, Masaatsu Adachi, Takashi Takahashi

Chem. Eur. J.　11, 849-862　2005
An effective sialylation method using N-Troc- and N-Fmoc-protected beta-thiophenyl sialosides and application to the one-pot two-step synthesis of 2,6-sialyl-T antigen Peer-reviewed

M Adachi, H Tanaka, T Takahashi

SYNLETT　(4)　609-614　2004/03

DOI： 10.1055/s-2004-817759 　

ISSN： 0936-5214
Efficient Stereoselective Synthesis of N-Linked Glycopeptides by N-Glycosylation of Primary Amide Groups

Hiroshi Tanaka, Yuki Iwata, Daisuke Takahashi, Masaatsu Adachi, Takashi Takahashi

Glycobiology　14　(11)　1088　2004
Effective sialylation method using N-Troc and N-Fmoc β-phenyl thiosialosides and an application to the one-pot two-step synthesis of 2,6-STF Antigen

Masaatsu Adachi, Hiroshi Tanaka, Takashi Takahashi

Synlett　609-614　2004
Efficient Synthesis of Core 2 Class Glycosyl Amino Acids by One-pot Glycosylation Approach. Peer-reviewed

Hiroshi Tanaka, Masaatsu Adachi, Takashi Takahashi

Tetrahedron Lett.　45, 1433-1436　2004
Efficient Synthesis of Core 2 Class Glycosyl Amino Acids by One-pot Glycosylation Approach. Peer-reviewed

Hiroshi Tanaka, Masaatsu Adachi, Hirokazu Tsukamoto, Takeji Ikeda, Haruo Yamada, Takashi Takahashi

Org. Lett.　4, 4213-4216.　2002
Combinatorial synthesis of trisaccharides via solution-phase one-pot glycosylation Peer-reviewed

T Takahashi, M Adachi, A Matsuda, T Doi

TETRAHEDRON LETTERS　41　(15)　2599-2603　2000/04

ISSN： 0040-4039

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Books and Other Publications 1

*C-Glycosylation, Chemical Glycosylation Reactions, In Glycoscience, 2nd edition

Toshio Nishikawa, Masaatsu Adachi, Minoru Isobe

Springer Verlag　2008

Research Projects 11

植物寄生性農害虫孵化促進活性を有する歪んだ架橋型多環性天然物の合成研究

安立昌篤

Offer Organization: 日本学術振興会

System: 科学研究費助成事業

Category: 基盤研究(C)

Institution: 東北大学

2021/04/01 - 2024/03/31

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本研究では、特異かつ高度に歪んだ架橋型多環性骨格を合成して、生理活性の詳細が未だ明らかにされていない希少天然有機化合物の収束的な化学合成と系統的な構造活性相関研究を目的としている。具体的には、植物寄生性農害虫であるジャガイモシスト線虫の孵化機構において重要な因子であり、高度に歪んだシクロブタン骨格を含むソラノエクレピンAの合成研究を行う。ソラノエクレピンAは、三員環から七員環までの全ての炭素環からなる非常に特異な化学構造を有している。特に、生理活性発現に必須であると考えられる右側部分は、連続する不斉四級炭素を含み高度に歪んだシクロブタンからなるトリシクロ[5.2.1.01,6]デカン(DEF環)であるため、その合成は極めて挑戦的である。この本研究では、4-exo-trig型ラジカル環化反応を機軸として、高度に多官能基化されたシクロブタンを含む特異な架橋型多環性骨格の効率的な合成法を確立する同時に、収束的な合成経路の開発によってソラノエクレピンAおよびその関連化合物(構造単純化アナログ)の化学合成による量的供給を目的としている。さらに、ソラノエクレピンAの合成経路を確立した後は、シスト線虫孵化促進活性を保持した単純化アナログの設計を目指す。一部の環構造や官能基を省略した構造単純化セグメントを左右それぞれ用意し、系統的な誘導体（右側あるいは左側単純化アナログ）を合成する。系統的な構造活性相関研究を展開することで、孵化の分子機構解明とシスト線虫駆除剤のリード化合物の創出を目指す。
Collective synthesis of natural products and elucidation of its biological functions

NISHIKAWA Toshio

Offer Organization: Japan Society for the Promotion of Science

System: Grants-in-Aid for Scientific Research

Category: Grant-in-Aid for Scientific Research (B)

Institution: Nagoya University

2019/04/01 - 2022/03/31

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This research aims at collective synthesis of structurally complex natural products whose biological activities have not been reported, and explore of the unique and potent biological activities and its application to medicine or biochemical tools. We first synthesized seven cyclic guanidinium compounds isolated as candidates of the biosynthetic intermediates from pufferfish or newts. Next, we successfully developed construction of the core skeleton of chartellines, alkaloid possessing indolenine, imidazole, and beta-lactam. Third, six analogs of oscillatoxin/aplysiatoxin, marine polyketide, were synthesized from a same intermediate in a few steps. Most of those are the first chemical synthesis of the natural analogs, and discovery of new biological activity is anticipated.
特異な生態機構を制御する寄主植物由来超微量多環性天然有機化合物の合成研究 Competitive

安立昌篤

Offer Organization: 日本学術振興会

System: 科学研究費助成事業

Category: 基盤研究(C)

2018/04 - 2021/03
ラジカル反応を機軸としたジャガイモシスト線虫孵化促進物質の合成研究 Competitive

Offer Organization: 日本学術振興会

System: 科学研究費助成事業

Category: 基盤研究(C)

2015/04 - 2018/03
Control of ion-channel functions by analogues of natural toxins

Nishikawa Toshio, Konoki Kei-ichi, Adachi Masaatsu

Offer Organization: Japan Society for the Promotion of Science

System: Grants-in-Aid for Scientific Research

Category: Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)

Institution: Nagoya University

2011/04/01 - 2016/03/31

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Tetrodotoxin, a puffer fish toxin, inhibits voltage-gated sodium channel (VSGC), a key protein of neurotransmission, however, dose not show subtype selectivity. Purpose of this research is to find a new subtype selective inhibitor of VGSCs, by synthesizing a dozen analogues of TTX. However, slight modification of TTX decreases the inhibitory activity of VGSC. On the other hand, we found that crambesin B carboxylic acid, a marine natural product, exhibits potent inhibition comparable to TTX for the first time.
高度に歪んだ架橋型多環性骨格構築法の開発と植物寄生性線虫孵化促進化合物の合成研究 Competitive

安立昌篤

Offer Organization: 日本学術振興会

System: 科学研究費助成事業

Category: 基盤研究(C)

2012/04 - 2015/03

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本研究では、特異な架橋型多環性骨格の効率的な合成法を開発し、生理活性の詳細が明らかにされていない希少天然有機化合物の化学合成を目的としている。具体的には、農害虫であるジャガイモシスト線虫の孵化機構において重要な因子であり、高度に歪んだシクロブタン骨格を含むソラノエクレピンAの合成研究を行う。
Synthetic study on bioactive natural product, causing hatching phenomenon toward potato Cyst nematodes, by construction of highly-substituted cyclobutane skeleton

ADACHI Masaatsu

Offer Organization: Japan Society for the Promotion of Science

System: Grants-in-Aid for Scientific Research

Category: Grant-in-Aid for Young Scientists (B)

Institution: Nagoya University

2010 - 2011

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Synthesis of solanoeclepin A, the most active hatching agent of potato cyst nematode isolated from hydroponic potato cultures was examined not only for the chemical supply of solanoeclepin A but also for the structure-activity relationship study. As a result, the new ring expansion reaction was discovered for the synthesis of a chiral hexahydroazulene skeleton possessing an angular methyl group. Furthermore, synthesis of oxabicylo skeleton, corresponding to the left-hand nucleus, was also achieved.
Synthetic Studies on biologically active natural products containing novel heterocyclic structures

NISHIKAWA Toshio, ADACHI Masaatsu, NAKAZAKI Atsuo

Offer Organization: Japan Society for the Promotion of Science

System: Grants-in-Aid for Scientific Research

Category: Grant-in-Aid for Scientific Research (B)

Institution: Nagoya University

2008 - 2011

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Synthetic methodologies of natural products containing novel heterocyclic structures have been developed ; synthetic routes of the skeletons of pactamycin and tagetitoxin were established, and total synthesis of decarbamoyl-α-saxitoxinol and polygalolide A was achieved.
分子内C-グリコシル化反応を用いるオキサビシクロ骨格の効率的構築法の開発 Competitive

安立昌篤

System: 科学研究費助成事業

Category: 19880013

2007/04 - 2009/03
The Innovative Synthesis of Bioactive Molecules based on the Molecular Mechanism of Natural Products Activity

ISOBE Minoru, ICHIKAWA Yoshiyasu, NISHIKAWA Toshio, KUSE Masaki, KAI Hidenori, ADACHI Masaatsu

Offer Organization: Japan Society for the Promotion of Science

System: Grants-in-Aid for Scientific Research

Category: Grant-in-Aid for Specially Promoted Research

Institution: Nagoya University

2004 - 2008
グリカール分子変換反応による官能基化環状骨格の構築と生理活性天然物の合成研究 Competitive

安立昌篤

System: 科学研究費助成事業

Category: 若手研究(B)，課題番号：20780082

2008 -

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