北海道大学大学院 理学研究院化学部門

有機反応論研究室

PUBLICATION

2020

Fungal-derived Brevianamide assembly by a stereoselective semi-pinacolase. Ying Ye, Lei Du, Xingwang Zhang, Sean A. Newmister, Morgan McCauley, Juan V. Alegre-Requena, Wei Zhang, Shuai Mu, Atsushi Minami, Amy E. Fraley, Maria L. Adrover-Castellano, Nolan A. Carney, Vikram V. Shende, Feifei Qi, Hideaki Oikawa, Hikaru Kato, Sachiko Tsukamoto, Robert S. Paton, Robert M. Williams, David H. Sherman, and Shengying Li, Nature Catalysis, accepted.

Oxidative Ring Contraction by a Multifunctional Dioxygenase Generates the Core Cycloocatadiene in the Biosynthesis of Fungal Dimeric Anhydride Zopfiellin. Tetsuya Shiina, Taro Ozaki, Yusuke Matsu, Shota Nagamine, Chengwei Liu, Masaru Hashimoto, Atsushi Minami, Hideaki Oikawa, Organic Letters, 2020, 22, 5, 1997-2001 DOI: 10.1021/acs.orglett.0c00340
Total synthesis of alkaloids using both chemical and biochemical methods. Ryo Tanifuji, Atsushi Minami,  Hiroki Oguri, Hideaki Oikawa, Natural Product Reports, 2020  DOI: 10.1039/c9np00073a
Reconstitution of biosynthetic machinery of fungal natural products in heterologous hosts. Oikawa H., Biosci Biotechnol Biochem., 2020, 84, 433-444 DOI: 10.1080/09168451.2019.1690976

2019

Biosynthetic study of conidiation-inducing factor conidiogenone: heterologous production and cyclization mechanism of a key bifunctional diterpene synthase. Shiina, T.; Nakagawa, K.; Fujisaki, Y.; Ozaki, T.; Liu, C.; Toyomasu, T.; Hashimoto, M.; Koshino, H.; Minami, A.; Kawaide, H.; Oikawa, H.; Biosci Biotechnol Biochem. 2019, 83(2), 192-201. DOI: 10.1080/09168451.2018.1536518 
BBB Awards for Excellence to Authors (2019) Vol. 83 受賞

Efficient reconstitution of Basidiomycota diterpene erinacine gene cluster in Ascomycota host Aspergillus oryzae based on genomic DNA sequences. Liu, C.; Minami, A.; Ozaki, T.; Wu, J.; Kawagishi, H.; Maruyama, J.; Oikawa, H.; J. Am. Chem. Soc. 2019, 141, 39, 15519-15523 DOI: 10.1021/jacs.9b08935


Ascomycota Aspergillus oryzae is an efficient expression host for production of Basidiomycota terpenes using genomic DNA sequences. Nagamine, S.; Nishishita, J.; Kozaki, T.; Sogahata, K.; Sato, Y.; Minami, A.; Liu, C.; Ozaki, T.; Schmidt-Dannert, C.; Maruyama, J.; Oikawa, H.; Appl. Environ. Microbiol., 2019. DOI: 10.1128/AEM.00409-19
Heterologous production of asperipin-2a: Proposal for sequential oxidative macrocyclization by a fungi-specific DUF3328 oxidase. Ye, Y.; Ozaki, T.; Umemura, M.; Liu, C.; Minami, A.; Oikawa, H.; Org. Biomol. Chem. 2019, 17, 39-43 DOI: 10.1039/C8OB02824A
Biosynthetic machinery of 6‐hydroxymellein derivatives leading to cyclohelminthols and palmaenones. Ugai, T.; Minami, A.; Tanaka, S.; Ozaki, T.; Liu, C.; Shigemori, H.; Hashimoto, M.; Oikawa, H.; ChemBioChem. 2019. DOI: 10.1002/cbic.201900404

Zn(OTf)2 mediated annulations of <i>N</i>-propargylated tetrahydrocarbolines: divergent synthesis of four distinct alkaloidal scaffolds. Yorimoto, S.; Tsubouchi, A; Mizoguchi, H.; Oikawa, H.; Tsunekawa, Y.; Ichino, T.; Maeda, S.; Oguri, H.; Chem.2019, 10, 5686-5698 DOI: 10.1039/C9SC01507H
Elucidation of biosynthetic pathway of a plant hormone abscisic acid in phytopathogenic fungi. Takino, J.; Kozaki, T.; Ozaki, T.; Liu, C.; Minami, A.; Oikawa, H.; Biosci. Biotech. Biochem. 2019, 83, 1642-1649 DOI: 10.1080/09168451.2019.1618700
Generation of C5-desoxy analogs of tetrahydroisoquinoline alkaloids exhibiting potent DNA alkylating ability. Tanifuji, R.; Tsukakoshi, K.; Ikebukuro, K.; Oikawa, H.; Oguri, H.; Bioorg. Med. Chem. Lett. 2019, 29, 1807-1811 https://doi.org/10.1016/j.bmcl.2019.05.009
【著書】
Biosynthesis of Indole Diterpenes
C. Liu, A. Minami, T. Ozaki, and H. Oikawa
Comprehensive Natural Products Ⅲ: Chemistry and Biology, H.-W. Liu and T. Begley, Ed., Elsevier, In press
Sesterterpene Biosynthesis: Cyclization Mechanisms and Oxidative Modifications
A. Minami, T. Ozaki, C. Liu, and H. Oikawa
Comprehensive Natural Products Ⅲ: Chemistry and Biology, H.-W. Liu and T. Begley, Ed., Elsevier, In press

【総説・解説など
糸状菌による植物ホルモンアブシジン酸の生合成:新奇な環化酵素の発見とその環化機構の解明、南篤志、尾﨑太郎、劉成偉、及川英秋 バイオサイエンスとインダストリー、Vol77.NO2, 136-138 (2019)

2018

Unveiling Biosynthesis of the Phytohormone Abscisic Acid in Fungi: Unprecedented Mechanism of Core Scaffold Formation Catalyzed by an Unusual Sesquiterpene Synthase. Takino, J.; Kozaki, T.; Sato, Y.; Liu, C.; Ozaki, T.; Minami, A.; Oikawa, H.; J. Am. Chem. Soc. 2018, 140, 12392–12395  DOI: 10.1021/jacs.8b08925
Enzymatic formation of a skipped methyl-substituted octaprenyl side chain of longestin (KS-505a): Involvement of homo-IPP as a common extender unit. Ozaki, T.; Shinde, S. S.; Gao, L.; Okuizumi, R.; Liu, C.; Ogasawara, Y.; Lei, X.; Dairi, T.; Minami, A.; Oikawa, H.; Angew. Chem. Int. Ed. Engl. 2018, 57, 6629-6632 DOI: 10.1002/anie.201802116

Chemo-enzymatic Total Syntheses of Jorunnamycin A, SaframycinA, and N‑Fmoc Saframycin Y3. Tanifuji, R.; Koketsu, K.; Takakura, M.; Asano, R.; Minami, A.; Oikawa, H.; Oguri, H.; J. Am. Chem. Soc. 2018, 140, 10705–10709 DOI: 10.1021/jacs.8b07161
Cyclopentane forming di-/sesterterpene synthases: widely distributed enzymes in bacteria, fungi and plants. Minami, A.; Ozaki, T.; Liu, C.; Oikawa, H.; Nat. Prod. Rep. 2018, 35, 1330-1346 DOI: 10.1039/C8NP00026C
Total Biosynthesis of Brassicicenes: Identification of a Key Enzyme for Skeletal Diversification. Tazawa, A.; Ye, Y.; Ozaki, T.; Liu, C.; Ogasawara, Y.; Dairi, T.; Higuchi, Y.; Kato, N.; Gomi, K.; Minami, A.; Oikawa, H.; Org. lett. 2018, 20, 6178-6182 DOI: 10.1021/acs.orglett.8b02654
Design and De Novo Synthesis of 6-Aza-artemisinins. Bonepally, K. R.; Hiruma, T.; Mizoguchi, H.; Ochiai, K.; Suzuki, S.; Oikawa, H.; Ishiyama, A.; Hokari, R.; Iwatsuki, M.; Otoguro, K.; O̅mura, S.; Oguri, H.; Organic letters. 2018, 20, 4667-4671 DOI: 10.1021/acs.orglett.8b01987   
Heterologous biosynthesis of fungal indole sesquiterpene sespendole. Kudo, K; Liu, C.; Matsumoto, T.; Minami, A.; Ozaki, T.; Toshima, H.; Gomi, K.; Oikawa, H.; ChemBioChem 2018, 19, 1492-1497 DOI: 10.1002/cbic.201800187

Theoretical Study of Sesterfisherol Biosynthesis: Computational Prediction of Key Amino Acid Residue in Terpene Synthase. Sato, H.; Narita, K.; Minami, A.; Yamazaki, M.; Wang, C.; Suemune, H.; Nagano, S.; Tomita, T.; Oikawa, H.; Uchiyama, M.; Sci. Rep. 2018, 8, 2473 DOI: 10.1038/s41598-018-20916-x
Total biosynthesis of antiangiogenic agent (-)-terpestacin by artificial reconstitution of the biosynthetic machinery in Aspergillus oryzae. Narita, K.; Minami, A.; Ozaki, T.; Liu, C.; Kodama, M.; Oikawa, H.; J. Org. Chem. 2018, 83, 7042-7048 DOI: 10.1021/acs.joc.7b03220 

 Identification of novel sesterterpenes by genome mining of phytopathogenic fungi Phoma and Colletotrichum sp. Gao, L.; Narita, K.; Ozaki, Kumakura, N.; Gan, P.; Minami, A.; Liu, C.; Lei, X.; Shirasu, K.; Oikawa, H.; Tetrahedron Lett. 2018, 59, 1136-1139 DOI: 10.1016/j.tetlet.2018.02.022
Subcellular localization of aphidicolin biosynthetic enzymes heterologously expressed in Aspergillus oryzae. Ban, A.; Tanaka, M.; Fujii, R.; Minami, A.; Oikawa, H.; Shintani,  T.; Gomi, K.; Biosci. Biotech. Bioch. 2018, 82, 139-147 DOI: 10.1080/09168451.2017.1399789
Biosynthetic study of conidiation-inducing factor conidiogenone: Heterologous production and cyclization mechanism of a key bifunctional diterpene synthase. Shiina, T.; Nakagawa, K.; Fujisaki, Y.; Ozaki, T.; Liu, C.; Toyomasu, T.; Hashimoto, M.; Koshino, H.; Minami, A.; Kawaide, H.; Oikawa, H.; Biosci. Biotechnol. Biochem. 2018, DOI: 10.1080/09168451.2018.1536518
【総説・解説など】
ゲノム情報を用いたC20/C25テルペン環化酵素遺伝子の網羅的発現による新規天然物の生産
南篤志、尾﨑太郎、劉成偉、及川英秋
バイオサイエンスとインダストリー、Vol76.NO1,(2018)
【著書】
書名:酵母菌・麹菌・乳酸菌の産業応用展開
麹菌を宿主としたカビの二次代謝産物の生産
南篤志、劉成偉、尾﨑太郎、及川英秋
シーエムシー出版

2017

Focused Genome Mining of Structurally Related Sesterterpenes: Enzymatic Formation of Enantiomeric and Diastereomeric Products. Narita, K.; Sato, H.; Minami, A.; Kudo, K.; Gao, L.; Liu, C.; Ozaki, T.; Kodama, M.; Lei, X.; Taniguchi, T.; Monde, K.; Yamazaki, M.; Uchiyama, M.; Oikawa, H.; Org. Lett. 2017, 19, 6696-6699 DOI: 10.1021/acs.orglett.7b03418
Stepwise cyclopropanation on the polycyclopropanated polyketide formation in jawsamycin biosynthesis. Hiratsuka, T.; Suzuki, H.; Minami, A.; Oikawa, H.; Org. Biomol. Chem. 2017,15,1076-1079 DOI: 10.1039/C6OB02675C
Dissection of goadsporin biosynthesis by in vitro reconstitution leading to designer analogues expressed in vivo. Ozaki, T.; Yamashita, K..; Goto, Y.; Shimomura, M.; Hayashi, S.; Asamizu, S.; Sugai, Y.; Ikeda, H.; Suga, H.; Onaka, H.; Nat. Commun. 2017, 8, 14207-14207 DOI:10.1038/ncomms14207

Cyclization mechanism of phomopsene synthase: mass spectrometry based analysis of various site-specifically labeled terpenes. Shinde, S. S.; Minami, A.; Chen, Z.; Tokiwano, T.; Toyomasu, T.; Kato, N.; Sassa, T.; Oikawa, H.; J. antibiot. 2017,70,632-638 DOI: 10.1038/ja.2017.27
Biosynthetic machinery of diterpene pleuromutilin isolated from basidiomycete fungi. Yamane, M.; Minami, A.; Liu, C.; Ozaki, T.; Takeuchi, I.; Tsukagoshi, T.; Tokiwano, T.; Gomi, K.; Oikawa, H.; ChemBioChem 2017, 18, 2317-2322 DOI: 10.1002/cbic.201700434

2016

Discovery and Total Synthesis of Streptoaminals: Antimicrobial [5,5]-Spirohemiaminals from the Combined-Culture of Streptomyces nigrescens and Tsukamurella pulmonis. Sugiyama, R.; Nishimura, S.; Ozaki, T.; Asamizu, S.; Onaka, H.; Kakeya, H.; Angew. Chemi. Int. Edit. 201655, 10278-10282 DOI: 10.1002/anie.201604126
Unveiling the Biosynthetic Pathway of the Ribosomally Synthesized and Post-translationally Modified Peptide Ustiloxin B in Filamentous Fungi. Ye, Y.; Minami, A.; Igarashi, Y.; Izumikawa, M.; Umemura, M.; Nagano, N.; Machida, M.; Kawahara, T.; Shin-ya, K.; Gomi, K.; Oikawa, H.; Angew. Chem. Int. Ed. 2016, 55, 8072-8075  DOI: 10.1002/anie.201602611
Multiple Oxidative Modifications in the Ophiobolin Biosynthesis: P450 Oxidations Found in Genome Mining. Narita, K.; Chiba, R.; Minami, A.; Kodama, M.; Fujii, I.; Gomi, K.; Oikawa, H.Org. Lett. 2016, 18, 1980-1983  DOI: 10.1021/acs.orglett.6b00552
Biosynthesis of Shearinine: Diversification of a Tandem Prenyl Moiety of Fungal Indole Diterpenes. Liu, C. W.; Minami, A.; Dairi, T.; Gomi, K.; Scott, Barry, S.; Oikawa, H. Org. Lett. 2016, 18, 5026−5029  DOI: 10.1021/acs.orglett.6b02482
Genome mining approach harnessing the cryptic gene cluster in Alternaria solani: Production of PKS-NRPS hybrid metabolite, didymellamide B. Ugai, T.; Minami, A.; Gomi, K.; Oikawa, H.; Tetrahedron Lett. 2016, 57, 2793-2796  DOI: 10.1016/j.tetlet.2016.05.043
Insights into the Biosynthesis of Dehydroalanines in Goadsporin. Ozaki, T.; Kurokawa, Y.; Hayashi, S.; Oku, N.; Asamizu, S.; Igarashi, Y.; Onaka, H.; Chembiochem. 201617, 218-223 DOI: 10.1002/cbic.201500541
Reconstitution of biosynthetic machinery of fungal polyketides: unexpected oxidations of biosynthetic intermediates by expression host. Fujii, R.; Ugai, T.; Ichinose, H.; Hatakeyama, M.; Kosaki, T.; Gomi, K.; Fujii, I.; Minami, A.; Oikawa, H. Biosci. Biotechnol. Biochem. 2016, 80, 426-431 DOI: 10.1080/09168451.2015.1104234.
Catalytic asymmetric synthesis of the common amino acid component in the biosynthesis of tetrahydroisoquinoline alkaloids. Tanifuji, R.; Oguri, H.; Koketsu, K.; Yoshinaga, Y.; Minami, A.; Oikawa, H. Tetrahedron Lett. 2016, 57, 623-626 DOI:10.1016/j.tetlet.2015.12.110

【総説・解説など】
Total Biosynthesis of Fungal Indole Diterpenes Using Cell Factories. Minami, A.; Liu, C.; Oikawa, H. Heterocycles. 2016, 92, 397-421 DOI: 10.3987/REV-15-830
Recent advances of Diels–Alderases involved in natural product biosynthesis. Minami, A; Oikawa, H. J. Antibiot. 2016, 69, 500-506 DOI: 10.1038/ja.2016.67.
Nature’s Strategy for Catalyzing Diels-Alder Reaction. Oikawa, H.; Cell Chem. Biol. 2016, 23, 429-430 DOI: 10.1016/j.chembiol.2016.04.002
Exploring the diversification mechanism of skeletal construction in representative natural product families. Oikawa, H.; Tang, Y.; J. Antibiot201669, 471-472 DOI: 10.1038/ja.2016.69

2015

Reconstitution of biosynthetic machinery for highly elaborated indole diterpene penitrem.Liu, C. W.; Tagami, K.; Minami, A.; Matsumoto, T.; Frisvad, J. C.; Suzuki, H.; Ishikawa,J.; Gomi, K.; and Oikawa, H. Angew. Chem. Int. Ed. 2015, 54, 5748-5752 DOI: 10.1002/anie.201502797 
Genome Mining for Sesterterpenes Using Bifunctional Terpene Synthases Reveals a Unified Intermediate of Di/Sesterterpenes.Ye, Y.; Minami, A.; Mandi, A.; Liu, C.; Taniguchi, T.; Kuzuyama, T.;Monde, K.; Gomi, K.; Oikawa, H. J. Am. Chem. Soc. 2015, 137, 11846-11853 DOI: 10.1021/jacs.5b08319
Biosynthetic Study on Antihypercholesterolemic Agent Phomoidride: General Biogenesis of Fungal Dimeric Anhydrides.Fujii, R.; Matsu, Y.; Minami, A.; Nagamine, S.; Takeuchi, I.; Gomi, K.; Oikawa, H.Org. Lett. 2015, 17, 5658-5661 DOI: 10.1021/acs.orglett.5b02934
Heterologous Expression of Highly Reducing Polyketide Synthase Involved in Betaenone Biosynthesis.Ugai, T.;Minami, A.; Fujii, R.; Tanaka, M.; Oguri, H.; Gomi, K.; Oikawa, H.Chem.Commun. 2015, 51, 1878-1881 DOI: 10.1039/C4CC09512J
Minimum Information about a Biosynthetic Gene cluster.Medema, M. H.; Kottmann, R.; Yilmaz, P.; Cummings, M.; Biggins, J. B.; Blin, K.; de Bruijn, I.; Chooi, Y. H.; Claesen, J.; Coates, R. C.; Cruz-Morales, P.; Duddela, S.; Dusterhus, S.; Edwards, D. J.; Fewer, D. P.; Garg, N.; Geiger, C.; Gomez-Escribano, J. P.; Greule, A.; Hadjithomas, M.; Haines, A. S.; Helfrich, E. J. N.; Hillwig, M. L.; Ishida, K.; Jones, A. C.; Jones, C. S.; Jungmann, K.; Kegler, C.; Kim, H. U.; Kotter, P.; Krug, D.; Masschelein, J.; Melnik, A. V.; Mantovani, S. M.; Monroe, E. A.; Moore, M.; Moss, N.; Nutzmann, H. W.; Pan, G. H.; Pati, A.; Petras, D.; Reen, F. J.; Rosconi, F.; Rui, Z.; Tian, Z. H.; Tobias, N. J.; Tsunematsu, Y.; Wiemann, P.; Wyckoff, E.; Yan, X. H.; Yim, G.; Yu, F. G.; Xie, Y. C.; Aigle, B.; Apel, A. K.; Balibar, C. J.; Balskus, E. P.; Barona-Gomez, F.; Bechthold, A.; Bode, H. B.; Borriss, R.; Brady, S. F.; Brakhage, A. A.; Caffrey, P.; Cheng, Y. Q.; Clardy, J.; Cox, R. J.; De Mot, R.; Donadio, S.; Donia, M. S.; van der Donk, W. A.; Dorrestein, P. C.; Doyle, S.; Driessen, A. J. M.; Ehling-Schulz, M.; Entian, K. D.; Fischbach, M. A.; Gerwick, L.; Gerwick, W. H.; Gross, H.; Gust, B.; Hertweck, C.; Hofte, M.; Jensen, S. E.; Ju, J. H.; Katz, L.; Kaysser, L.; Klassen, J. L.; Keller, N. P.; Kormanec, J.; Kuipers, O. P.; Kuzuyama, T.; Kyrpides, N. C.; Kwon, H. J.; Lautru, S.; Lavigne, R.; Lee, C. Y.; Linquan, B.; Liu, X. Y.; Liu, W.; Luzhetskyy, A.; Mahmud, T.; Mast, Y.; Mendez, C.; Metsa-Ketela, M.; Micklefield, J.; Mitchell, D. A.; Moore, B. S.; Moreira, L. M.; Muller, R.; Neilan, B. A.; Nett, M.; Nielsen, J.; O'Gara, F.; Oikawa, H.; Osbourn, A.; Osburne, M. S.; Ostash, B.; Payne, S. M.; Pernodet, J. L.; Petricek, M.; Piel, J.; Ploux, O.; Raaijmakers, J. M.; Salas, J. A.; Schmitt, E. K.; Scott, B.; Seipke, R. F.; Shen, B.; Sherman, D. H.; Sivonen, K.; Smanski, M. J.; Sosio, M.; Stegmann, E.; Sussmuth, R. D.; Tahlan, K.; Thomas, C. M.; Tang, Y.; Truman, A. W.; Viaud, M.; Walton, J. D.; Walsh, C. T.; Weber, T.; van Wezel, G. P.; Wilkinson, B.; Willey, J. M.; Wohlleben, W.; Wright, G. D.; Ziemert, N.; Zhang, C. S.; Zotchev, S. B.; Breitling, R.; Takano, E.; Glockner, F. O. Nat. Chem. Biol. 2015, 11, 625-631 DOI:10.1038/nchembio.1890