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

2019

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., accepted. 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. accepted.
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. accepted. 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 BiologyH.-W. Liu and T. Begley, Ed., Elsevier, In press


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