2014
| Biosynthetic Machinery of the Structually Unique Polycyclopropanated Polyketide-Uncleoside Hybrid Jawsamycin(FR-900848).Hiratsuka,T.; Suzuki,H.; Kariya,R.; Seo,T.; Minami,A.; Oikawa,H. Angew. Chem. Int. Ed., 2014, 21, 5423-5426 DOI: 10.1002/anie.201402623 Biogenetically inspired synthesis and skeletal diversification of indole alkaloids.Mizoguchi, H.; Oikawa, H.; Oguri, H. Nat. Chem. 2014, 6, 57-64 DOI:10.1038/nchem.1798 |
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| Allosteric regulation of epoxide opening cascades by a pair of epoxide hydrolases in monensin biosynthesis.Minami, A.; Ose, T.; Sato, K.; Oikawa, A.; Kuroki, K.; Maenaka, K.; Oguri, H.; Oikawa, H.ACS Chem. Biol. 2014, 9, 562-569 DOI: 10.1021/cb4006485 |
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Rapid reconstitution of biosynthetic machinery for fungal metabolites in Aspergillus oryzae: Total biosynthesis of aflatrem.Tagami, K.; Minami, A.; Fujii, R.; Liu, C.; Gomi, K.; Dairi, T.; Oikawa, H. ChemBioChem 2014, 15, 2076-2080 DOI: 10.1002/cbic.201402195 |
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・Functional analysis of a prenyltransferase gene (paxD) in the paxilline biosynthetic gene cluster.Liu, C.; Noike, M.; Minami, A.; Oikawa, H.; Dairi, T. Appl. Microbiol. Biotechnol. 2014, 98, 199-206 DOI:10.1007/s00253-013-4834-9 |
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Nickel-catalyzed dimerization of pyrrolidinoindoline scaffolds: Systematic access to chimonanthines, folicanthines and (+)-WIN 64821.Wada, M.; Murata, T.; Oikawa, H.; Oguri, H. Org. Biomol. Chem. 2014, 12, 298-306 DOI: 10.1039/C3OB41918E |
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A fungal prenyltransferase catalyzes the regular di-prenylation at positions 20 and 21 of paxilline.Liu, C.; Noike, M.; Minami, A.; Oikawa, H.; Dairi, T. Biosci. Biotechnol. Biochem. 2014, 3, 448-454 DOI: 10.1080/09168451.2014.882759. |
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Analysis of enantiofacial selective epoxidation catalyzed by flavin-containing monooxygenase Lsd18 involved in ionophore polyether lasalocid biosynthesis.Suzuki, G.; Minami, A.; Shimaya, M.; Kodama, T.; Morimoto, Y.; Oguri, H.; Oikawa, H. Chem. Lett. 2014, 43, 1779-1781 DOI:10.1246/cl.140721 |
2013
| Reconstitution of biosynthetic machinery for indole-diterpene paxilline in Aspergillus oryzae.Tagami, K.; Liu, C.; Minami, A.; Noike, M.; Isaka, T.; Fueki, S.; Shichijo, Y.; Toshima, H.; Gomi, T.; Dairi, T.; Oikawa, H. J. Am. Chem. Soc. 2013, 135, 1260-1263.DOI: 10.1021/ja3116636 |
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Core assembly mechanism of quinocarcin/SF-1739: Bimodular complex nonribosomal peptide synthetases for sequential mannich-type reactions. Hiratsuka, T.; Koketsu, K.; Minami, A.; Kaneko, S.; Watanabe, C.; Oguri, H.; Watanabe, K.; Oikawa, H. Chem. Biol. 2013, 20, 1523-1535.DOI: http://dx.doi.org/10.1016/j.chembiol.2013.10.011 |
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Identification of ophiobolin F synthase by genome mining approach: a sesterterpene synthase from Aspergillus clavatus.Chiba, R.; Minami, A.; Gomi, K.; Oikawa, H. Org. Lett. 2013, 15, 594-597.DOI: 10.1021/ol303408a |
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Sequential [6+2], [2+2], and [3+2] annulations for rapid assembly of multiple fragments.Mahendar, V.; Oikawa, H.; Oguri, H. Chem. Commun. 2013, 49, 2299-2301. DOI: 10.1039/C2CC38854E |
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Regiospecificities and prenylation mode specificities of the fungal indole diterpene prenyltransferases AtmD and PaxD.Liu, C.; Minami, A.; Noike, M.; Toshima, H.; Oikawa, H.; Dairi, T. Appl. Environ. Microbiol. 2013,79, 7298-7304.DOI: 10.1128/AEM.02496-13 |
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Biosynthetic assembly of cytochalasin backbone.Fujii, R.; Minami, A.; Gomi, K.; Oikawa, H. Tetrahedron Lett. 2013, 54, 2999-3002.DOI:10.1016/j.tetlet.2013.03.120 【総説・解説など】 ・Biosynthetic machinery of ionophore polyether lasalocid: Enzymatic construction of polyether skeleton.Minami, A.; Oguri, H.; Watanabe, K.; Oikawa, H. Curr. Opin. Chem. Biol. 2013, 17, 555-561.DOI:10.1016/j.cbpa.2013.06.004 |
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・生物機能を最大限に利用した天然物の全合成 南 篤志、及川 英秋 現代化学、Vol.7, No.508, 33-38 (2013) |
2012
| Enzymatic catalysis of anti-Baldwin ring closure in polyether biosynthesis.Hotta, K.; Chen, X.; Paton, R. S.; Minami, A.; Li, H.; Swaminathan, K.; Mathews, I. I.; Watanabe, K.; Oikawa, H.; Houk, K. N.; Kim, C. -Y. Nature 2012, 483, 355-358.DOI:10.1038/nature10865 |
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Sequential enzymatic epoxidation involved in polyether lasalocid biosynthesis.Minami, A.; Shimaya, M.; Suzuki, G.; Migita, A.; Shinde, S. S.; Sato, K.; Watanabe, K.; Tamura, T.; Oguri, H.; Oikawa, H. J. Am. Chem. Soc. 2012, 134, 7246-7249.DOI: 10.1021/ja301386g |
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Structure analysis of geranyl pyrophosphate methyltransferase and the proposed reaction mechanism of SAM-dependent C-methylation.Ariyawutthiphan, O.; Ose, T.; Minami, A.; Shinde, S. S.; Tsuda, M.; Gao, Y. -G.; Yao, M.; Oikawa, H.; Tanaka, I. Acta Cryst. 2012, D68, 1558-1569.DOI: 10.1107/S0907444912038486. |
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Hg(OTf)2-catalyzed direct vinylation of tryptamines and versatile Applications for Tandem Reactions.Mizoguchi, H.; Oikawa, H.; Oguri, H. Org. Biomol. Chem. 2012, 4236-4242.DOI: 10.1039/C2OB25236H |
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Parallel and four-step synthesis of natural product-inspired scaffolds through modular assembly and divergent cyclization.Oguri, H.; Mizoguchi, H.; Oikawa, H.; Ishiyama, A.; Iwatsuki, M.; Otoguro, K.; Omura, S. Beilstein J. Org. Chem. 2012, 8, 930-940.DOI:10.3762/bjoc.8.105 |
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【総説・解説など】 Pictet-Spenglerase involved in tetrahydroisoquinoline antibiotic biosynthesis.Koketsu, K.; Minami, A.; Watanabe, K.; Oguri, H.; Oikawa, H. Curr. Opin. Chem. Biol. 2012, 16, 142-149. DOI: 10.1016/j.cbpa.2012.02.021 |
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The Pictet-Spengler mechanism involved in the biosynthesis of tetrahydroisoquinoline antitumor antibiotics: Novel function of non-ribosomal peptide synthetase.Koketsu, K.; Minami, A.; Watanabe, K.; Oguri, H.; Oikawa, H. Method. Enzymol. 2012, 516, 79-98. |
2011
| Generation of anti-trypanosomal agents through concise synthesis and structural diversification of sesquiterpene analogs.Oguri, H.*; Hiruma, T.: Yamagishi, Y.; Oikawa, H.; Ishiyama, A.; Otoguro, K.; Yamada, H.; Omura, S. J. Am. Chem. Soc. 2011, 133, 7096-7105. Selected for the Front Cover.DOI: 10.1021/ja200374q
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| Total biosynthesis of diterpene aphidicolin, a specific inhibitor of DNA polymerase alpha: Heterologous expression of four biosynthetic genes in Aspergillus oryzae.Fujii, R.; Minami, A.; Tsukagoshi, T.; Sato, N.; Sahara, T.; Ohgiya, S.; Gomi, K.; Oikawa, H. Biosci. Biotechnol. Biochem. 2011, 75, 1813-1817.DOI: 10.1271/bbb.110366 |
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Enzymatic epoxide-opening cascades catalyzed by a pair of epoxide hydrolases in the ionophore polyether biosynthesis. Minami, A.; Migita, A.; Inada, D.; Hotta, K.; Watanabe, K.; Oguri, H.; Oikawa, H. Org. Lett. 2011,13, 1638-1641.DOI: 10.1021/ol200100e |
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Dioxygenases, key enzymes to determine the aglycon structures of fusicoccin and brassicicene, diterpene compounds produced by fungi.Ono, Y.; Minami, A.; Noike, M.; Higuchi, Y.; Toyomasu, T.; Sassa, T.; Kato, N.; Dairi, T. J. Am. Chem. Soc. 2011, 133, 2548–2555.DOI: 10.1021/ja107785u |
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Remarkable synergistic effect between MonBI and MonBII on epoxide opening reaction in ionophore polyether monensin biosynthesis.Sato, K.; Minami, A.; Ose, T.; Oguri, H.; Oikawa, H. Tetrahedron Lett. 2011, 52, 5277-5280.DOI:10.1016/j.tetlet.2011.07.145 |
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Involvement of Common Intermediate 3-Hydroxy-L-kyurenine in Chromophore Biosynthesis of Quinomycin Family Antibiotics.Hirose, Y.; Watanabe, K.; Minami, A.; Nakamura, T.; Oguri, H.; Oikawa, H. J. Antibiot. 2011, 64, 117-122.DOI:10.1038/ja.2010.142; |
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Impact of the E540V amino acid substitution in GyrB of Mycobacterium tuberculosis Quinolone Resistance.Kim, H.; Nakajima, C.; Yokoyama, K.; Rahim, Z.; Kim, Y. U.; Oguri, H.; Suzuki, Y. Antimicrobial Agents and Chemotherapy. 2011, 55, 3661-3667.DOI: 10.1128/AAC.00042-11 |
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Crystallization and preliminary X-ray crystallographic study of a methyltransferase involved in 2-methylisoborneol (2-MIB) biosynthesis in Streptomyces lasaliensis.Ariyawutthiphan, O.; Ose, T.; Tsuda, M.; Gao, Y. -G.; Yao, M.; Minami, A.; Oikawa, H.; Tanaka, I. Acta Crystallogr. Sect F Struct. Biol. Cryst. Commun. 2011, 67, 417–420.DOI:10.1107/S1744309110051523 |
2010
| Reconstruction of the saframycin core scaffold defines dual Pictet-Spengler mechanisms.Koketsu, K.; Watanabe, K.; Suda, H.; Oguri, H.; Oikawa, H. Nat. Chem. Biol., 2010, 6, 408-410. |
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| Intriguing Substrate Tolearance of Epoxide Hydrolase Lsd19 Involved in Biosynthesis of the Ionophore Antibiotic Lasalocid A.Matsuura, Y.; Shichijo, Y.; Minami, A.; Migita, A.; Oguri, H.; Watanabe, M.; Tokiwano, T.;Watanabe, K.; Oikawa, H. Org. Lett., 2010, 12, 2226–2229. |
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| Solanapyrone synthase, a possible Diels-Alderase, and iterative type I polyketide synthase encoded in a biosynthetic gene cluster from Alternaria solani.Kasahara, K.; Miyamoto, T.; Fujimoto, T.; Oguri, H.; Tokiwano, T.; Oikawa, H.; Ebizuka, Y.; Fujii, I. ChemBioChem, 2010, 11, 1245-1252. |
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| An anti-tetraamination of a 1,3-diene unit via cascade annulations of the azulenone scaffold with dicarbonyl azo-compounds.Ishigaki, Y.; Mahendar, V.; Oguri, H.; Oikawa, H. Chem. Commun., 2010, 46, 3304-3305. |
| Enzymatic synthesis of molecular skeletons of complex antitumor antibiotics with non-ribosomal peptide synthetases.Watanabe, K.; Oguri, H.; Oikawa, H. J. Synth. Org. Chem., Jpn., 2009, 67, 1152-1160. |
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| Diversification of echinomycin molecular structure by way of chemoenzymatic synthesis and heterologous expression of the engineered echinomycin biosynthetic pathway.Watanabe, K.; Oguri, H.; Oikawa, H. Curr. Opin. Chem. Biol., 2009, 13, 189-196. |
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| Biosynthetic gene-based secondary metabolite screening: a new diterpene, methyl phomopsenonate, from the fungus Phomopsis amygdali.Toyomasu, T.; Kaneko, A.; Tokiwano, T.; Kanno, Y.; Kanno, Y.; Nuda, R.; Miura, S.; Nishioka, T.; Ikeda, C.; Mitsuhashi, W.; Dairi, T.; Kawano, T.; Oikawa, H.; Kato, N.; Sassa, T. J. Org. Chem., 2009, 74, 1541-1548. |
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Rationally Engineered Total Biosynthesis of a Synthetic Analogue of a Natural Quinomycin Depsipeptide in Escherichia coli.Watanabe, K.; Hotta, K.; Praseuth, A. P.; Searcey, M.; Wang, C. C. C.; Oguri, H.; Oikawa, H. Chembiochem, 2009, 10, 1965-1968. |
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| Escherichia coli Allows Efficient Modular Incorporation of Newly Isolated Quinomycin Biosynthetic Enzyme into Echinomycin Biosynthetic Pathway for Rational Design and Synthesis of Potent Antibiotic Unnatural Natural Product.Watanabe, K.; Hotta, K.; Nakaya, M.; Praseuth, A. P.; Wang, C. C. C.; Inada, D.; Takahashi, K.; Fukushi, E.; Oguri, H.; Oikawa, H. J. Am. Chem. Soc., 2009, 131, 9347-9353. |
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| Divergent and Expeditious Access to Fused Skeletons Inspired by Indole Alkaloids and Transtaganolides.Mizoguchi, H.; Oguri, H.; Tsuge, K.; Oikawa, H. Organic Letters, 2009, 11, 3016-3019. |
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| Identification and functional analysis of brassicicene C biosynthetic gene cluster in Alternaria brassicicola.Minami, A.: Tajima, N.; Higuchi, Y.; Toyomasu, T.; Sassa, T.; Kato, N.; Dairi, T. Bioorg. Med. Chem. Lett. 2009, 19, 870-874. |
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| Skeletal and Stereochemical Diversification of Tricyclic Frameworks Inspired by Ca2+-ATPase Inhibitors, Artemisinin and Transtaganolide D.Oguri, H.; Yamagishi, Y.; Hiruma, T.; Oikawa, H. Org. Lett. 2009, 11, 601–604. |
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| Identification of Gene Cluster of Polyether Antibiotic Lasalocid from Streptomyces lasaliensis.Migita, A.; Watanabe, M.; Hirose, Y.; Watanabe, K.; Tokiwano, T.; Kinashi, H.; Oikawa, H. Biosci. Biotechnol. Biochem 2009, 73, 169-176. |