publication2010(english) of Lab. of Synthetic Bioorganic Chemistry

2010年
A new sesquiterpenoid produced by famale Callosobruchus rhodesianus (Pic): a possible component of the sex attractant pheromoneShimomura, K.; Koshino, H.; Yajima, A.; Matsumoto, N.; Yajima, S.; Ohsawa, K.Tetrahedron Lett. 2010, 51, 6860-6862.doi:10.1016/j.tetlet.2010.10.100
Synthesis of (2RS,8R,10R)-YM-193221 and an Improved Approach to Tyroscherin, Bioactive Natural Compounds from Pseudallescheria sp.Katsuta, R.; Yajima, A.; Ishigami, K.; Nukada, T.; Watanabe, H.Biosci. Biotechnol. Biochem.2010,74, 2056-2059.doi:10.1271/bbb.100361
Contact Sex Pheromone Components of the Seed Beetle, Callosobruchus analis (F.)Shimomura, K.; Akasaka, K.; Yajima, A.; Mimura, T.; Yajima, S.; Ohsawa, K.J. Chem. Ecol. 2010, 36, 955-965.doi:10.1007/s10886-010-9841-z
Comparison of components and synthesis genes of cell wall teichoic acid among Lactobacillus plantarum strainsTomita, S.; Irisawa, T.; Tanaka, N.; Nukada, T.; Satoh, E.; Uchimura, T.; Okada, S.Biosci. Biotechnol. Biochem. 2010, 74, 928-933.doi:10.1271/bbb.90736
2,3-Dihydrohomofarnesal: Female sex attractant pheromone component of Callosobruchus rhodesianus (Pic)Shimomura, K.; Koshino, H.; Yajima, A.; Matsumoto, N.; Kagohara, Y.; Kamada, K.; Yajima, S.; Ohsawa, K.J. Chem. Ecol. 2010, 36, 824-833.doi:10.1007/s10886-010-9824-0
Synthesis of a proposed structure for the diffusible extracellular factor of Xanthomonas campestris pv. campestrisYajima, A.; Imai, N.; Poplawsky, A. R.; Nukada, T.; Yabuta, G.Tetrahedron Lett. 2010, 51, 2074-2077.doi:10.1016/j.tetlet.2010.02.088
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2009年
Structures of two monomeric units of teichoic acid prepared from the cell wall of Lactobacillus plantarum NRIC 1068Tomita, S.; Furihata, K.; Nukada, T.; Satoh, E.; Uchimura, T.; Okada, S.Biosci. Biotechnol. Biochem. 2009, 73, 530-535.doi:10.1271/bbb.80582
Flavonoids in Sasa senanensis and their antioxidative activitiesMatsuda, T.; Yamazaki, M.; Yajima, A.; Tomidzuka, N.; Nishizawa, M.Food Preservation Science 2009, 35, 11-16.
A simple synthesis of four stereoisomers of roseoside and their inhibitory activity on leukotriene release from mice bone marrow-derived cultured mast cellsYajima, A.; Oono, Y.; Nakagawa, R.; Nukada, T.; Yabuta, G.Bioorg. Med. Chem. 2009, 17, 189-194.doi: 10.1016/j.bmc.2008.11.002
Synthesis and structure revision of tyroscherin, and bioactivities of its stereoisomers against IGF-1-dependent tumor cells.Ishigami, K.; Katsuta, R.; Shibata, C.; Hayakawa, Y.: Watanabe, H.; Kitahara, T.Tetrahedron 2009, 65, 3629-3638.doi:10.1016/j.tet.2009.03.003
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2008年
Synthesis and stereochemistry-activity relationship of small bacteriocin, an autoinducer of the symbiotic nitrogen-fixing bacterium Rhizobium leguminosarumYajima, A.; van Brussel, A. A. N.; Schripsema, J.; Nukada, T.; Yabuta, G.Org. Lett. 2008, 10, 2047-2050.doi: 10.1021/ol8005198
Synthesis and absolute configuration of hormone alpha1Yajima, A.; Qin, Y.; Zhou, Z.; Kawanishi, N.; Xiao, X.; Wang, J.; Zhang, D.; Wu, Y.; Nukada, T.; Yabuta, G.; Qi, J.; Asano, T.; Sakagami, Y.Nat. Chem. Biol. 2008, 4, 235-237.doi: 10.1038/nchembio.74
Synthesis and structure revision of tyroscherin, a growth inhibitor of IGF-1-dependent tumor cells.Katsuta, R.; Shibata, C.; Ishigami, K.; Watanabe, H.; Kitahara, T.Tetrahedron Lett. 2008, 49, 7042-7045.doi:10.1016/j.tetlet.2008.09.141
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2007年
DFT studies of the role of C-2-O-2 bond rotation in neighboring-group glycosylation reactions.Whitfield, D. M.; Nukada, T.Carbohyd. Res. 2007, 342, 1291-1304.doi:10.1016/j.carres.2007.03.030
Asymmetric total synthesis of ent-sandaracopimaradiene, a biosynthetic intermediate of oryzalexinsYajima, A.; Yamaguchi, A.; Nukada, T.; Yabuta, G.Biosci. Biotechnol. Biochem. 2007, 71, 2822-2829.doi:10.1271/bbb.70468
Efficient and stereo-selective syntheses of three stereoisomers of the sex pheromone of the cowpea Weevil, Callosobruchus maculatusYajima, A.; Yamamoto, M.; Nukada, T.; Yabuta, G.Biosci. Biotechnol. Biochem. 2007, 71, 2720-2724.doi:10.1271/bbb.70309
Direct determination of the stereoisomeric composition of callosobruchusic acid, the copulation release pheromone of the azuki bean weevil, Callosobruchus chinensis L., by the 2D-Ohrui-Akasaka method.Yajima, A.; Akasaka, K.; Yamamoto, M.; Ohmori, S.; Nukada, T.; Yabuta, G.J. Chem. Ecol. 2007, 33, 1328-1335.doi: 10.1007/s10886-007-9311-4
Synthesis and biological activity of a stereoisomeric mixture of the mating horomone of PhytophthoraYajima, A.; Kawanishi, N.; Qi, J.; Asano, T.; Sakagami, Y.; Nukada, T.; Yabuta, G.Tetrahedron Lett. 2007, 48, 4601-4603.doi:10.1016/j.tetlet.2007.04.109
Determination of the absoluteconfiguration of the biologically active natural product by Ohrui-Akasaka methodYajima, A.J. Synth. Org. Chem. Jpn. 2007, 65, 226-227.J-STAGE
Asymmetric synthesis of abietane diterpenoids via B-alkyl Suzuki-Miyaura coupling. Formal total asymmetric synthesis of 12-deoxyroyleanone and cryptoquinoneYajima, A.; Yamaguchi, A.; Saitou, F.; Nukada, T.; Yabuta, G.Tetrahedron 2007, 63, 1080-1084.doi:10.1016/j.tet.2006.11.072
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2006年
Investigations into the role of oxacarbenium ions in glycosylation reactions by ab initio molecular dynamics.Ionescu, A. R.; Whitfield, D. M.; Zgierski, M. Z.; Nukada, T.Carbohyd. Res. 2006, 341, 2912-2920.doi:10.1016/j.carres.2006.09.027
Two Unexpected Effects Found with 2,3,4,6-Tatra-O-methyl-D-Gluco- and Mannopyranosyl Oxacarbenium Ions. An O-2 Pseudoequatorial and a Large H-2-C-2-O-2-CH3 syn Preferencelonescu, A.; Wang, L.; Zgierski, M. Z.; Nukada, T.; Whitfield, D. M.ACS Symposium Series 2006, 930, 302-319.doi: 10.1021/bk-2006-0930
Practical Application of Computational Studies of the Glycosylation ReactionWhitfield, D. M.; Nukada, T.ACS Symposium Series 2006, 932, 265-300.doi: 10.1021/bk-2006-0932
Preparation of heat-stable antioxidant luteolin 6-C-glucoside (isoorientin) from Sasa or bamboo leavesYamazaki, M.; Matsuda, T.; Yajima, A.Jpn. Kokai Tokkyo Koho (2006), JP 2006265250
Novel flavonoid compound, its manufacture, and antioxidants containing itYamazaki, M.; Matsuda, T.; Yajima, A.Jpn. Kokai Tokkyo Koho (2006), JP 2006265249
Manufacture of tricin from bamboo leavesYamazaki, M.; Matsuda, T.; Yajima, A.Jpn. Kokai Tokkyo Koho (2006), JP 2006265248
Manufacture of antioxidative composition containing flavonoids extracted from bamboo grass leaves or bamboo leavesYamazaki, M.; Matsuda, T.; Yajima, A.Jpn. Kokai Tokkyo Koho (2006), JP 2006265247
Direct determination of the stereoisomer constitution by 2D-HPLC and stereochemistry-pheromone activity relationship of the copulation release pheromone of the cowpea weevil, Callosobruchus maculatusYajima, A.; Akasaka, K.; Nakai, T.; Maehara, H.; Nukada, T.; Ohrui, H.; Yabuta, G.Tetrahedron 2006, 62, 4590-4596.doi:10.1016/j.tet.2006.02.059
Stereoselective synthesis of Sch 642305, an inhibitor of bacterial DNA primaseIshigami, K.; Katsuta, R.; Watanabe, H.Tetrahedron 2006, 62, 2224-2230.doi:10.1016/j.tet.2005.12.009
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2005年
Conformational Pathways of Saturated Six-Membered Rings. A Static and Dynamical Density Functional Study.Ionescu, A. R.; Berces, A.; Zgierski, M. Z.; Whitfield, D. M.; Nukada, T.J. Phys. Chem. A 2005, 109, 8096-8105.doi:10.1021/jp052197t
The two-conformer hypothesis: 2,3,4,6-tetra-O-methyl-mannopyranosyl and -glucopyranosyl oxacarbenium ionsNukada, T.; Berces, A.; Wang, L.; Zgierski, M. Z.; Whitfield, D. M.Carbohyd. Res. 2005, 340, 841-852.doi:10.1016/j.carres.2004.12.021
Synthesis of the four stereoisomers of 2,6-dimethyloctane-1,8-dioic acid, a component of the copulation release pheromone of the cowpea weevil, Callosobruchus maculatusNakai, T.; Yajima, A.; Akasaka, K.; Kaihoku, T.; Ohtaki, M.; Nukada, T.; Ohrui, H.; Yabuta, G.Biosci. Biotechnol. Biochem. 2005, 69, 2401-2408.doi:10.1271/bbb.69.2401
Synthesis of cordiaquinone J and K via B-alkyl Suzuki-Miyaura coupling as a key step and determination of the absolute configuration of natural productsYajima, A.; Saitou, F.; Sekimoto, M.; Maetoko, S.; Nukada, T.; Yabuta, G.Tetrahedron 2005, 61, 9164-9172.doi:10.1016/j.tet.2005.06.115
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2004年
糖ピラノース環状配座の化学的直観に基づいた表現方法額田恭郎日本化学会情報化学部会誌 2004, 22, 116-117.JOI JST.JSTAGE/cicsj/22.116
Is acyl migration to the aglycon avoidable in 2-acyl assisted glycosylation reactions?Berces, A.; Whitfield, D. M.; Nukada, T.; do Santos Z., I.; Obuchowska, A.; Krepinsky, J. J.Can. J. Chem. 2004, 82, 1157-1171.doi:10.1139/V04-059
Immobilized Baker's yeast reduction in fluorous mediaYajima, A.; Naka, K.; Yabuta, G.Tetrahedron Lett. 2004, 45, 4577-4579.doi:10.1016/j.tetlet.2004.03.172
Molecular cloning and characterization of a cDNA encoding ent-cassa-12,15-diene synthase, a putative diterpenoid phytoalexin biosynthetic enzyme, from suspension-cultured rice cells treated with a chitin elicitor.Cho, E.-M.; Okada, A.; Kenmoku, H.; Otomo, K.; Toyomasu, T.; Mitsuhashi, W.; Sassa, T.; Yajima, A.; Yabuta, G.; Mori, K.; Oikawa, H.; Toshima, H.; Shibuya, N.; Nojiri, H.; Omori, T.; Nishiyama, M.; Yamane, H.Plant J. 2004, 37, 1-8.doi:10.1046/j.1365-313X.2003.01926.x
Total synthesis of ent-cassa-12,15-diene, a putative precursor of rice phytoalexins, phytocassanes A-E.Yajima, A.; Mori, K.; Yabuta, G.Tetrahedron Lett. 2004, 45, 167-169.doi:10.1016/j.tetlet.2003.10.131
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2003年
Synthesis and absolute configuration of cordiaquinone K, antifungal and larvicidal meroterpenoid isolated from the Panamanian plant, Cordia curassavica.Yajima, A.; Saitou, F.; Sekimoto, M.; Maetoko, S.; Yabuta, G.Tetrahedron Lett. 2003, 44, 6915-6918.doi:10.1016/S0040-4039(03)01669-1
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2002年
Can the stereochemical outcome of glycosylation reactions be controlled by the conformational preferences of the glycosyl donor?Nukada, T.; Berces, A.; Whitfield, D. M.Carbohyd. Res. 2002, 337, 765-774.doi:10.1016/S0008-6215(02)00043-5
Lucilianosides A and B, two novel tetranor-lanostane hexaglycosides from the bulbs of Chionodoxa luciliae.Kuroda, M.; Mimaki, Y.; Ori, K.; Koshino, H.; Nukada, T.; Sakagami, H.; Sashida, Y.Tetrahedron 2002, 58, 6735-6740.doi:10.1016/S0040-4020(02)00672-5
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2001年
The Conformational Origin of the Barrier to the Formation of Neighboring Group Assistance in Glycosylation Reactions: A Dynamical Density Functional Theory Study.Berces, A.; Enright, G.; Nukada, T.; Whitfield, D. M.J. Am. Chem. Soc. 2001, 123, 5460-5464.doi:10.1021/ja001194l
Quantitative description of six-membered ring conformations following the IUPAC conformational nomenclature.Berces, A.; Whitfield, D. M.; Nukada, T.Tetrahedron 2001, 57, 477-491.doi:10.1016/S0040-4020(00)01019-X
Synthesis and absolute configuration of MQ-A3 [1-(14'-methylhexadecanoyl)pyrrolidine], a novel aliphatic pyrrolidine amide from the tropical Convolvulaceous species.Yajima, A.; Yabuta, G.Biosci. Biotechnol. Biochem. 2001, 65, 463-465.doi:10.1271/bbb.65.463
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