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1987 Fiscal Year Final Research Report Summary

Biosynthetic Studies of Natural Products and Their Application

Research Project

Project/Area Number 60303006
Research Category

Grant-in-Aid for Co-operative Research (A)

Allocation TypeSingle-year Grants
Research Field 天然物有機化学
Research InstitutionTOHOKU UNIVERSITY

Principal Investigator

OGURA Kyozo  Chemical Research Institute of Non-Aqueous Solutions, Tohoku University, 非水溶液化学研究所, 教授 (80006303)

Co-Investigator(Kenkyū-buntansha) SUGA Takayuki  Faculty of Science , Hiroshima University, 理学部, 教授 (00033811)
OHNO Atsuyoshi  Insitute for Chemical Research, Kyoto University, 化学研究所, 助教授 (70027077)
GOTO Toshio  Faculty of Agriculture, Nagoya University, 農学部, 教授 (20023369)
ITO Sho  Faculty of Science, Tohoku University, 理学部, 教授 (00004242)
MASAMUNE Tadashi  Faculty of Science, Hokkaido University, 理学部, 教授 (60000717)
Project Period (FY) 1985 – 1987
KeywordsNatural organic compounds / Natural product chemistry / Biosynthesis / Biosynthesis of isoprenoids / Phytoalexin / luciferase / 昆虫ホルモン
Research Abstract

(1) Metabolic pathways for rishitin, a phytoalexin of potato were clarified, and hydrogen peroxide was identified as an endogeneous elicitor of this phytoalexin. (2) The absolute stereochemistry of new prenyltransferase reactions were established. (3) Essential activation factors for undecaprenyl diphosphate synthase were isolated and identified. (4) The two essential protein components of hexaprenyl diphosphate synthase were purified and their functions were characterized. (5) Bacterial squalene synthetase was first isolated. (6) Phosphoryl derivatives of ecdysteroids were identified as conjugates in Bombyx ovaries. (7) Biosynthesis of ursolic acid from aceatate in tissue cultures of Rabdasia japonica Hara was elucidated with ^<13>C,^2H-double labeled precursors. (8) A complex consisting of luciferase and luciferin derived pigment was isolated from Cypridina. (9) Stereo- and regeo-controlled reactions with NAD(P)H models were developed. (10) Stereoselective reductions by yeast were used to prepare useful chiral synthons. (11) Acromelic acids, agelasines, and bayunol were synthesized by effective methods. (12) New terpenoids with novel strucures were isolated from marine organisms. (13) New synthetic reactions useful for biosynthetic study were developed.
Information was effectively exchanged among the members of this project to promote their research activities.

  • Research Products

    (112 results)

All Other

All Publications (112 results)

  • [Publications] K. Konno: Tetrahedrom Lett.27. 607-610 (1986)

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      「研究成果報告書概要(和文)」より
  • [Publications] K. Hashimoto: Chem. Lett.1399-1400 (1986)

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      「研究成果報告書概要(和文)」より
  • [Publications] M. Takasugi: J. Chem.Soc., Chem. Commun.621-622 (1985)

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      「研究成果報告書概要(和文)」より
  • [Publications] A. Murai: J. Chem. Soc., Chem. Commun.891-892 (1986)

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      「研究成果報告書概要(和文)」より
  • [Publications] A. Murai: Chem. Lett.771-772 (1986)

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      「研究成果報告書概要(和文)」より
  • [Publications] Y. Maki: Chem. Lett.1885-1888 (1986)

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      「研究成果報告書概要(和文)」より
  • [Publications] M. Kabayashi: J. Am. Chem. Soc.107. 4588-4589 (1985)

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      「研究成果報告書概要(和文)」より
  • [Publications] T. Koyama: J. Biochem.98. 449-456 (1985)

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      「研究成果報告書概要(和文)」より
  • [Publications] T. Koyama: J. Biochem.98. 457-463 (1985)

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      「研究成果報告書概要(和文)」より
  • [Publications] K. Ishii: Biochim. Biophys. Acta. 835. 291-297 (1985)

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      「研究成果報告書概要(和文)」より
  • [Publications] T. Koyama: Methods Enzymol.110. 153-155 (1985)

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  • [Publications] K. Ogura: Methods Enzymol. 110. 167-171 (1985)

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  • [Publications] H. Sagami: Methods Enzymol.110. 184-188 (1985)

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  • [Publications] H. Sagami: Methods Enzymol.110. 188-192 (1985)

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  • [Publications] H. Fujii: Methods Enzymol.110. 192-198 (1985)

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  • [Publications] I. Sagami: Methods Enzymol.110. 199-205 (1985)

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  • [Publications] H. Sagami: Methods Enzymol.110. 206-209 (1985)

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  • [Publications] I. Sagami: Methods Enzymol.110. 320-326 (1985)

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  • [Publications] M. Ito: Chem. Lett.101-104 (1986)

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  • [Publications] K. Isii: Biochem. J.233. 773-777 (1986)

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  • [Publications] G. Kusano: Chem.Pharm. Bull.34. 3465-3470 (1986)

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  • [Publications] M. Ishitsuka: Tetrahedron Lett.27. 2639-2642 (1986)

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  • [Publications] T. Kusumi: Chem.Lett.1241-1342 (1986)

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  • [Publications] M. Hirama: J. Org.Chem.50. 127-129 (1985)

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      「研究成果報告書概要(和文)」より
  • [Publications] M. Hirama: Tetrahedron Lett.26. 4133-4136 (1985)

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      「研究成果報告書概要(和文)」より
  • [Publications] M. Hirama: J. Am. Chem. Soc.107. 1797-1798 (1985)

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      「研究成果報告書概要(和文)」より
  • [Publications] M. Hirama: Tetrahedron Lett.26. 4137-4140 (1985)

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  • [Publications] M. Hirama: J. Chem. Soc.,Chem. Commun.393-394 (1986)

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  • [Publications] M. Kodama: Bull. Chem. Soc. Jpn.59. 1897-1900 (1986)

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  • [Publications] M. Hirama: Chem. Lett.1381-1384 (1986)

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  • [Publications] M. Hirama: Tetrahedron Lett.27. 5281-5284 (1986)

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  • [Publications] S. Seo: J. Chem. Soc., Chem. Commun.1139 (1986)

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  • [Publications] S. Seo: J. Chem. Soc., Chem. Commun.1141 (1986)

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  • [Publications] H. Otsuka: J. Biochem.99. 1339-1344 (1986)

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  • [Publications] S. Sakurai: Experientia. 42. 1034-1036 (1986)

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  • [Publications] D. Uemura: Tetrahedron. 41. 1007-1017 (1985)

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  • [Publications] Y. Toya: Tetrahedron Lett.26. 239-242 (1985)

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  • [Publications] H. Iio: J. Chem. Soc., Chem. Commun.774 (1985)

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  • [Publications] M. Nishizawa: Tetrahedron Lett.26. 1535-1536 (1985)

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  • [Publications] M. Nishizawa: J. Am. Chem. Soc.107. 522-523 (1985)

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  • [Publications] M. Nishizawa: J. Chem. Soc., Chem. Commun.395-396 (1985)

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  • [Publications] M. Nishizawa: J. Org. Chem.50. 5487-5490 (1985)

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  • [Publications] M. Nishizawa: Tetrahedron Lett.27. 187-190 (1986)

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  • [Publications] M. Nishizawa: J. Rg. Chem.51. 806-813 (1986)

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  • [Publications] M. Nishizawa: Tetrahedron Lett.27. 3255-3256 (1986)

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  • [Publications] M. Nishizawa: Chem. Pharm. Bull.34. 4443-4446 (1986)

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  • [Publications] Y. Yoshida: Biochem. Biophys. Res. Commun.127. 623-628 (1985)

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  • [Publications] T. Nishino: Methods Enzymol.110. 373-375 (1985)

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  • [Publications] Y. Yoshida: Developments in Biochemistry. 27. 439-442 (1985)

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  • [Publications] S. Fujisaki: J. Biochem.99. 1137-1146 (1986)

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  • [Publications] S. Fujisaki: J. Biochem.99. 1327-1337 (1986)

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  • [Publications] S. Yasui: J. Org. Chem.50. 3283 (1985)

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  • [Publications] A. Ohno: Tetrahedron. 42. 961 (1985)

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  • [Publications] K. Nakamura: Chem. Lett.87 (1986)

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  • [Publications] K. Ushio: Tetrahedron Lett.27. 2657 (1986)

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  • [Publications] A. Ohno: Bull. Chim. Soc. Jpn.59. 2905 (1986)

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  • [Publications] A. Ohno: J. Am. Chem. Soc.108. 6438 (1986)

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  • [Publications] T. Suga: J. Am. Chem. Soc.108. 2366-2371 (1986)

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  • [Publications] T. Suga: Phytochemistry. 25. 2769-2775 (1986)

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  • [Publications] T. Tabuchi: Tetrahedron Lett. 27. 1195-1196 (1986)

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  • [Publications] T. Tabuchi: Tetrahedron Lett.27. 5237-5240 (1986)

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  • [Publications] M. Takasugi, S. Okinaka, N. Katsui, T. Masamune, A. Shirata, M. Ohuchi: "Isolation and Structure of Letturcenin A, a Novel Guaianolide Phytoalexin from Lactuca sativa var. capitata (Compositae)" J. Chem. Soc., Chem. Commun.621-622 (1985)

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  • [Publications] A. Murai, Y. Yoshizawa, M. Ikura, N. Katsui, T. Masamune: "Metabolism of Rishitin. The NIH-like shift in Formation of Rishitin M-2" J. Chem. Soc., Chem. Commun.891-892 (1986)

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      「研究成果報告書概要(欧文)」より
  • [Publications] A. Murai, Y. Yoshizawa, N. Katsui, S. Sato, T. Masamune: "Oxysolavetivone. A New Niosynthetic Precursor of Lubimin in Potato" Chem. Lett.771-772 (1986)

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      「研究成果報告書概要(欧文)」より
  • [Publications] M. Takasugi, S. Kawashima, K. Monde, N. Katsui, T. Masamune, A. Shirata: "Antifungal Compounds from Dioscorea Batatas Inoculated with Pseudomonas Cichorii" Phytochemistry. 26. 371-375 (1987)

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  • [Publications] A. Murai, H. Miyazaki, K. Watanabe, T. Masamune: "An Efficient Synthesis of 15-Oxygenated T-Type Spirovetivanes. Its Application to the Synthesis of ( )-[8,8-^2H_2]Isolubimin" Chem. Lett.651-654 (1987)

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  • [Publications] A. Murai, Y. Yoshizawa, H. Miyazaki, T. Masamune, N. Sato: "Biosynthesis of Phytuberin" Chem. Lett.1377-1378 (1987)

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  • [Publications] K. Konno, K. Hashimoto, Y. Ohfune, H. Shirahama, T. Matsumoto: "Synthesis of Acromelic Acid A, a toxic Principle of Clitocybe acromelalga" Tetrahedron Lett.27. 607-610 (1986)

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  • [Publications] K. Hashimoto, K. Konno, H. Shirahama, T. Matsumoto: "Synthesis of Acromelic Acid B, a Toxic Principle of Clitocybe acromelalga" Chem. Lett.1399-1400 (1986)

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  • [Publications] K. Konno, K. Hashimoto, Y. Ohfune, H. Shirahama, T. Matsumoto: "Acromelic Acid A and B, Potent Neuroexcitatory Amino Acids Isolated from Clitocybe acromelalga" J. Am. Chem. Soc.

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  • [Publications] Y. Maki, G. Watanabe, A. Saito, T. Koyama, K. Ogura: "Unusual Farnesyl Pyrophosphate Synthetase Reacrion of an Artificial Substrate with Ni^<2+>" Chem. Lett.1885-1888 (1986)

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  • [Publications] H. Sagami, K. Ogura: "Nonaprenyl Pyrophosphate Synthetase from Micrococcus luteus" Methods in Enzymology. 110. 206-209 (1985)

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  • [Publications] I. Sagami, N. Ojima, K. Ogura, S. Seto: "Aspulvinone Dimethylallyltransferase" Mehtods in Enzymology. 110. 320-326 (1985)

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  • [Publications] M. Ito, T. Koyama, K. Ogura: "A Convenient Method of Stereochemical Analysis of Prenyltransferase Reaction and its Application" Chem. Lett.101-104 (1986)

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  • [Publications] Y. Maki, I. Shimada, H. Sugiyama: "The Stimulating Effectiveness of Optical Isomers of Glu-Val on the Labellar Sugr Receptor Site of the Flesh Fly" Peptide Chemistry. 1986. 241-246 (1987)

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  • [Publications] K. Ishii, H. Sagami, K. Ogura: "A Novel Prenyltransferase from Paracoccus denitrificans" Biochem. J.233. 773-777 (1986)

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  • [Publications] M. Kobayashi, M. Ito , T. Koyama, K. Ogura: "Stereochemistry of the Carbon to Carbon Bond Formation in the Biosynthesis of Polyprenyl Chains with Z Double Bonds. Studies with Undecaprenyl-Pyrophosphate Synthetase" J. Am. Chem. Soc.107. 4588-4589 (1985)

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  • [Publications] T. Koyama, M. Matsubara, K. Ogura: "Isoprenoid Enzyme Systems of Silkworm. I. Partial Purification of Isopentenyl Pyrophosphate Isomerase, Farnesyl Pyrophosphate Synthetase, and Geranylgeranyl Pyrophosphate Synthetase" J. Biochem.98. 449-456 (1985)

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  • [Publications] T. Koyama, M. Matsubara, K. Ogura: "Isoprenoid Enzyme Systems of Silkworm. II. Formation of the Juvenile Hormone Skeletons by Farnesyl Pyrophosphate Synthetase II" J. Biochem.98. 457-463 (1985)

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  • [Publications] K. Ishii, H. Sagami, K. Ogura: "Decaprenyl Pyrophosphate Synthetase from Paracoccus denitrificans" Biochim. Biophys. Acta. 835. 291-297 (1985)

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  • [Publications] T. Koyama, H. Fujii, K. Ogura: "Enzymatic Hydrolysis of Polyprenyl Pyrophosphates" Methods in Enzymology. 110. 153-155 (1985)

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  • [Publications] K. Ogura, T. Nishino, T. Shinka, S. Seto: "Prenyltransferases of Pumpkin Fruit" Methods in Enzymology. 110. 167-171 (1985)

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  • [Publications] H. Sagami, K. Ishii, K. Ogura: "Geranylgeranyl Pyrophospahte Synthetase of Pig Liver" Methods in Enzymology. 110. 184-188 (1985)

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  • [Publications] H. Sagami, K. Ogura: "Geranylpyrophosphate Synthetase-Geranylgeranylpyrophosphate Synthetase from Micrococcus luteus" Methods in Enzymology. 110. 188-192 (1985)

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  • [Publications] H. Fujii, T. Koyama, K. Ogura: "Hexaprenyl Pyrophosphate Synthetase of Micrococcus luteus B-P 26" Methods in Enzymology. 110. 192-198 (1985)

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  • [Publications] I. Sagami, H. Fujii, T. Koyama, K. Ogura: "Heptaprenyl Pyrophosphate Synthetase from Bacillus Subtilis" Methods in Enzymology. 110. 199-205 (1985)

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  • [Publications] T. Koyama, K. Ogura: "Synthesis and Absolute Configuration of 4-Methyl Juvenile Hormone I (4-MeJH I) by a Biogenetic Approach: A Combination of Enzymatic Synthesis ad Biotrans-formation" J. Am. Chem. Soc.109. 2853-2854 (1987)

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  • [Publications] M. Ito, M. Kobayashi, T. Koyama, K. Ogura: "Stereochemical Analysis of Prenyltransferase Reaction Leading to (Z)- and(E)- Polyprenyl Chains" Biochemistry. 26. 4745-4750 (1987)

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  • [Publications] T. Gotoh, T. Koyama, K. Ogura: "The Significance of the Diphosphate Linkage Involved in the Substrates for Prenyltransferase. Geranyl and Dimethylallyl Methylenediphosphate as Artificial Substrates" Chem. Lett.1627-1630 (1987)

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  • [Publications] I. Yoshida, T. Koyama, K. Ogura: "Dynamic Interaction between Components Hexaprenyl Diphosphte Synthase from Micrococcus luteus BP-26" Biochemistry. 26. 6840-6845 (1987)

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  • [Publications] T. Koyama, Y. Kokubun, K. Ogura: "Polyprenyl Diphosphate Synthase from Mulberry Leaves: Stereochemistry of Hydrogen Elimination in the Prenyltransferase Reaction" Phytochemistry.

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  • [Publications] T. Koyama, I. Yoshida, K.Ogura: "Undecaprenyl Diphosphate Synthase from Micrococcus luteus B-P 26 --- Essential Factors for the Enzymatic Activity" J. Biochem.(1988)

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  • [Publications] G. Kusano, Y. Koike, H. Inoue, S. Nozoe: "The Constituents of Gymnopilus spectabilis" Chem. Pharm. Bull.34. 3465-3470 (1986)

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  • [Publications] S. Nozoe, T. Ohta, N. Tabei, Y. Koike, G. Kusano: "Stereochemistry of Glutamate Ester Moiety of Gymnopilin" Chem. Pharm. Bull.

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  • [Publications] M. Hirama, T. Noda, S. Ito: "Convenient Synthesis of (S)-Citronellol of High Optical Purity" J. Org. Chem.50. 127-129 (1985)

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  • [Publications] M. Hirama, T. Sigemoto, S. Ito: "Intramolecular Michael Addition of O-Carbamates to , -Unsaturated Esters. A New Diastereoselective Amination in an Acyclic System" J. Am. Chem. Soc.107. 1797-1798 (1985)

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  • [Publications] M. Hirama, T. Sigemoto, Y. Yamazaki, S. Ito: "Diastereoselective Synthesis of N-Acetyl-D,L-acosamine and N-Benzoyl-D,L-ristosamine" Tetrahedron Lett.26. 4133-4136 (1985)

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  • [Publications] M. Hirama, T. Shigemoto. S. Ito: "Reversal of Diastereofacial Selectivity in the Intramolecular Micheal Addition of -Carbamoyloxy- , -unsaturated Esters. Synthesis of N-Benzoyl-D,L-daunosamine" Tetrahedron Lett.26. 4137-4140 (1985)

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  • [Publications] M. Hirama, I. Nishizaki, T. Shigemoto, S. Ito: "New Acyclic Approach to 3-Amino-2,3,6-trideoxy-L-hexoses: A Stereocontrolled Synthesis of N-Benzoyl L-Daunosamine" J. Chem. Soc., Chem. Commun.393-394 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M. Kodama, U. S. F. Tambunan, T. Tsunoda, S. Ito: "Total Sythesis of (-)-Vitrenal and its Biological Activity" Bull. Chem. Soc. Jpn.59. 1897-1900 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M. Hirama, T. Nakamine, S. Ito: "Trifunctional Chiral Synthons via Stereocontrolled Yeast Reduction. Preparation of Chiral Pentane-1,3,5-tiol Derivatives" Chem. Lett.1381-1384 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M. Hirama, T. Nakamine, S. Ito: "Enantiospecific Synthesis of the Spiroacetal Unit of Avermectin B_<la>" Tetrahedron Lett.27. 5281-5284 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S. Lilitokarntakul, M. Hirama, S. Ito: "Diastereoselective Deoxymercuration in Acyclic System. A Remarkable Assistance by the Neighboring Carbonate Group" Tetrahedron Lett.28. 1207-1210 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Tsunoda, M. Amaike, U. S. F. Tambunan, Y. Fujise, S. Ito, M. Kodama: "Total Synthesis of (+)-Lauren-1-ene. The Unique Fenestrane Diterpene" Tetrahedron Lett.28. 2537-2540 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M. Hirama, T. Shigemoto, S. Ito: "Stereodivergent Total Synthesis of N-Acetylacosamine and N-Benzoylristosamine" J. Org. Chem.52. 3342-3346 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M. Hirama, T. Iwakuma, S. Ito: "Diastereofacial Selectivity in the Intra-molecular Conjugate Addition of aNitrogen Nucleophile; Stereocontrolled Piperidine Synthesis" J. Chem. Soc., Chem. Commun.1523-1524 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M. Hirama, T. Noda, S. Ito, C.Kabuto: "Stereocontrolled Construction of the Hexahydrobenzofuran Subunit of the Avermectins and the Milbemycins: The Aldol Strategy" J. Org. Chem.53. 706-708 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M. Ishitsuka, T. Kusumi, H. Kakisawa: "Structural Elucidation and Conformational Analysis of Germacrane Type Diterpenoids from the Brown Alga Pachydictyon coriaceum" Tetrahedron Lett.27. 2639-2642 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Kusumi, D. Muanza Nkongolo, M. Ishitsuka, Y. Inouye, H. Kakisawa: "Structurel and Absolute Configuration of Isodictytriol, a New Diterpene from the Browm Alga Dictyota dichotoma" Chem. Lett.1241-1242 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Inouye, H. Uchida, T. Kusumi, H. Kakisawa: "Structure and Absolute Configuration of Aplysiapyranoid B, a New Polyhalogenated pyranoid Monoterpene from Aplysia kurodai" J.Chem. Soc., Chem. Commun.346-347 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Kusumi, I. Ohtani, K. Nishiyama, H. Kakisawa: "Caryoynencins, Potent Antibiotics from a Plant Pathogen Pseudomonas carophylli" Tetrahedron Lett.34. 3981-3984 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Goto: Recent Advances in the Chemistry of Cypridina Bioluminescence in "New Synthetic Methodology and Functionally Interesting Compounds". Kodansha, 285-306 (1986)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1989-03-30  

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