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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
Project Status Completed (Fiscal Year 1987)
Budget Amount *help
¥7,700,000 (Direct Cost: ¥7,700,000)
Fiscal Year 1987: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1986: ¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1985: ¥4,500,000 (Direct Cost: ¥4,500,000)
KeywordsNatural organic compounds / Natural product chemistry / Biosynthesis / Biosynthesis of isoprenoids / Phytoalexin / luciferase / 昆虫ホルモン / 微生物還元 / 代謝物 / 立体化学 / イソプレノイド / 立体特異性
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.

Report

(2 results)
  • 1987 Final Research Report Summary
  • 1986 Annual Research Report
  • Research Products

    (150 results)

All Other

All Publications (150 results)

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

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K. Hashimoto: Chem. Lett.1399-1400 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Takasugi: J. Chem.Soc., Chem. Commun.621-622 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] A. Murai: J. Chem. Soc., Chem. Commun.891-892 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] A. Murai: Chem. Lett.771-772 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Y. Maki: Chem. Lett.1885-1888 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Kabayashi: J. Am. Chem. Soc.107. 4588-4589 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] T. Koyama: J. Biochem.98. 449-456 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] T. Koyama: J. Biochem.98. 457-463 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K. Ishii: Biochim. Biophys. Acta. 835. 291-297 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] T. Koyama: Methods Enzymol.110. 153-155 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K. Ogura: Methods Enzymol. 110. 167-171 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] H. Sagami: Methods Enzymol.110. 184-188 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] H. Sagami: Methods Enzymol.110. 188-192 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] H. Fujii: Methods Enzymol.110. 192-198 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] I. Sagami: Methods Enzymol.110. 199-205 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] H. Sagami: Methods Enzymol.110. 206-209 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] I. Sagami: Methods Enzymol.110. 320-326 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Ito: Chem. Lett.101-104 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K. Isii: Biochem. J.233. 773-777 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] G. Kusano: Chem.Pharm. Bull.34. 3465-3470 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Ishitsuka: Tetrahedron Lett.27. 2639-2642 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] T. Kusumi: Chem.Lett.1241-1342 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Hirama: J. Org.Chem.50. 127-129 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Hirama: Tetrahedron Lett.26. 4133-4136 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Hirama: J. Am. Chem. Soc.107. 1797-1798 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Hirama: Tetrahedron Lett.26. 4137-4140 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Hirama: J. Chem. Soc.,Chem. Commun.393-394 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Kodama: Bull. Chem. Soc. Jpn.59. 1897-1900 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Hirama: Chem. Lett.1381-1384 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Hirama: Tetrahedron Lett.27. 5281-5284 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] S. Seo: J. Chem. Soc., Chem. Commun.1139 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] S. Seo: J. Chem. Soc., Chem. Commun.1141 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] H. Otsuka: J. Biochem.99. 1339-1344 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] S. Sakurai: Experientia. 42. 1034-1036 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] D. Uemura: Tetrahedron. 41. 1007-1017 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Y. Toya: Tetrahedron Lett.26. 239-242 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] H. Iio: J. Chem. Soc., Chem. Commun.774 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Nishizawa: Tetrahedron Lett.26. 1535-1536 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Nishizawa: J. Am. Chem. Soc.107. 522-523 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Nishizawa: J. Chem. Soc., Chem. Commun.395-396 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Nishizawa: J. Org. Chem.50. 5487-5490 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Nishizawa: Tetrahedron Lett.27. 187-190 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Nishizawa: J. Rg. Chem.51. 806-813 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Nishizawa: Tetrahedron Lett.27. 3255-3256 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Nishizawa: Chem. Pharm. Bull.34. 4443-4446 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Y. Yoshida: Biochem. Biophys. Res. Commun.127. 623-628 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] T. Nishino: Methods Enzymol.110. 373-375 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Y. Yoshida: Developments in Biochemistry. 27. 439-442 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] S. Fujisaki: J. Biochem.99. 1137-1146 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] S. Fujisaki: J. Biochem.99. 1327-1337 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] S. Yasui: J. Org. Chem.50. 3283 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] A. Ohno: Tetrahedron. 42. 961 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K. Nakamura: Chem. Lett.87 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K. Ushio: Tetrahedron Lett.27. 2657 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] A. Ohno: Bull. Chim. Soc. Jpn.59. 2905 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] A. Ohno: J. Am. Chem. Soc.108. 6438 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] T. Suga: J. Am. Chem. Soc.108. 2366-2371 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] T. Suga: Phytochemistry. 25. 2769-2775 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] T. Tabuchi: Tetrahedron Lett. 27. 1195-1196 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] T. Tabuchi: Tetrahedron Lett.27. 5237-5240 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [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)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [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)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [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)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [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)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [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)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] A. Murai, Y. Yoshizawa, H. Miyazaki, T. Masamune, N. Sato: "Biosynthesis of Phytuberin" Chem. Lett.1377-1378 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [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)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [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)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [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.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [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)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] H. Sagami, K. Ogura: "Nonaprenyl Pyrophosphate Synthetase from Micrococcus luteus" Methods in Enzymology. 110. 206-209 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] I. Sagami, N. Ojima, K. Ogura, S. Seto: "Aspulvinone Dimethylallyltransferase" Mehtods in Enzymology. 110. 320-326 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Ito, T. Koyama, K. Ogura: "A Convenient Method of Stereochemical Analysis of Prenyltransferase Reaction and its Application" Chem. Lett.101-104 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [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)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K. Ishii, H. Sagami, K. Ogura: "A Novel Prenyltransferase from Paracoccus denitrificans" Biochem. J.233. 773-777 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [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)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [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)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [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)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K. Ishii, H. Sagami, K. Ogura: "Decaprenyl Pyrophosphate Synthetase from Paracoccus denitrificans" Biochim. Biophys. Acta. 835. 291-297 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] T. Koyama, H. Fujii, K. Ogura: "Enzymatic Hydrolysis of Polyprenyl Pyrophosphates" Methods in Enzymology. 110. 153-155 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K. Ogura, T. Nishino, T. Shinka, S. Seto: "Prenyltransferases of Pumpkin Fruit" Methods in Enzymology. 110. 167-171 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] H. Sagami, K. Ishii, K. Ogura: "Geranylgeranyl Pyrophospahte Synthetase of Pig Liver" Methods in Enzymology. 110. 184-188 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] H. Sagami, K. Ogura: "Geranylpyrophosphate Synthetase-Geranylgeranylpyrophosphate Synthetase from Micrococcus luteus" Methods in Enzymology. 110. 188-192 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] H. Fujii, T. Koyama, K. Ogura: "Hexaprenyl Pyrophosphate Synthetase of Micrococcus luteus B-P 26" Methods in Enzymology. 110. 192-198 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [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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      「研究成果報告書概要(欧文)」より
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      1987 Final Research Report Summary
  • [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)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [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)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [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)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] I. Yoshida, T. Koyama, K. Ogura: "Dynamic Interaction between Components Hexaprenyl Diphosphte Synthase from Micrococcus luteus BP-26" Biochemistry. 26. 6840-6845 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] T. Koyama, Y. Kokubun, K. Ogura: "Polyprenyl Diphosphate Synthase from Mulberry Leaves: Stereochemistry of Hydrogen Elimination in the Prenyltransferase Reaction" Phytochemistry.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [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)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] G. Kusano, Y. Koike, H. Inoue, S. Nozoe: "The Constituents of Gymnopilus spectabilis" Chem. Pharm. Bull.34. 3465-3470 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] S. Nozoe, T. Ohta, N. Tabei, Y. Koike, G. Kusano: "Stereochemistry of Glutamate Ester Moiety of Gymnopilin" Chem. Pharm. Bull.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Hirama, T. Noda, S. Ito: "Convenient Synthesis of (S)-Citronellol of High Optical Purity" J. Org. Chem.50. 127-129 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [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)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [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)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [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)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [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
    • Related Report
      1987 Final Research Report Summary
  • [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
    • Related Report
      1987 Final Research Report Summary
  • [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
    • Related Report
      1987 Final Research Report Summary
  • [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
    • Related Report
      1987 Final Research Report Summary
  • [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
    • Related Report
      1987 Final Research Report Summary
  • [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
    • Related Report
      1987 Final Research Report Summary
  • [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
    • Related Report
      1987 Final Research Report Summary
  • [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
    • Related Report
      1987 Final Research Report Summary
  • [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
    • Related Report
      1987 Final Research Report Summary
  • [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
    • Related Report
      1987 Final Research Report Summary
  • [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
    • Related Report
      1987 Final Research Report Summary
  • [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
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      1987 Final Research Report Summary
  • [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
    • Related Report
      1987 Final Research Report Summary
  • [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
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Koichi Ishii: Biochemical Journal. 233. 773-777 (1986)

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      1986 Annual Research Report
  • [Publications] Michio Ito: Chemistry Letters. 101-104 (1986)

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      1986 Annual Research Report
  • [Publications] Yuji Maki: Chemistry Letters. 1885-1888 (1986)

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      1986 Annual Research Report
  • [Publications] Masahiro Hirama: Journal of the Chemical Society,Chemical Communications. ission. 393-394 (1986)

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      1986 Annual Research Report
  • [Publications] Masahiro Hirama: Chemistry Letters. 1381-1384 (1986)

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      1986 Annual Research Report
  • [Publications] Masahiro Hirama: Tetrahedron Letters. 27. 5281-5284 (1986)

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      1986 Annual Research Report
  • [Publications] K.Konno: Tetrahedron Letters. 27. 3865-3868 (1986)

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      1986 Annual Research Report
  • [Publications] K.Konno: Heterocycles. 24. 2169 (1986)

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      1986 Annual Research Report
  • [Publications] K.Hashimoto: Chemistry Letters. 1399-1400 (1986)

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      1986 Annual Research Report
  • [Publications] T.Okuno: Agricaltural Biological Chemistry. 50. 997 (1986)

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      1986 Annual Research Report
  • [Publications] K.Konno: Tetrahedron Letters. 27. 607-610 (1986)

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      1986 Annual Research Report
  • [Publications] T.Kusumi: Chemistry Letters. 1241-1242 (1986)

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      1986 Annual Research Report
  • [Publications] M.Ishitsuka: Tetrahedron Letters. 23. 1241-1242 (1986)

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      1986 Annual Research Report
  • [Publications] S.Inouye: Biochemistry. 25. 8425-8429 (1986)

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      1986 Annual Research Report
  • [Publications] F.I.Tsuji: Proceedings of National Academy of Science,U.S.A.83. 8107-8111 (1986)

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      1986 Annual Research Report
  • [Publications] H.Otsuka: The Journal of Biochemistry. 99. 1339-1334 (1986)

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      1986 Annual Research Report
  • [Publications] M.Nishizawa: The Journal of Organic Chemistry. 51. 806-813 (1986)

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      1986 Annual Research Report
  • [Publications] M.Nishizawa: Tetrahedron Letters. 27. 187-190 (1986)

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      1986 Annual Research Report
  • [Publications] A.Ohno: Tetrahedron. 42. 961-973 (1986)

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      1986 Annual Research Report
  • [Publications] K.Nakmura: Chemistry Letters. 87-88 (1986)

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      1986 Annual Research Report
  • [Publications] K.Ushio: Tetrahedron Letters. 27. 2657-2660 (1986)

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      1986 Annual Research Report
  • [Publications] K.Nakamura: Tetrahedron Letters. 27. 3155-3156 (1986)

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      1986 Annual Research Report
  • [Publications] A.Ohno: Bulletin of the Chemical Society of Japan. 59. 2905-2906 (1986)

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      1986 Annual Research Report
  • [Publications] A.Ohno: Journal of the American Chemical Society. 108. 6438-6440 (1986)

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      1986 Annual Research Report
  • [Publications] Ikuo Nishida: The Journal of Biochemistry. 99. 1447-1454 (1986)

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      1986 Annual Research Report
  • [Publications] Akihiko Kawaguchi: The Journal of Biochemistry. 99. 1735-1742 (1986)

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      1986 Annual Research Report
  • [Publications] Atsuyoshi Ohno: Israel Journal of Chemistry. (1987)

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      1986 Annual Research Report
  • [Publications] Kaoru Nakamura: The Journal of Organic Chemistry. (1987)

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      1986 Annual Research Report
  • [Publications] Suchart Lilitkarntakul: Tetrahedron Letters. (1987)

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      1986 Annual Research Report
  • [Publications] Takayuki Suga: Chemistry Letters. 497-500 (1987)

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      1986 Annual Research Report
  • [Publications] Hideo Iio: Journal of the Chemical Society,Chemical Communications. (1987)

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      1986 Annual Research Report
  • [Publications] Michio Ito: Biochemistry. (1987)

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      1986 Annual Research Report
  • [Publications] Masahiro Hirama: The Journal of Organic Chemistry.

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      1986 Annual Research Report
  • [Publications] Tanetoshi Koyama: Journal of the American Chemical Society. under subm.

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      1986 Annual Research Report
  • [Publications] Takayuki Suga: Journal of the Chemical Society,Perkin Transaction.

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      1986 Annual Research Report
  • [Publications] Ichiro Yoshida: Biochemistry.

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      1986 Annual Research Report
  • [Publications] Yoshimasa Hirata: "Chemistry and Pharmacology of Palytoxin" Marcel Dekker, (1987)

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      1986 Annual Research Report
  • [Publications] Toshio Goto edited by Z.Yoshida: "New Synthetic Methodology and Functionally Interesting Compounds" Kodansha, 285-306 (1986)

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      1986 Annual Research Report

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Published: 1987-03-31   Modified: 2016-04-21  

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