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1998 Fiscal Year Final Research Report Summary

Synthetic Studies on Optically Active Substances with Remarkable Bioactivities to Analyze Their Biological Functions

Research Project

Project/Area Number 09460056
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionThe University of Tokyo

Principal Investigator

KITAHARA Takeshi  The University of Tokyo, Graduate School of Agricultural and life Sciences, Professor, 大学院・農学生命科学研究科, 教授 (40087573)

Co-Investigator(Kenkyū-buntansha) WATANABE Hidenori  The University of Tokyo, Graduate School of Agricultural and life Sciences, Asso, 大学院・農学生命科学研究科, 助教授 (00202416)
Project Period (FY) 1997 – 1998
KeywordsBioactive molecules / Optically active substances / Structure-Activity-Relation / Inhibitor of cell progression / Insect antifeedant / Plant growth regulators / Biotinylated probes / Enzyme inhibitors
Research Abstract

1. Synthesis of radicicol, acetophthalidin and preussin, which show potent inhibition activities against cell-progression was studied. We could finish the synthesis not only of natural products but also related analogs including biotinylated derivatives. As a result, we found that some analogs of acetophthalidin have the similar activities and also all the possible 8 stereoisomers of preussin have the same activity at the similar level.
2. Synthesis of plant-growth regulators, such as jasmonoids, pironetin, specifernin, sorokinianin and so on was also accomplished and SAR studies were performed. In the case of pironetin, one of biotinylated analogs bound selectively with micro tubule and now the study on the analysis of function is underway.
3. Synthesis of natural products and analogs related to plant protection and plant nutrition. For example, insect antifeedant is a promising pesticide tolerant to eco-system. We succeeded in the synthesis of azadirachtin B-ring skeleton and also another antifeedant, tanabalin via very efficient scheme. These methodologies would be applied to synthesize related molecules to study their biological activities. Expeditious synthesis of phytosiderophores was developed and the synthesis of analogs was executed to create simpler but better derivatives.
4. Synthesis of pyrrolidine and piperidine analogs, such as nectrisine, DAB-1, LAB-1, nojirimycin and their analogs with potent glucosidase inhibitors was achieved.

  • Research Products

    (22 results)

All Other

All Publications (22 results)

  • [Publications] 北原武他3名: "Novel and Versatile Synthesis of Pyrrolidine Type Azasugars,DAB-1 and LAB-1,Potent Glucosidase Inhibitors." Tetrahedron. 53・22. 7501-7508 (1997)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 北原武他1名: "Synthesis of a Glycosidic Precursor of Isomeric Marmelo Oxides,Volatile Components of Quince Fruit,Cydonia oblonga." J.Nat.Prod.61・4. 551-554 (1998)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 北原武他4名: "Synthesis and Bioactivities of Acetophthalidin and Its Derivatives." Heterocycles. 48・10. 2049-2060 (1998)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 北原武他2名: "Synthesis of Both Enantiomers of Hybripyranone." Tetrahedron. 54・31. 8975-8984 (1998)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 北原武他2名: "Total Synthesis of(-)-Pironetin." Tetrahedron Lett.39・45. 8313-8316 (1998)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 北原武他1名: "Enantioselective Synthesis of Bioactive Molecules Related to Plant Protection and Physiology." J.Synth.Org.Chem.Jpn.56・11. 884-895 (1998)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hidenori Watanabe, Takeru Watanabe, Takeshi Kitahara and Kenji Mori: "Concise Synthesis of a Racemic and Diastereomeric Mixture of the Sex Pheromones of Matsucoccus Pine Scales" Biosci.Biotech.Biochem.61. 127-130 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yong Jip Kim, Masaru, Kido, Masahiko Bando and Takeshi Kitahara: "Novel and Versatile Synthesis of Pyrrolidine Type Azasugars, DAB-1 and LAB-1, Potent Glucosidase Inhibitors" Tetrahedron. 53. 7501-7508 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yong Jip Kim and Takeshi Kitahara: "Novel Synthesis of Nectrisine and 4-epi-Nectrisine" Tetrahedron Lett.38. 3423-3426 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hidenori Watanabe, Takeru Watanabe, Kenji Mori and Takeshi Kitahara: "Synthetic Study on Azadirachtin (Part 2) .Construction of the Decalin Moiety with Full Functionality on B-Ring" Tetrahedron Lett.38. 4429-4432 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yoshiharu Kinoshita and Takeshi Kitahara: "Total Synthesis of Phenazinomycin and Its Enantiomer via High-pressure Reaction" Tetrahedron Lett.38. 4993-4996 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hidenori Watanabe, Takahiro Onoda, Takeshi Kitahara and Kenji Mori: "Synthesis of (+) -Sorokinianin." Tetrahedron Lett.38. 6015-6018 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Takanobu Takeda, Hidenori Watanabe and Takeshi Kitahara: "Direct Oxidation of Acetals and Aldehydes to Esters." Synlett. 1149-1150 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hidenori Watanabe, Kanako Uchida and Takeshi Kitahara: "Synthesis of Both Enantiomers of Acetophthalidin." Heterocycles. 46. 45-48 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Takeshi Kitahara, Toru Hasegawa, Ken Ishigami and Yoshiharu Kinoshita: "Synthetic Studies on Antitumor Antibiotics and Enzyme Inhibitors." New Trends in Natural Product Chemistry, 1997, Atta-ru-Rahman ed., Harwood Academic Publishers, Amsterdam.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Sukbinder S.Klair, Mohan R.Hindupur and Takeshi Kitahara: "Novel Synthetic Approach Towards Phytosiderophores : Expeditious Synthesis of Nicotianamine and Deoxymugineic Acid" Tetrahedron Lett.39. 89-92 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Takeshi Kitahara and Hiroki Shimizu: "Synthesis of a Glycosidic Precursor of Isomeric Marmelo Oxides, Volatile Components of Quince Fruit, Cydonia oblonga" J.Nat.Prod.61. 551-554 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Kanako Uchida, Hidenori Watanabe, Takeo Usui, Hiroyuki Osada and Takeshi Kitahara: "Synthesis and Bioactivities of Acetophthalidin and Its Derivatives" Heterocycles. 48. 2049-2060 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Naoto Kogoshi, Akira Takatsuki, Yong Jip Kim and Takeshi Kitahara: "Synthesis of Unnatural Enantiomer of Nectrisine and Its Biological Activity" Heterocycles. 49. 63-66 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yoshitaka Matsushima, Takeshi Kitahara and Kenji Mori: "Lipase-catalyzed Kinetic Resolution of * -cis, cis-Spiro [4.4] nonane-1,6-diol." Biosci.Biotech.Biochem.62. 1435-1437 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Kanako Uchida, Hidenori Watanabe and Takeshi Kitahara: "Synthesis of Both Enantiomers of Hybripyranone." Tetrahedron. 54. 8975-8984 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hiroyuki Watanabe, Hidenori Watanabe and Takeshi Kitahara: "Total Synthesis of (-) -Pironetin." Tetrahedron Lett.39. 8313-8316 (1998)

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

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Published: 1999-12-08  

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