Synthetic Studies of Gloeosporone, A Self-Inhibitor for Germination of Spores of Colletotrichum gloeosporioides
| Project/Area Number |
63570997
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | Nagasaki University |
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Principal Investigator |
IRIE Hiroshi Professor, Nagasaki Univ. Faculty of Pharmaceutical Scie., 薬学部, 教授 (00025686)
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| Co-Investigator(Kenkyū-buntansha) |
UENO Tamio Associate Prof. Kyoto Univ., Department of Agriculture, 農学部, 助教授 (20026579)
TAKEDA Shigeko Research Assistant, Nagasaki Univ. Faculty of Pharmaceutical Scie., 薬学部, 助手 (50039640)
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| Project Period (FY) |
1988 – 1989
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| Project Status |
Completed (Fiscal Year 1989)
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| Budget Amount *help |
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1989: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1988: ¥1,400,000 (Direct Cost: ¥1,400,000)
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| Keywords | Spores of Fungus / Self-inhibito / Gloeosporone / Carbamate formation / Resolution / 天然物全合成 / 植物病原菌 / さび菌胞子 / 立体異性体 / 光学活性体の合成 / 炭そ病菌 / 胞子自己発芽抑制因子 |
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| Research Abstract |
Some spores of plant pathogenic fungi possess the compounds, named as self-inhibitor, which interfere the germination of spores. In 1982, Mayor and his coworkers reported the isolation of a self-inhibitor, gloeosporone, from the fungus Colletotrichum gloeosporioide. We aimed at the synthesis of the compound to investigate the structure-activity relationship.
In the first year of the grant, we accomplished the synthesis of gloeosporone as a racemic modification along with its diastereoisomer. Based on the result, we focused on the synthesis of these compounds in optically active forms. Application of Lewis acid catalysed preparation of the carbamates on (dl)-1-tridecene-8-ol with (S)-1-(1-naphthyl)ethyl isocyanate (Pirkle's reagent) gave a mixture of the diastereoisomeric carbamates. After separation of each isomer in pure form, the optically active 1-decene-8-ols were regenerated by reduction with lithium aluminum hydride. By tracing the procedure for synthesis of racemic gloeosporone, the synthesis of (+)- and (-)-gloeosporone and their stereoisomers were completed. The biological test of these compounds synthesized, however, have the weak activity as a self-inhibitor. The effort to disclose the discrepancy between the reported data and our results is under investigation.
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Report
(3 results)
Research Products
(10 results)
