1995 Fiscal Year Final Research Report Summary
Asymmetric Synthesis of Optically Active Natural Products by Lipase-Catalyzed Hydrolysis in Organic Solvent System
| Project/Area Number |
06660139
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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 |
Bioproduction chemistry/Bioorganic chemistry
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| Research Institution | Okayama University of Science |
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Principal Investigator |
NAOSHIMA Yoshinobu Okayama University of Science, Fuaculty of Scuebcem Department of Biochemistry Professor, 理学部, 教授 (20113194)
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| Project Period (FY) |
1994 – 1995
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| Keywords | Biocatalyst / Lipase / Bioransformation / Enantioselectivity / Pheromone / Hydrolysis / Asymmetric Synthesis / Enzymatic Reaction |
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| Research Abstract |
1. We showed that lipase PS-catalyzed hydrolysis displays a higher enantioselectivity in an acetone-water system than in an aqueous system and that the biocatalytic system conyaining acetone could be successfully applied to the chiral synthesis of both the enantiomers of 3-octanol, the pheromone of various species of ants, of (S) 2-tridecanyl acetate and (S) -2-pentadecanyl acetate, the aggregation pheromone components of Drosophila mulleri and D.busckii, and of (R) patulolide A,a macrolide antibiotic isolated from Penicillium urticae S11R59.
2. We carried out the enzymatic hydrolysis of the acetates of aliphatic secondary alcohols with lipases PS,AK,and LIP.High enantioselectivity was observed for the lipase PS-catalyzed hydrolysis of (E) -allylic acetate and propargylic acetate in an acetone-water solvent system. In contrast, a decrease in enantio-selectivity was observed for (E) -homoallylic acetate and homopropargylic acetate. The enantioselectivity of lipase LIP (Pseudomonas sp.) was different from that of lipases PS and AK (Pseudomonas sp.).
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