1989 Fiscal Year Final Research Report Summary
Asymmetric Synthesis of Pheromones by the Use of Immobilized Biocatalysts in Organic Solvent Systems
| Project/Area Number |
63560135
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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 |
製造化学・食品
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| Research Institution | Okayama University of Science |
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Principal Investigator |
NAOSHIMA Yoshinobu Okayama University of Science, Faculty of Science, Department of Biological Chemistry, Associate Professor, 理学部, 助教授 (20113194)
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| Project Period (FY) |
1988 – 1989
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| Keywords | Biocatalysts / Immobilized Biocatalysts / Baker's Yeast / Lipases / Plant Cell Cultures / Biotransformation / Pheromones / Asymmetric Synthesis |
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| Research Abstract |
1. Immobilized baker's yeast entrapped in calcium alginate beads of 1-1.5 mm diameter was reusable more than 10 times and stereoselectively reduced ethyl 3- oxobutanoate to the corresponding (S)-hydroxy ester in high chemical and optical yields. The biocatalyst was also active in organic solvent systems including hexane and similarly reduced the keto ester in a high optical yield of 95% ee.
2. Immobilized cells of Nicotiana tabacum entrapped in calcium alginate beads were reusable several times and transformed four different 3-oxobutanoates to the corresponding hydroxy esters in reasonable chemical yields and relatively high optical yields. The consecutive reuse of the immobilized cells enhanced the rates of the biotransformations. The time-course experiments of the biotransformations revealed that the rates of the transformations of 3-oxobutanoates, which have longer n-alkyl chains in their alkoxycarbonyl groups, were higher than those of homologs possessing shorter alkyl chains.
3. Asymmetric synthesis of some pheromones was done employing biotransformation with immobilized biocatalysts such as baker's yeast and lipases entrapped in calcium alginate or glass beads. Both the enantiomers of phoracantholide I (defensive secretion of Phoracantha synonyms), (5Z,13S)-5-tetradecen-13-olide (aggregation pheromone of Cryptolestes grain beetle), (2R,8R)-8-methyl-2-decanol propionate (sex pheromone of some Diabrotica species), and two stereoisomers of 6,10,14-trimethyl-2-pentadecanol (sex pheromone of Corcyra cephalonica Stainton) were therefore synthesized in high optical yields, respectively.
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