Lipase-catalyzed hydrolysis: effect of alcohol configuration on the stereobias for 2-methyloctanoic acid

The reactivities of 2-methyloctanoic acid esters of rac-2,3-isopropylidene glycerol and rac-glycidol have been examined with several commercial lipase preparations. The S configuration of the acid always reacted faster. The (S)-2,3-isopropylidene glycerol esters and (R)-glycidol esters reacted faste...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 1993-02, Vol.41 (2), p.319-321
Main Author: Sonnet, Philip E
Format: Article
Language:English
Subjects:
Biological and medical sciences
Candida rugosa
Food industries
Fundamental and applied biological sciences. Psychology
General aspects
Methods of analysis, processing and quality control, regulation, standards
Mucor miehei
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Summary:The reactivities of 2-methyloctanoic acid esters of rac-2,3-isopropylidene glycerol and rac-glycidol have been examined with several commercial lipase preparations. The S configuration of the acid always reacted faster. The (S)-2,3-isopropylidene glycerol esters and (R)-glycidol esters reacted faster than did the esters of the enantiomeric alcohols. The effect of alcohol configuration on the stereobias of the lipase-catalyzed hydrolysis, however, was modest, which is consistent with a mechanism whereby the oxygenated alcohols enable binding of catalyst to substrate while offering only slight changes to the energetics of the catalytic step. The most promising candidate alcohols for resolving 2-methyloctanoic acid by hydrolysis appear to be rac-2,3-isopropylidene glycerol (Candida rugosa lipase) and (S)-glycidol (Mucor miehei lipase).
ISSN:0021-8561
1520-5118
DOI:10.1021/jf00026a036