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Reaction conditions for the resolution of 2-methylalkanoic acids in esterification and hydrolysis with lipase from Candida cylindracea
Mid Sweden University.ORCID iD: 0000-0002-9577-832X
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1991 (English)In: Applied Microbiology and Biotechnology, ISSN 01757598 (ISSN), Vol. 35, no 5, 572-578 p.Article in journal (Refereed) Published
Abstract [en]

We have demonstrated resolution of 2-methylalkanoic acids using lipase from Candida cylindracea as a catalyst. The resolution of 2-methyldecanoic acid was more successful than that of 2-methylbutyric acid both by esterification and hydrolysis. This indicates that the resolution of the acid is dependent on the chain length of the acid moiety. The chain length of the alcohol moiety of the ester affected the resolution of the long-chain acid only. Using esterification, (R)-2-methyldecanoic acid was produced in an enantiomeric excess (e.e.) of 95% (E = 40). If the enantiomeric ratio is low (E = 3.6), as in the resolution of 2-methylbutyric acid, esterification combined with a high equilibrium conversion could be used to yield the remaining acid in a high e.e. In the hydrolytic reactions, the e.e. and the equilibrium conversion were dependent on the pH and the presence of CaCl2. When octyl 2-methyldecanoate was hydrolysed at pH 8.0 in the presence of CaCl2, the (S)-acid was formed with an e.e. of 80% (E = 9), but when the hydrolysis was carried out at pH 7.5 without CaCl2, a very low e.e. and a low equilibrium conversion were observed. The latter conditions allowed the esterification of 2-methyldecanoic acid with 1-octanol even in aqueous medium.

Place, publisher, year, edition, pages
1991. Vol. 35, no 5, 572-578 p.
Keyword [en]
2 methylalkanoic acid, triacylglycerol lipase, unclassified drug, article, biotechnology, candida, esterification, hydrolysis, nonhuman, Candida cylindracea
National Category
Organic Chemistry
URN: urn:nbn:se:kth:diva-74876OAI: diva2:490136
Language of Original Document: English NR 20140805Available from: 2012-02-03 Created: 2012-02-03 Last updated: 2012-02-03Bibliographically approved

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Berglund, P.
Organic Chemistry

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