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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 7
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Original Articles

Systematic Investigation of the Kinetic Resolution of 3-Hydroxy Fatty Acid Esters Using Candida antarctica Lipase B (CALB) and the Influence of Competing Oligomerization on the Enantiomeric Ratios

Markus Braner Hochschule Darmstadt, Fachbereich Chemie und Biotechnologie, Darmstadt, Germany
,
Stefan Zielonka Hochschule Darmstadt, Fachbereich Chemie und Biotechnologie, Darmstadt, Germany
,
Sylvia Auras Hochschule Darmstadt, Fachbereich Chemie und Biotechnologie, Darmstadt, Germany
&
Stefan H. Hüttenhain Hochschule Darmstadt, Fachbereich Chemie und Biotechnologie, Darmstadt, GermanyCorrespondence[email protected]
Pages 1019-1025 | Received 21 Oct 2010, Published online: 16 Dec 2011
 
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Abstract

The kinetic resolution of 3-hydroxy fatty acid esters C8:0 to C16:0 with Candida antarctica lipase B shows common plots of the enantiomeric excesses of the product and substrate, respectively, versus the conversion and an enantiomeric ratio E of 27 calculated from ee(p). Differences in E, either calculated from the products or the substrates, could be explained by competing oligomerization as a second substrate-consuming process. This reaction is slow compared to acylation, and the remaining enantiomer was oligomerized.

GRAPHICAL ABSTRACT

ACKNOWLEDGMENT

We gratefully acknowledge the financial support of ZFE, Hochschule Darmstadt.

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