| Kinetically controlled synthesis of monoglyceryl esters from chiral and prochiral acids methyl esters catalyzed by immobilized Rhizomucor miehei lipase. | |
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MedLine Citation:
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PMID: 20855204 Owner: NLM Status: In-Process |
Abstract/OtherAbstract:
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Partial acylation of only one primary hydroxyl group of glycerol generates a chiral center at position 2. Rhizomucor miehei lipase (RML) catalyzes the kinetically controlled transesterification of different aromatic carboxylic acids methyl esters with glycerol. High synthetic yields of glyceryl esters (around 70-80%) were obtained even in the presence of significant concentrations of water (from 5% to 20%). After a long incubation of the reaction mixture in the presence of the biocatalyst only pure free acid was obtained. Other lipases (from Geobacillus thermocatenulatus and from Thermomyces lanuginose) also catalyzed similar kinetically controlled transesterifications although less efficiently. RML immobilized on Sepharose-Q showed a high activity and specificity, compared to the immobilization by other techniques, only producing monoglyceryl esters with all substrates. In particular, monoglyceryl-phenylmalonate product was synthesized in 82% overall yield and >99% diastereomeric excess at pH 7.0 and 37°C and 90% glycerol. |
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Authors:
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Andreina Acosta; Marco Filice; Gloria Fernandez-Lorente; Jose M Palomo; Jose M Guisan |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2010-08-31 |
Journal Detail:
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Title: Bioresource technology Volume: 102 ISSN: 1873-2976 ISO Abbreviation: Bioresour. Technol. Publication Date: 2011 Jan |
Date Detail:
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Created Date: 2011-01-03 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 9889523 Medline TA: Bioresour Technol Country: England |
Other Details:
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Languages: eng Pagination: 507-12 Citation Subset: IM |
Copyright Information:
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Copyright © 2010 Elsevier Ltd. All rights reserved. |
Affiliation:
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Departamento de Biocatálisis, Instituto de Catálisis (CSIC), Spain. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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