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Highly enantioselective resolution of β-amino esters by Candida antarctica lipase A immobilized in mesocellular foam: application to dynamic kinetic resolution
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2010 (English)In: ChemCatChem, ISSN 1867-3899, Vol. 2, no 5, 534-538 p.Article in journal (Refereed) Published
Abstract [en]

Candida antarctica lipase A (CALA) immobilized in functionalized mesocellular foam in the presence of sucrose, followed by lyophilization, led to a dramatic increase in the enantioselectivity as well as an improved thermostability of the enzyme. The immobilized lipase was used for kinetic resolution (KR) and dynamic kinetic resolution (DKR) of the β-amino ester, ethyl 3-amino-3-phenylpropanoate. The temperature of optimum activity of CALA shifted from 20–30 °C to 80–90 °C on immobilization in the MCF. An “enantiomeric ratio” E (E=νA/νB; νA and νB are the rate constants for entantiomers A and B) of 69 and a conversion of 43 % in 1 h were obtained at 80 °C, whereas non-immobilized CALA lost its activity at T≥50 °C. The obtained immobilized CALA showed an E value of greater than 500 at 22 °C. Combination of the immobilized CALA with a ruthenium complex, acting as a racemization catalyst, allowed for a successful DKR of ethyl 3-amino-3-phenylpropanoate resulting in 85 % conversion and 89 % ee.

Place, publisher, year, edition, pages
2010. Vol. 2, no 5, 534-538 p.
Keyword [en]
amino esters, enzyme catalysis, immobilization, kinetic resolution, supported catalysts
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-47405DOI: 10.1002/cctc.201000027OAI: oai:DiVA.org:su-47405DiVA: diva2:373953
Funder
EU, FP7, Seventh Framework ProgrammeKnut and Alice Wallenberg Foundation
Available from: 2010-12-02 Created: 2010-12-02 Last updated: 2011-01-04Bibliographically approved

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Shakeri, MozaffarEngström, KarinSandström, Anders G.Bäckvall, Jan-Erling
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