Lipase chemoselectivity towards alcohol and thiol acyl acceptors in a transacylation reaction
2010 (English)In: Journal of Molecular Catalysis B: Enzymatic, ISSN 1381-1177, Vol. 66, no 1-2, 120-123 p.Article in journal (Refereed) Published
The lipase chemoselectivity towards an alcohol and a thiol was investigated for the two lipases Candida antarctica lipase B (CalB) and Rhizomucor miehei lipase (Rml). Hexanol and hexanethiol were used as acyl acceptors in a transacylation reaction with ethyl octanoate in cyclohexane. CalB showed the highest chemoselectivity ratio (k(cat)/K-M)(OH)/(k(cat)/K-M)(SH), of 88,000 while the ratio for Rml was 1200. That could be compared with the ratio, k(OH)/k(SH), of 120 for the non-catalyzed reaction. Thus, the enzyme contribution to the chemoselectivity between hexanol and hexanethiol was 730 for CalB and 10 for Rml. High K-M values displayed towards hexanethiol (above 1.8 M) were the largest contribution to the selectivity. No saturation was achieved. The K-M values were more than two orders of magnitude higher than those of hexanol.
Place, publisher, year, edition, pages
2010. Vol. 66, no 1-2, 120-123 p.
Chemoselectiviry, Acylation, Lipase, Kinetics, Active site titration
Biochemistry and Molecular Biology
IdentifiersURN: urn:nbn:se:kth:diva-25232DOI: 10.1016/j.molcatb.2010.04.005ISI: 000280928200015ScopusID: 2-s2.0-77957827548OAI: oai:DiVA.org:kth-25232DiVA: diva2:356637
QC 201010132010-10-132010-10-132011-06-08Bibliographically approved