Ring-opening of ω-substituted lactones by Novozym 435 : selectivity issues and application to iterative tandem catalysis

A.R.A. Palmans, B.A.C. As, van, J. Buijtenen, van, E.W. Meijer

Research output: Chapter in Book/Report/Conference proceedingChapterAcademic

4 Citations (Scopus)

Abstract

The enantioselectivity of the Novozym® 435 catalysed ring-opening of lactones is related to the conformation of the ester: cisoid lactones show S-selectivity or no selectivity while transoid lactones show a pronounced R-selectivity. The inability of Novozym 435 to polymerise 6-MeCL stems from its opposing selectivities for the alcohol and acyl moiety. By combining Novozym 435 with a racemisation catalyst, unreactive terminal alcohols in the S-configuration can be turned into reactive terminal alcohols of the R-configuration which can propagate. Combining 2 different catalysts that work together to accomplish propagation, also referred to as iterative tandem catalysis, is an elegant approach to convert a racemic monomer quantitatively into a homochiral polymer.
Original languageEnglish
Title of host publicationPolymer biocatalysis and biomaterials II
EditorsH.N. Cheng, R.A. Gross
Place of PublicationWashington
PublisherAmerican Chemical Society
Pages230-244
ISBN (Print)978-0-8412-6970-5
DOIs
Publication statusPublished - 2008

Publication series

NameACS symposium series
Volume999
ISSN (Print)0097-6156

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