Enzymatic separation of cis/trans 1,4-cyclohexanedimethanol mixtures by mono- and polytransesterification

Shimona Geresh, Elizabeth Elbaz, Robert Glaser

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

Lipase-catalyzed poly- and monotransesterification reactions were used in kinetic separations of a commercial mixture of cis,trans-1,4-cyclohexanedimethanol. The reactions were performed with lipases from various sources and with mono- and diesters as the acylating reagents. In a series of monotransesterifications, the highest diastereoselectivity (1:6.5) was obtained with β-chloroethyl hydrocinnamate as the acyl donor and lipase from Pseudomonas fluorescens. Polycondensations with fumarate esters using lipase from porcine pancreas afforded moderate diastereoselectivity (about 1:4.5) for the cis/trans monocondensate, and markedly increased diastereoselectivity (about 1:24) for the cis/trans dicondensate product.

Original languageEnglish
Pages (from-to)4939-4944
Number of pages6
JournalTetrahedron
Volume49
Issue number22
DOIs
StatePublished - 28 May 1993

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Enzymatic separation of cis/trans 1,4-cyclohexanedimethanol mixtures by mono- and polytransesterification'. Together they form a unique fingerprint.

Cite this