An enzyme cascade synthesis of ε-caprolactone and its oligomers

Sandy Schmidt, Christian Scherkus, Jan Muschiol, Ulf Menyes, Till Winkler, Werner Hummel, Harald Gröger, Andreas Liese, Hans Georg Herz, Uwe T. Bornscheuer

Research output: Contribution to journalArticle

Abstract

Poly-ε-caprolactone (PCL) is chemically produced on an industrial scale in spite of the need for hazardous peracetic acid as an oxidation reagent. Although Baeyer-Villiger monooxygenases (BVMO) in principle enable the enzymatic synthesis of ε-caprolactone (ε-CL) directly from cyclohexanone with molecular oxygen, current systems suffer from low productivity and are subject to substrate and product inhibition. The major limitations for such a biocatalytic route to produce this bulk chemical were overcome by combining an alcohol dehydrogenase with a BVMO to enable the efficient oxidation of cyclohexanol to ε-CL. Key to success was a subsequent direct ring-opening oligomerization of in situ formed ε-CL in the aqueous phase by using lipase A from Candida antarctica, thus efficiently solving the product inhibition problem and leading to the formation of oligo-ε-CL at more than 20 g L-1 when starting from 200 mM cyclohexanol. This oligomer is easily chemically polymerized to PCL.

Original languageEnglish
Pages (from-to)2784-2787
Number of pages4
JournalAngewandte Chemie / International Edition
Volume54
Issue number9
DOIs
Publication statusPublished - 23 Feb 2015

Keywords

  • Baeyer-Villiger monooxygenases
  • Cascade reactions
  • Enzyme catalysis
  • Polymer synthesis
  • ε-caprolactone

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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