Biocatalytic Access to Chiral Polyesters by an Artificial Enzyme Cascade Synthesis

Sandy Schmidt, Hanna C. Büchsenschütz, Christian Scherkus, Andreas Liese, Harald Gröger, Uwe T. Bornscheuer

Research output: Contribution to journalArticleResearchpeer-review

Abstract

Chiral polyesters in general can be employed for versatile biomedical purposes, but in vitro enzyme catalyzed biocatalytic routes by a multiple-step cascade to make these functional biodegradable chiral polyesters have been hardly investigated. Recently, we developed an artificial three-step enzymatic cascade synthesis by combining an alcohol dehydrogenase (ADH), a Baeyer-Villiger monooxygenase (BVMO) and a lipase (CAL-A). Here, we extended this cascade for the synthesis of chiral methyl-substituted oligo-ε-caprolactone derivatives to achieve both, the generation of chirality in a monomer and the subsequent polymerization. Several substrates were examined and provided access to functionalized chiral compounds in high yields (up to >99 %) and optical purities (up to >99 % ee). By subsequent enzymatic enantioselective ring opening of the enantiopure monomers, oligomeric lactones were successfully synthesized. Rotate me! By combining three enzymes (LK-ADH, CHMO, CAL-A), which are evolutionary not connected, to an artificial cascade, optically active chiral oligomers can be synthesized from nonchiral or racemic methyl-substituted cyclohexanol derivatives.

Original languageEnglish
Pages (from-to)3951-3955
Number of pages5
JournalChemCatChem
Volume7
Issue number23
DOIs
Publication statusPublished - 1 Dec 2015

Keywords

  • alcohols
  • dehydrogenation
  • enantioselectivity
  • enzyme catalysis
  • polymerization

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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