Novel concurrent redox cascades of (R)- and (S)-carvones enables access to carvo-lactones with distinct regio- and enantioselectivity

Naseem Iqbal, Jon D. Stewart, Peter Macheroux, Florian Rudroff*, Marko D. Mihovilovic

*Corresponding author for this work

Research output: Contribution to journalArticle

Abstract

Within this study, we investigated a one-pot enzymatic redox cascade composed of different enoate reductases (5 EREDs from diverse bacterial origins) and various Baeyer-Villiger monooxygenases (4 BVMOs) with complementary regioselectivity that enabled access to six out of eight carvo-lactone stereoisomers starting from readily available natural carvones. Applicability of this two-step cascade was demonstrated by preparative scale experiments yielding up to 76% of the desired chiral carvolactone.

Original languageEnglish
Pages (from-to)7389-7394
Number of pages6
JournalTetrahedron
Volume74
Issue number52
DOIs
Publication statusPublished - 27 Dec 2018

Keywords

  • Baeyer-Villiger monooxygenases
  • Biotransformation
  • Carvone
  • Cascade reaction
  • Eonate reductase
  • Redox enzymes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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