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

Research output: Contribution to journalArticleResearchpeer-review

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

Fingerprint

Regioselectivity
Stereoisomerism
Enantioselectivity
Lactones
Mixed Function Oxygenases
Oxidation-Reduction
Oxidoreductases
Experiments
carvone

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Novel concurrent redox cascades of (R)- and (S)-carvones enables access to carvo-lactones with distinct regio- and enantioselectivity. / Iqbal, Naseem; Stewart, Jon D.; Macheroux, Peter; Rudroff, Florian; Mihovilovic, Marko D.

In: Tetrahedron, Vol. 74, No. 52, 27.12.2018, p. 7389-7394.

Research output: Contribution to journalArticleResearchpeer-review

Iqbal, Naseem ; Stewart, Jon D. ; Macheroux, Peter ; Rudroff, Florian ; Mihovilovic, Marko D. / Novel concurrent redox cascades of (R)- and (S)-carvones enables access to carvo-lactones with distinct regio- and enantioselectivity. In: Tetrahedron. 2018 ; Vol. 74, No. 52. pp. 7389-7394.
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