The synthesis of (R)-(+)-lipoic acid using a monooxygenase-catalysed biotransformation as the key step

Bioorg Med Chem. 1997 Feb;5(2):253-61. doi: 10.1016/s0968-0896(96)00234-9.

Abstract

2-(2-Acetoxyethyl)cyclohexanone (4) was converted into the lactone (-)-(5) regio- and enantioselectively using 2-oxo-delta 3-4,5,5-trimethylcyclopentenyl acetyl-CoA monooxygenase, an NADPH-dependent Baeyer-Villiger monooxygenase from camphor grown Pseudomonas putida NCIMB 10007. The lactone (-)-(5) was converted into (R)-(+)-lipoic acid in six steps. In contrast cyclopentanone monooxygenase, an NADPH-dependent Baeyer-Villiger monooxygenase from cyclopentanol-grown Pseudomonas sp. NCIMB 9872 selectively oxidized the (S)-enantiomer of the ketone (4) giving better access to optically enriched, naturally occurring lipoic acid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biotransformation
  • Catalysis
  • Magnetic Resonance Spectroscopy
  • NADH, NADPH Oxidoreductases / metabolism*
  • Pseudomonas putida / metabolism
  • Stereoisomerism
  • Thioctic Acid / biosynthesis*

Substances

  • Thioctic Acid
  • 2-oxo-delta(3)-4,5,5--trimethylcyclopentenyl acetyl-CoA monooxygenase
  • NADH, NADPH Oxidoreductases