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From the same journal

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

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Author(s)

  • B Adger
  • M T Bes
  • G Grogan
  • R McCague
  • S P Moreau
  • S M Roberts
  • R Villa
  • P W H Wan
  • A J Willetts

Department/unit(s)

Publication details

JournalBioorganic and Medicinal Chemistry
DatePublished - Feb 1997
Issue number2
Volume5
Number of pages9
Pages (from-to)253-261
Original languageEnglish

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. (C) 1997, Elsevier Science Ltd.

    Research areas

  • ALPHA-LIPOIC ACID, R-(+)-ALPHA-LIPOIC ACID, (R)-(+)-ALPHA-LIPOIC ACID, PSEUDOMONAS-PUTIDA, ENANTIOSPECIFIC SYNTHESIS, ENANTIOSELECTIVE SYNTHESIS, XANTHOBACTER SP, COMPLEXES, 1,2-MONOOXYGENASE, OXYGENASE

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