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

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.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Adger B,Bes MT,Grogan G,McCague R,Pedragosa-Moreau S,Roberts SM,Villa R,Wan PW,Willetts AJ

doi

10.1016/s0968-0896(96)00234-9

subject

Has Abstract

pub_date

1997-02-01 00:00:00

pages

253-61

issue

2

eissn

0968-0896

issn

1464-3391

pii

S0968089696002349

journal_volume

5

pub_type

杂志文章

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