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

2-(2-Acetoxyethyl)cyclohexanone ( 4) was converted into the lactone (−)-( 5) regio- and enantioselectively using 2-oxo-Δ 3-4,5,5-trimethylcyclopentenyl acetyl-CoA monooxygenase, an NADPH-dependent Baeyer-Villiger monooxygenase from camphor grown Pseudomonas putida NCIMB 10007. The lactone (−)-( 5) w...

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Published in:	Bioorganic & medicinal chemistry Vol. 5; no. 2; pp. 253 - 261
Main Authors:	Adger, Brian, Bes, M.Teresa, Grogan, Gideon, McCague, Raymond, Pedragosa-Moreau, Sandrine, Roberts, Stanley M., Villa, Raffaella, Wan, Peter W.H., Willets, Andrew J.
Format:	Journal Article
Language:	English
Published:	England Elsevier Ltd 01-02-1997
Subjects:	Biotransformation Catalysis Magnetic Resonance Spectroscopy NADH, NADPH Oxidoreductases - metabolism Pseudomonas putida - metabolism Stereoisomerism Thioctic Acid - biosynthesis
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Abstract	2-(2-Acetoxyethyl)cyclohexanone ( 4) was converted into the lactone (−)-( 5) regio- and enantioselectively using 2-oxo-Δ 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. A monooxygenase enzyme is employed in the kinetic resolution of the ketone (±)-( 4) to provide optically active lactone (−)-( 5), an intermediate to naturally occurring lipoic acid.
AbstractList	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. 2-(2-Acetoxyethyl)cyclohexanone ( 4) was converted into the lactone (−)-( 5) regio- and enantioselectively using 2-oxo-Δ 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. A monooxygenase enzyme is employed in the kinetic resolution of the ketone (±)-( 4) to provide optically active lactone (−)-( 5), an intermediate to naturally occurring lipoic acid.
Author	Wan, Peter W.H. Willets, Andrew J. McCague, Raymond Pedragosa-Moreau, Sandrine Adger, Brian Bes, M.Teresa Grogan, Gideon Villa, Raffaella Roberts, Stanley M.
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Snippet	2-(2-Acetoxyethyl)cyclohexanone ( 4) was converted into the lactone (−)-( 5) regio- and enantioselectively using 2-oxo-Δ 3-4,5,5-trimethylcyclopentenyl... 2-(2-Acetoxyethyl)cyclohexanone (4) was converted into the lactone (-)-(5) regio- and enantioselectively using 2-oxo-delta 3-4,5,5-trimethylcyclopentenyl...
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SubjectTerms	Biotransformation Catalysis Magnetic Resonance Spectroscopy NADH, NADPH Oxidoreductases - metabolism Pseudomonas putida - metabolism Stereoisomerism Thioctic Acid - biosynthesis
Title	The synthesis of ( R)-(+)-lipoic acid using a monooxygenase-catalysed biotransformation as the key step
URI	https://dx.doi.org/10.1016/S0968-0896(96)00234-9 https://www.ncbi.nlm.nih.gov/pubmed/9061190 https://search.proquest.com/docview/78864853
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