Synthesis of natural product precursors by Baeyer-Villiger oxidation with cyclohexanone monooxygenase from Acinetobacter

Ulrich Schwarz-Linek; A Krodel; FA Ludwig; A Schulze; S Rissom; U Kragl; VI Tishkov; M Vogel

doi:10.1055/s-2001-13394

Synthesis of natural product precursors by Baeyer-Villiger oxidation with cyclohexanone monooxygenase from Acinetobacter

Ulrich Schwarz-Linek, A Krodel, FA Ludwig, A Schulze, S Rissom, U Kragl, VI Tishkov, M Vogel

Research output: Contribution to journal › Article › peer-review

49 Citations (Scopus)

Abstract

The Baeyer-Villiger oxidation of the 2-substituted ketones 1 and 3 with the coupled system cyclohexanone monooxygenase from Acinetobacter NCIMB 9871 / formate dehydrogenase from Pseudomonas sp. 101 provides the lactones (R)-2 and (R)-4 with high enantiomeric excess which are precursors in the synthesis of lipoic acid. The symmetrically trisubstituted ketone 5 was oxidised to the lactones 6a and 6b in a ratio of approx. 3:1. The absolute configuration of 6a and 6b was determined by hydrolysis of the racemic lactone with PLE yielding the hydroxycarboxylic acid (-)-7 with known absolute configuration.

Original language	English
Pages (from-to)	947-951
Number of pages	5
Journal	Synthesis
Issue number	6
DOIs	https://doi.org/10.1055/s-2001-13394
Publication status	Published - May 2001

Keywords

oxidation
enzymes
kinetic resolution
hydrolysis
natural products
FORMATE DEHYDROGENASE
AGGREGATION PHEROMONE
(R)-(+)-LIPOIC ACID
LARDOGLYPHUS-KONOI
EPSILON-LACTONES
ACARID MITE
OXYGENASE
RESOLUTION
LARDOLURE

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title = "Synthesis of natural product precursors by Baeyer-Villiger oxidation with cyclohexanone monooxygenase from Acinetobacter",

abstract = "The Baeyer-Villiger oxidation of the 2-substituted ketones 1 and 3 with the coupled system cyclohexanone monooxygenase from Acinetobacter NCIMB 9871 / formate dehydrogenase from Pseudomonas sp. 101 provides the lactones (R)-2 and (R)-4 with high enantiomeric excess which are precursors in the synthesis of lipoic acid. The symmetrically trisubstituted ketone 5 was oxidised to the lactones 6a and 6b in a ratio of approx. 3:1. The absolute configuration of 6a and 6b was determined by hydrolysis of the racemic lactone with PLE yielding the hydroxycarboxylic acid (-)-7 with known absolute configuration.",

keywords = "oxidation, enzymes, kinetic resolution, hydrolysis, natural products, FORMATE DEHYDROGENASE, AGGREGATION PHEROMONE, (R)-(+)-LIPOIC ACID, LARDOGLYPHUS-KONOI, EPSILON-LACTONES, ACARID MITE, OXYGENASE, RESOLUTION, LARDOLURE",

author = "Ulrich Schwarz-Linek and A Krodel and FA Ludwig and A Schulze and S Rissom and U Kragl and VI Tishkov and M Vogel",

year = "2001",

month = may,

doi = "10.1055/s-2001-13394",

language = "English",

pages = "947--951",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "6",

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TY - JOUR

T1 - Synthesis of natural product precursors by Baeyer-Villiger oxidation with cyclohexanone monooxygenase from Acinetobacter

AU - Schwarz-Linek, Ulrich

AU - Krodel, A

AU - Ludwig, FA

AU - Schulze, A

AU - Rissom, S

AU - Kragl, U

AU - Tishkov, VI

AU - Vogel, M

PY - 2001/5

Y1 - 2001/5

N2 - The Baeyer-Villiger oxidation of the 2-substituted ketones 1 and 3 with the coupled system cyclohexanone monooxygenase from Acinetobacter NCIMB 9871 / formate dehydrogenase from Pseudomonas sp. 101 provides the lactones (R)-2 and (R)-4 with high enantiomeric excess which are precursors in the synthesis of lipoic acid. The symmetrically trisubstituted ketone 5 was oxidised to the lactones 6a and 6b in a ratio of approx. 3:1. The absolute configuration of 6a and 6b was determined by hydrolysis of the racemic lactone with PLE yielding the hydroxycarboxylic acid (-)-7 with known absolute configuration.

AB - The Baeyer-Villiger oxidation of the 2-substituted ketones 1 and 3 with the coupled system cyclohexanone monooxygenase from Acinetobacter NCIMB 9871 / formate dehydrogenase from Pseudomonas sp. 101 provides the lactones (R)-2 and (R)-4 with high enantiomeric excess which are precursors in the synthesis of lipoic acid. The symmetrically trisubstituted ketone 5 was oxidised to the lactones 6a and 6b in a ratio of approx. 3:1. The absolute configuration of 6a and 6b was determined by hydrolysis of the racemic lactone with PLE yielding the hydroxycarboxylic acid (-)-7 with known absolute configuration.

KW - oxidation

KW - enzymes

KW - kinetic resolution

KW - hydrolysis

KW - natural products

KW - FORMATE DEHYDROGENASE

KW - AGGREGATION PHEROMONE

KW - (R)-(+)-LIPOIC ACID

KW - LARDOGLYPHUS-KONOI

KW - EPSILON-LACTONES

KW - ACARID MITE

KW - OXYGENASE

KW - RESOLUTION

KW - LARDOLURE

UR - http://www.scopus.com/inward/record.url?scp=0343832155&partnerID=8YFLogxK

U2 - 10.1055/s-2001-13394

DO - 10.1055/s-2001-13394

M3 - Article

SN - 0039-7881

SP - 947

EP - 951

JO - Synthesis

JF - Synthesis

IS - 6

ER -

Synthesis of natural product precursors by Baeyer-Villiger oxidation with cyclohexanone monooxygenase from Acinetobacter

Abstract

Keywords

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