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Towards practical biocatalytic Baeyer-Villiger reactions: applying a thermostable enzyme in the gram-scale synthesis of optically-active lactones in a two-liquid-phase system

Frank Schulz, François Leca, Frank Hollmann and Manfred T. Reetz

Beilstein J. Org. Chem. 2005, 1, No. 10. https://doi.org/10.1186/1860-5397-1-10

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Towards practical biocatalytic Baeyer-Villiger reactions: applying a thermostable enzyme in the gram-scale synthesis of optically-active lactones in a two-liquid-phase system

Frank Schulz, François Leca, Frank Hollmann and Manfred T. Reetz

Beilstein J. Org. Chem. 2005, 1, No. 10. https://doi.org/10.1186/1860-5397-1-10

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Schulz, F.; Leca, F.; Hollmann, F.; Reetz, M. T. Beilstein J. Org. Chem. 2005, 1, No. 10. doi:10.1186/1860-5397-1-10

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TY  - JOUR
A1  - Schulz, Frank
A1  - Leca, François
A1  - Hollmann, Frank
A1  - Reetz, Manfred T.
T1  - Towards practical biocatalytic Baeyer-Villiger reactions: applying a thermostable enzyme in the gram-scale synthesis of optically-active lactones in a two-liquid-phase system
JF  - Beilstein Journal of Organic Chemistry
PY  - 2005///
VL  - 1
SP  - 10
SN  - 1860-5397
DO  - 10.1186/1860-5397-1-10
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.1186/1860-5397-1-10
KW  - Baeyer-Villiger oxidation
KW  - monooxygenases
KW  - two-liquid-phase system
KW  - stereoselective catalysis
KW  - biocatalysis
N2  - Baeyer-Villiger monooxygenases (BVMOs) are extremely promising catalysts useful for enantioselective oxidation reactions of ketones, but organic chemists have not used them widely due to several reasons. These include instability of the enzymes in the case of in vitro and even in vivo systems, reactant/product inhibition, problems with upscaling and the necessity of using specialized equipment. The present study shows that the thermally stable phenylacetone monooxygenase (PAMO) and recently engineered mutants can be used as a practical catalysts for enantioselective Baeyer-Villiger oxidations of several ketones on a preparative scale under in vitro conditions. For this purpose several parameters such as buffer composition, the nature of the solvent system and the co-factor regeneration system were optimized. Overall a fairly versatile and efficient catalytic system for enantioselective laboratory scale BV-oxidations of ketones was developed, which can easily be applied even by those organic chemists who are not well versed in the use of enzymes.
ER  -

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aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
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“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
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benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)