Baeyer‐Villiger Oxidations

Flitsch, Sabine L.; Grogan, Gideon

doi:10.1002/9783527618262.ch16e

Cited by 23 publications

(2 citation statements)

References 127 publications

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“…BVMOs, in particular CHMO, are versatile biocatalysts that have been widely used in synthetic biotransformations. − They contain a flavin moiety as the prosthetic group and utilize NAD(P)H as a stoichiometric cofactor (see Figure ). In view of the requirement for cofactor regeneration, these reactions are generally performed with whole microbial cells in a fermentation mode.…”

Section: 22 Bvmosmentioning

confidence: 99%

The Baeyer−Villiger Reaction: New Developments toward Greener Procedures

2004

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Section: 22 Bvmosmentioning

confidence: 99%

The Baeyer−Villiger Reaction: New Developments toward Greener Procedures

2004

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“…The microbial Baeyer−Villiger oxidation (Scheme ) has received substantial attention in recent years as a valuable tool for the transformation of prochiral or racemic ketones into optically pure lactones which are attractive intermediates in organic synthesis. Thanks to progress in genome deciphering during the past years, an increasing diversity of Baeyer−Villiger monooxygenases (BVMOs) has become available as versatile catalysts for such stereoselective transformations which fulfill the requirements of sustainable and green chemistry strategies . Until recently, widespread application of such catalytic entities was limited by a general obstacle of biocatalysis: While access to both antipodal forms of a product can be achieved with de novo designed synthetic catalysts, no generally applicable strategy is available to provide enantiocomplementarity in biocatalysis.…”

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Microbial Baeyer−Villiger Oxidation: Stereopreference and Substrate Acceptance of Cyclohexanone Monooxygenase Mutants Prepared by Directed Evolution

et al. 2006

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[reaction: see text] An array of random mutants of cyclohexanone monooxygenase (CHMO) from Acinetobacter sp. NCIMB 9871 was screened against a library of structurally diverse ketones for modifications in the substrate acceptance profile and stereopreference of the enzymatic Baeyer-Villiger biooxidation. While the set of mutant biocatalysts was initially evolved for the enantiocomplementary oxidation of 4-hydroxycyclohexanone, improved and/or divergent stereoselectivities were observed for several substrates. In addition, expanded substrate acceptance to facilitate biotransformation of sterically demanding ketones was found.

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Enzymes, Directed Evolution

Reetz

2009

Encyclopedia of Industrial Biotechnology

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Directed evolution has emerged as a powerful method for engineering the catalytic profile of enzymes. It is based on repetitive cycles of random gene mutagenesis and expression coupled with efficient high‐throughput screening or selection for a given catalytic property such as thermostability, substrate acceptance, and/or enantioselectivity. In the 1990s, directed evolution was established on a broad front by applying standard mutagenesis methods such as error‐prone polymerase chain reaction (epPCR), saturation mutagenesis, and DNA shuffling. The current challenge is to devise optimal strategies for probing protein sequence space, thereby allowing for fast directed evolution. This article covers the progress of the last few years.

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Baeyer‐Villiger Oxidations

Cited by 23 publications

References 127 publications

The Baeyer−Villiger Reaction: New Developments toward Greener Procedures

The Baeyer−Villiger Reaction: New Developments toward Greener Procedures

Microbial Baeyer−Villiger Oxidation: Stereopreference and Substrate Acceptance of Cyclohexanone Monooxygenase Mutants Prepared by Directed Evolution

Enzymes, Directed Evolution

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