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Selective Oxidations of Organoboron Compounds Catalyzed by Baeyer-Villiger Monooxygenases

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논문

Selective Oxidations of Organoboron Compounds Catalyzed by Baeyer-Villiger Monooxygenases

학술지

Advanced synthesis & catalysis

저자명

Brondani, Patrí cia B.; de  Gonzalo, Gonzalo; Fraaije, Marco W.; Andrade, Leandro H.

초록

<P><B>Abstract</B></P><P>The applicability of Baeyer&ndash;Villiger monooxygenases (BVMOs) in organoboron chemistry has been explored through testing chemo&#8208; and enantioselective oxidations of a variety of boron&#8208;containing aromatic and vinylic compounds. Several BVMOs, namely: phenylacetone monooxygenase (PAMO), M446G PAMO mutant, 4&#8208;hydroxyacetophenone monooxygenase (HAPMO) and cyclohexanone monooxygenase (CHMO) were used in this study. The degree of chemoselectivity depends on the type of BVMO employed, in which the biocatalysts prefer boron&#8208;carbon oxidation over Baeyer&ndash;Villiger oxidation or epoxidation. Interestingly, it was discovered that PAMO can be used to perform kinetic resolution of boron&#8208;containing compounds with good enantioselectivities. These findings extend the known biocatalytic repertoire of BVMOs by showing a new family of compounds that can be oxidized by these enzymes.</P>

발행연도

2011

ISSN

1615-4150

ISSN

1615-4169

353

11

페이지

pp.2169-2173

주제어

Baeyer&ndash; Villiger reaction; Baeyer&ndash; Villiger monooxygenases; boron; boron compounds; oxidation;

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논문; 2011-08-01

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