Selective Oxidations of Organoboron Compounds Catalyzed by Baeyer-Villiger Monooxygenases

Patricia B. Brondani, Gonzalo de Gonzalo, Marco W. Fraaije, Leandro H. Andrade*

*Bijbehorende auteur voor dit werk

OnderzoeksoutputAcademicpeer review

26 Citaten (Scopus)
525 Downloads (Pure)

Samenvatting

The applicability of Baeyer-Villiger monooxygenases (BVMOs) in organoboron chemistry has been explored through testing chemo-and enantioselective oxidations of a variety of boron-containing aromatic and vinylic compounds. Several BVMOs, namely: phenylacetone monooxygenase (PAMO), M446G PAMO mutant, 4-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-carbon oxidation over Baeyer-Villiger oxidation or epoxidation. Interestingly, it was discovered that PAMO can be used to perform kinetic resolution of boron-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.

Originele taal-2English
Pagina's (van-tot)2169-2173
Aantal pagina's5
TijdschriftAdvanced Synthesis & Catalysis
Volume353
Nummer van het tijdschrift11-12
DOI's
StatusPublished - aug-2011

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