Selective Oxidations of Organoboron Compounds Catalyzed by Baeyer-Villiger Monooxygenases
| Autor: | Gonzalo de Gonzalo, Leandro H. Andrade, Patrícia B. Brondani, Marco W. Fraaije |
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| Přispěvatelé: | Groningen Biomolecular Sciences and Biotechnology, Biotechnology, Synthetic Organic Chemistry |
| Jazyk: | angličtina |
| Rok vydání: | 2011 |
| Předmět: |
Baeyer-Villiger reaction
Stereochemistry oxidation ENANTIOSELECTIVITY Organoboron chemistry 4-HYDROXYACETOPHENONE MONOOXYGENASE Kinetic resolution Catalysis chemistry.chemical_compound PSEUDOMONAS-FLUORESCENS ACB SÍNTESE ORGÂNICA OXYGENASE Chemoselectivity Phenylacetone monooxygenase PHENYLACETONE-MONOOXYGENASE CYCLOHEXANONE MONOOXYGENASE Enantioselective synthesis General Chemistry Monooxygenase SUBSTRATE-SPECIFICITY Organoboron compounds chemistry Baeyer-Villiger monooxygenases Selectivity boron boron compounds BIOCATALYSTS |
| Zdroj: | Advanced Synthesis & Catalysis, 353(11-12), 2169-2173. WILEY-V C H VERLAG GMBH Repositório Institucional da USP (Biblioteca Digital da Produção Intelectual) Universidade de São Paulo (USP) instacron:USP |
| ISSN: | 1615-4150 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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