Selective Oxidations of Organoboron Compounds Catalyzed by Baeyer-Villiger Monooxygenases

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

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

26 Citations (Scopus)
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Abstract

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.

Original languageEnglish
Pages (from-to)2169-2173
Number of pages5
JournalAdvanced Synthesis & Catalysis
Volume353
Issue number11-12
DOIs
Publication statusPublished - Aug-2011

Keywords

  • Baeyer-Villiger reaction
  • Baeyer-Villiger monooxygenases
  • boron
  • boron compounds
  • oxidation
  • PSEUDOMONAS-FLUORESCENS ACB
  • PHENYLACETONE-MONOOXYGENASE
  • 4-HYDROXYACETOPHENONE MONOOXYGENASE
  • CYCLOHEXANONE MONOOXYGENASE
  • SUBSTRATE-SPECIFICITY
  • ENANTIOSELECTIVITY
  • BIOCATALYSTS
  • OXYGENASE

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