Chemo-enzymatic fluorination of unactivated organic compounds

Nat Chem Biol. 2009 Jan;5(1):26-8. doi: 10.1038/nchembio.128. Epub 2008 Nov 16.

Abstract

Fluorination has gained an increasingly important role in drug discovery and development. Here we describe a versatile strategy that combines cytochrome P450-catalyzed oxygenation with deoxofluorination to achieve mono- and polyfluorination of nonreactive sites in a variety of organic scaffolds. This procedure was applied for the rapid identification of fluorinated drug derivatives with enhanced membrane permeability.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Bacillus megaterium / enzymology
  • Bacterial Proteins / metabolism*
  • Cytochrome P-450 Enzyme System / metabolism*
  • Halogenation*
  • Molecular Structure
  • NADPH-Ferrihemoprotein Reductase / metabolism*
  • Organic Chemicals / chemistry
  • Organic Chemicals / metabolism*
  • Oxidation-Reduction
  • Pharmaceutical Preparations / chemistry
  • Pharmaceutical Preparations / metabolism
  • Substrate Specificity

Substances

  • Bacterial Proteins
  • Organic Chemicals
  • Pharmaceutical Preparations
  • Cytochrome P-450 Enzyme System
  • NADPH-Ferrihemoprotein Reductase
  • flavocytochrome P450 BM3 monoxygenases

Associated data

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