The stereochemistry of fatty acid hydroxylation by cytochrome P450BM3

Max J. Cryle, Nick J. Matovic, James J. De Voss

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Abstract

The stereochemical preference for the cytochrome P450BM3-catalysed hydroxylation of tetradecanoic and pentadecanoic acids has been determined via comparison with authentic non-racemic standards utilising enantioselective HPLC. The sub-terminal hydroxylation of these fatty acids by P450BM3 is highly selective for the formation of the R-alcohols. This is the same enantioselectivity as is seen for hexadecanoic acid oxidation but contrasts with a previous report of S-hydroxylation of pentadecanoic acid by P450BM3.

Original languageEnglish
Pages (from-to)133-136
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number1
DOIs
Publication statusPublished - 1 Jan 2007

Keywords

  • BM3
  • CYP102A1
  • Cytochrome P450
  • Oxidation mechanism
  • Regiochemistry
  • Stereochemistry

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