The stereochemistry of fatty acid hydroxylation by cytochrome P450(BM3)

The stereochemical preference for the cytochrome P450(BM3)-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 P450(BM3) 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 P450(BM3). (c) 2006 Elsevier Ltd. All rights reserved.