The stereochemistry of fatty acid hydroxylation by cytochrome P450(BM3)
Cryle, Max J., Matovic, Nick J. and De Voss, James J. (2007) The stereochemistry of fatty acid hydroxylation by cytochrome P450(BM3). Tetrahedron Letters, 481: 133-136. doi:10.1016/j.tetlet.2006.10.136
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.