The stereochemistry of fatty acid hydroxylation by cytochrome P450BM3

Cryle, Max; Matovic, Nicholas J.; De Voss, James J.

doi:10.1016/j.tetlet.2006.10.136

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The stereochemistry of fatty acid hydroxylation by cytochrome P450_BM3

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Cryle, Max
Department of Biomolecular Mechanisms, Max Planck Institute for Medical Research, Max Planck Society;

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http://www.sciencedirect.com/science/article/pii/S0040403906021642/pdfft?md5=c04d3c1c1458b2328ef989019f3a9ff4&pid=1-s2.0-S0040403906021642-main.pdf
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Citation

Cryle, M., Matovic, N. J., & De Voss, J. J. (2007). The stereochemistry of fatty acid hydroxylation by cytochrome P450_BM3. Tetrahedron Letters, 48(1), 133-136. doi:10.1016/j.tetlet.2006.10.136.

Cite as: https://hdl.handle.net/11858/00-001M-0000-002C-A795-A

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.