The stereochemistry of fatty acid hydroxylation by cytochrome P450BM3

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

doi:10.1016/j.tetlet.2006.10.136

The stereochemistry of fatty acid hydroxylation by cytochrome P450BM3

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

Medicinal Chemistry

Research output: Contribution to journal › Article › Research › peer-review

18 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	133-136
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	1
DOIs	https://doi.org/10.1016/j.tetlet.2006.10.136
Publication status	Published - 1 Jan 2007

Keywords

BM3
CYP102A1
Cytochrome P450
Oxidation mechanism
Regiochemistry
Stereochemistry

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10.1016/j.tetlet.2006.10.136

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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.",

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AU - Matovic, Nick J.

AU - De Voss, James J.

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AB - 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.

KW - BM3

KW - CYP102A1

KW - Cytochrome P450

KW - Oxidation mechanism

KW - Regiochemistry

KW - Stereochemistry

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JO - Tetrahedron Letters

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ER -

The stereochemistry of fatty acid hydroxylation by cytochrome P450BM3

Abstract

Keywords

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