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, 48 1: 133-136. doi:10.1016/j.tetlet.2006.10.136


Author Cryle, Max J.
Matovic, Nick J.
De Voss, James J.
Title The stereochemistry of fatty acid hydroxylation by cytochrome P450(BM3)
Formatted title
The stereochemistry of fatty acid hydroxylation by cytochrome P450BM3
Journal name Tetrahedron Letters   Check publisher's open access policy
ISSN 0040-4039
Publication date 2007-01
Year available 2006
Sub-type Article (original research)
DOI 10.1016/j.tetlet.2006.10.136
Volume 48
Issue 1
Start page 133
End page 136
Total pages 4
Place of publication Oxford, England
Publisher Pergamon-elsevier Science Ltd
Collection year 2008
Language eng
Subject 250301 Organic Chemical Synthesis
270199 Biochemistry and Cell Biology not elsewhere classified
C1
780103 Chemical sciences
780105 Biological sciences
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). (c) 2006 Elsevier Ltd. All rights reserved.
Keyword Chemistry, Organic
cytochrome p450
BM3
CYP102A1
stereochemistry
regiochemistry
oxidation mechanism
Oxidation
Esters
Cyclopropyl
P450bm-3
Reagents
Q-Index Code C1
Q-Index Status Confirmed Code

 
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Created: Mon, 18 Feb 2008, 16:04:54 EST