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Issue 6, 2010
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Stereochemistry of 10-sulfoxidation catalyzed by a soluble Δ9 desaturase

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Abstract

The stereochemistry of castor stearoyl-ACP Δ9 desaturase-mediated 10-sulfoxidation has been determined. This was accomplished by 19F NMR analysis of a fluorine-tagged product, 18-fluoro-10-thiastearoyl ACP S-oxide, in combination with a chiral solvating agent, (R)-AMA. Sulfoxidation proceeds with the same stereoselectivity as hydrogen removal from the parent stearoyl substrate. These data validate the use of thia probes to determine the stereochemistry and cryptoregiochemistry of desaturase-mediated oxidations.

Graphical abstract: Stereochemistry of 10-sulfoxidation catalyzed by a soluble Δ9 desaturase

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Publication details

The article was received on 19 Oct 2009, accepted on 05 Dec 2009 and first published on 07 Jan 2010


Article type: Paper
DOI: 10.1039/B921753C
Citation: Org. Biomol. Chem., 2010,8, 1322-1328
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    Stereochemistry of 10-sulfoxidation catalyzed by a soluble Δ9 desaturase

    A. E. Tremblay, N. Tan, E. Whittle, D. J. Hodgson, B. Dawson, P. H. Buist and J. Shanklin, Org. Biomol. Chem., 2010, 8, 1322
    DOI: 10.1039/B921753C

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