Stereochemistry of 10-sulfoxidation catalyzed by a soluble Δ9 desaturase

Amy E. Tremblay; Nigel Tan; Ed Whittle; Derek J. Hodgson; Brian Dawson; Peter H. Buist; John Shanklin

doi:10.1039/B921753C

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Stereochemistry of 10-sulfoxidation catalyzed by a soluble Δ⁹ desaturase†

Amy E. Tremblay,^a Nigel Tan,^a Ed Whittle,^b Derek J. Hodgson,^c Brian Dawson,^c Peter H. Buist*^a and John Shanklin*^b

Author affiliations

* Corresponding authors

^a Department of Chemistry, Carleton University, 1125 Colonel By Drive, Ottawa, Ontario, Canada

^b Brookhaven National Laboratory, Department of Biology, Upton, NY, USA

^c Centre for Biologics Research, Biologics and Genetic Therapies Directorate, Health Canada, Tunney's Pasture, Ottawa, Ontario, Canada

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.

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Supplementary files

Experimental details and characterization data PDF (3468K)

Article information

DOI: https://doi.org/10.1039/B921753C
Article type: Paper
Submitted: 19 Oct 2009
Accepted: 05 Dec 2009
First published: 07 Jan 2010

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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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Organic & Biomolecular Chemistry