Stereochemistry of 10-sulfoxidation catalyzed by a soluble Δ 9 desaturase

AE Tremblay, N Tan, E Whittle, DJ Hodgson…

Index: Tremblay, Amy E.; Tan, Nigel; Whittle, Ed; Hodgson, Derek J.; Dawson, Brian; Buist, Peter H.; Shanklin, John Organic and Biomolecular Chemistry, 2010 , vol. 8, # 6 p. 1322 - 1328

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Citation Number: 5

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 ...