56909-05-8Relevant articles and documents
Stereochemistry of 10-sulfoxidation catalyzed by a soluble Δ9 desaturase
Tremblay, Amy E.,Tan, Nigel,Whittle, Ed,Hodgson, Derek J.,Dawson, Brian,Buist, Peter H.,Shanklin, John
, p. 1322 - 1328 (2010)
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.