Stereochemistry of 10-sulfoxidation catalyzed by a soluble Delta9 desaturase.
The stereochemistry of castor stearoyl-ACP Delta(9) desaturase-mediated 10-sulfoxidation has been determined. This was accomplished by (19)F 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.
Tremblay
Amy E
AE
Department of Chemistry, Carleton University, 1125 Colonel By Drive, Ottawa, Ontario, Canada K1S 5B6.
Tan
Nigel
N
Whittle
Ed
E
Hodgson
Derek J
DJ
Dawson
Brian
B
Buist
Peter H
PH
Shanklin
John
J
D055162:Biocatalysis; D009682:Magnetic Resonance Spectroscopy; D012995:Solubility; D012997:Solvents / Q000737:chemistry; D013228:Stearates / Q000737:chemistry* / Q000378:metabolism*; D013230:Stearoyl-CoA Desaturase / Q000737:chemistry* / Q000378:metabolism*; D013237:Stereoisomerism; D013379:Substrate Specificity; D013454:Sulfoxides / Q000737:chemistry*
D012997:Solvents; D013228:Stearates; D013454:Sulfoxides; D013230:Stearoyl-CoA Desaturase