title: Stereochemistry of 10-sulfoxidation catalyzed by a soluble Delta9 desaturase.
abstract: 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.
authors.affiliation: Department of Chemistry, Carleton University, 1125 Colonel By Drive, Ottawa, Ontario, Canada K1S 5B6.
authors.forename: Amy E
authors.initials: AE
authors.lastname: Tremblay
authors.forename: Nigel
authors.initials: N
authors.lastname: Tan
authors.forename: Ed
authors.initials: E
authors.lastname: Whittle
authors.forename: Derek J
authors.initials: DJ
authors.lastname: Hodgson
authors.forename: Brian
authors.initials: B
authors.lastname: Dawson
authors.forename: Peter H
authors.initials: PH
authors.lastname: Buist
authors.forename: John
authors.initials: J
authors.lastname: Shanklin
mesh_terms: 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*
chemical_list: D012997:Solvents; D013228:Stearates; D013454:Sulfoxides; D013230:Stearoyl-CoA Desaturase