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...

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Veröffentlicht in:	Organic & biomolecular chemistry 2010-03, Vol.8 (6), p.1322-1328
Hauptverfasser:	Tremblay, Amy E, Tan, Nigel, Whittle, Ed, Hodgson, Derek J, Dawson, Brian, Buist, Peter H, Shanklin, John
Format:	Artikel
Sprache:	eng
Schlagworte:	08 HYDROGEN BASIC BIOLOGICAL SCIENCES BEAMS Biocatalysis CASTOR DATA GENERAL AND MISCELLANEOUS//MATHEMATICS, COMPUTING, AND INFORMATION SCIENCE HYDROGEN Magnetic Resonance Spectroscopy NUCLEAR MAGNETIC RESONANCE REMOVAL Solubility Solvents - chemistry Stearates - chemistry Stearates - metabolism Stearoyl-CoA Desaturase - chemistry Stearoyl-CoA Desaturase - metabolism STEREOCHEMISTRY Stereoisomerism Substrate Specificity Sulfoxides - chemistry USES
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Zusammenfassung:	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.
ISSN:	1477-0520 1477-0539
DOI:	10.1039/b921753c