Stereochemistry of 10-sulfoxidation catalyzed by a soluble delta9 desaturase

Journal Article · Sun Mar 21 00:00:00 EDT 2010 · Organic & Biomolecular Chemistry

DOI:https://doi.org/10.1039/b921753c· OSTI ID:983859

Tremblay, A E; Shanklin, J; Tan, N; Whittle, E; Hodgson, D J; Dawson, B; Buist, P H

The stereochemistry of castor stearoyl-ACP 9 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.

• Research Organization: Brookhaven National Lab. (BNL), Upton, NY (United States)
• Sponsoring Organization: Doe - Office Of Science
• DOE Contract Number: DE-AC02-98CH10886
• OSTI ID: 983859
• Report Number(s): BNL-91158-2010-JA; R&D Project: BO-059; KC0304000; TRN: US201014%%1851
• Journal Information: Organic & Biomolecular Chemistry, Vol. 8, Issue 6; ISSN 1477-0520
• Country of Publication: United States
• Language: English

Related Subjects

08 HYDROGEN
59 BASIC BIOLOGICAL SCIENCES
99 GENERAL AND MISCELLANEOUS//MATHEMATICS, COMPUTING, AND INFORMATION SCIENCE
BEAMS
CASTOR
DATA
HYDROGEN
NUCLEAR MAGNETIC RESONANCE
REMOVAL
STEREOCHEMISTRY
USES