Stereochemistry of 10-sulfoxidation catalyzed by a soluble Δ9 desaturase?

Organic & Biomolecular Chemistry Pub Date: 2010-01-07 DOI: 10.1039/B921753C

Abstract

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.

Graphical abstract: Stereochemistry of 10-sulfoxidation catalyzed by a soluble Δ9 desaturase
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