593-12-4Relevant articles and documents
Stereochemistry of 10-sulfoxidation catalyzed by a soluble Δ9 desaturase
Tremblay, Amy E.,Tan, Nigel,Whittle, Ed,Hodgson, Derek J.,Dawson, Brian,Buist, Peter H.,Shanklin, John
experimental part, p. 1322 - 1328 (2010/06/16)
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.
Synthesis of ω-Tritiated and ω-Fluorinated Analogues of the Trail Pheromone of Subterranean Termites
Carvalho, Joan F.,Prestwich, Glenn D.
, p. 1251 - 1258 (2007/10/02)
A series of unsaturated ω-fluoro alcohols have been prepared stereoselectively.These simple compounds are structural analogues of the trail pheromone of termites in the genus Reticulitermes.The toxicity of these ω-fluoro alcohols to R. flavipes is maximal for the C12 alcohols, and the attractiveness of these C12 analogues increases in the order saturated alkanol -12-fluoro alcohols and a -nonfluorinated analogue were prepared to examine the catabolism of the pheromone analogues.