Synthesis of Fenthion Sulfoxide and Fenoxon Sulfoxide Enantiomers:  Effect of Sulfur Chirality on Acetylcholinesterase Activity

• Published in: Chemical research in toxicology Vol. 20; no. 2; pp. 257 - 262
• Main Authors: Gadepalli, Rama Sarma V. S, Rimoldi, John M, Fronczek, Frank R, Nillos, Mae, Gan, Jay, Deng, Xin, Rodriguez-Fuentes, Gabriela, Schlenk, Daniel
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 01.02.2007
• Subjects: Acetylcholinesterase - chemistry; Acetylcholinesterase - drug effects; Crystallography, X-Ray; Enzyme Activation - drug effects; Fenthion - analogs & derivatives; Fenthion - chemical synthesis; Fenthion - chemistry; Fenthion - pharmacology; Models, Molecular; Molecular Structure; Stereoisomerism; Structure-Activity Relationship; Sulfoxides - chemical synthesis; Sulfoxides - chemistry; Sulfoxides - pharmacology

Earlier reports have demonstrated that recombinant flavin-containing monooxygenase 1 (FMO1) catalyzes the oxidation of the organophosphate pesticide fenthion to (+)-fenthion sulfoxide in a stereoselective fashion. In order to elucidate the absolute configuration of the sulfoxide metabolite produced,...