Unexpected Subtilisin-Catalyzed Hydrolysis of a Sulfinamide Bond in Preference to a Carboxamide Bond in N-Acyl Sulfinamides

Subtilisin Carlsberg-catalyzed hydrolysis of N-chloroacetyl p-toluenesulfinamide favored cleavage of the sulfinamide (S(O)−N) bond with a minor amount (∼25%) of the expected carboxamide (C(O)−N) bond. The sulfinamide hydrolysis was enantioselective (E ∼ 17) and yielded remaining starting material en...

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Veröffentlicht in:	Journal of the American Chemical Society 2005-05, Vol.127 (18), p.6536-6537
Hauptverfasser:	Mugford, Paul F, Magloire, Vladimir P, Kazlauskas, Romas J
Format:	Artikel
Sprache:	eng
Schlagworte:	Amides - chemistry Amides - metabolism Biological and medical sciences Catalysis Fundamental and applied biological sciences. Psychology Hydrolysis Mechanisms. Catalysis. Electron transfer. Models Molecular biophysics Pancreatic Elastase - chemistry Pancreatic Elastase - metabolism Physical chemistry in biology Stereoisomerism Substrate Specificity Subtilisin - chemistry Subtilisin - metabolism Sulfinic Acids - chemistry Sulfinic Acids - metabolism Sulfonamides - chemistry Sulfonamides - metabolism
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