Effect of the #alpha#-Methyl Substituent on Chemoselectivity in Esterase-Catalyzed Hydrolysis of S-Acetyl Sulfanylalkanoates

摘要

The isomeric compounds 1 and 3, which differ only in the position of a methyl substituent, give opposite chemoselectivities in an esterase-catalyzed hydrolysis reaction. The esterase was chemoselective for the oxoester in 1, but for the thiol ester group in 3. A high enantioselectivity was observed for both 1 and 3.