Effect of the alpha-methyl substituent on chemoselectivity in esterase-catalyzed hydrolysis of S-acetyl sulfanylalkanoates.
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.
Kumar
I
I
Department of Chemistry, Institute of Microbial Technology, Chandigarh, India.
Jolly
R S
RS
D002087:Butyrates / Q000737:chemistry*; D002384:Catalysis; D004950:Esterases / Q000737:chemistry*; D006868:Hydrolysis; D011422:Propionates / Q000737:chemistry*; D011551:Pseudomonas fluorescens / Q000737:chemistry; D013237:Stereoisomerism
D002087:Butyrates; D011422:Propionates; C410444:methyl 3-(S-acetylthio)-2-methylpropanoate; C410445:methyl 3-(S-acetylthio)butanoate; D004950:Esterases