Kinetics of aminolysis for 1-thio-β- D-glucopyranosyl esters of N-acylalanines

The kinetics of aminolysis of 1-thio-β-D-glucopyranosyl esters of N-protected alanines (1) in dichloromethane, at 26°, by ethyl glycinate, under pseudo-first-order conditions follows the relationship k-_obsd = k₂[H-Gly-OEt]. Significant differences were observed in the rates of dipeptide forming aminolysis for 1-thiolesters 1a-1f, depending on N-acyl substituents and the configuration of alanine.