Structural Factors affecting the kinetics of O,N-acyl transfer in potential O-peptide prodrugs

In the present study, the conversion kinetics of a number of O-peptide prodrugs have been investigated to elucidate the importance of side chain bulkiness, backbone cyclization and the reactive amine moiety. The significant difference in the chemical reactivities of iso[Val-MeLeu (3-OH)-Abu] and iso[Val-Leu (3-OH)-Abu], indicated that the nature of amine moiety is important to the kinetics of O,N-acyl migration. The importance of side chain bulkiness and backbone cyclization were found to be less significant.