Sw. Markowicz et J. Karolakwojciechowska, MOLECULAR MODELING AND SYNTHESIS OF BOC-ALA-GLY-OET BY ACTIVE ESTERS WITH TERPENIC HYDROXYIMIDES, Polish Journal of Chemistry, 68(10), 1994, pp. 1973-1981
''Active esters'' of Boc-D-alanine and terpenic derivatives of the suc
cinic acid N-hydroxyimide (2 and 3) react with the Gly-OExHCl in the p
resence of the Et3N yielding optically pure D-dipeptides. As it was de
termined experimentally and also supported by molecular modelling and
energy calculations, the role of terpenic part involves epimerization
of the potentially racemizing part of the substrate to desirable direc
tion.