The separations by reversed phase high‐performance liquid chromatography on a μBondapak‐C18 column of 53 epimeric N‐substituted di‐, tri‐ and tetrapeptide acids and esters have been attempted, with success in three quarters of the cases. Substituents include acetyl, benzoyl, benzyloxycarbonyl, tert.‐butoxycarbonyl and 9‐fluorenylmethoxycarbonyl. The series N‐benzyloxycarbonylglycyl‐Xxx‐valine ethyl ester with Xxx = alanyl, valyl, leucyl and phenylalanyl, is recommended for use in studies on racemization. Results on racemization attending the coupling of an amino acid ester as compared with a di‐ and tripeptide ester vary with the coupling method.
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Benoiton et al. (1988) studied this question.
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