Potential d,l -Amino Acid Sequence Analysis of Peptides from the C-Terminus

A model tripeptide, Gly-L-Leu-L-Phe, was immobilized with activated aminomethyl polystyrene, and its C-terminal was reduced to an alcohol. This peptidyl alcohol was selectively hydrolyzed at the C-terminal amide bond to afford a polymer-supported dipeptide (Gly-L-Leu) and amino alcohol (Phe-OH). The amino alcohol, including its absolute configuration, was determined by labelling with (+)-MNB-COOH, and the dipeptide was reused for a determination of its C-terminal amino acids. The d, l-amino acids of the tripeptide were sequentially determined from the C-terminus.