Synthesis of Tripeptide

Let us try the synthesis a tripeptide having Phe-Gly-Ala sequence. Coupling of Fmoc-glycine to the free amino group of t-butyl protected alanine could be effected by the reagent 1,3-dicyclohexylcarbodiimide (DCC) in the presence of N-hyroxysuccinimide (NHS). DCC is converted into DCU. The resulting protected dipipetide could be deproteced using piperdine and coupled with Fmoc-phenylalanine to give the protected tripeptide Fmoc-Phe-Gly-Ala- t Bu. The protecting groups could be deprotected using weak base (Fmoc) and mild acid ( t Bu) to afford the target peptide, Phe-Gly-Ala.

The Role of DCC and NHS in Peptide Synthesis