Synthesis of Tripeptide

Scheme 5 illustrates the synthesis of Gly-Phe-Ala sequence. The condensation of the Fmoc-phenylalanine with t-butyl protected alanine using 1,3-dicyclohexylcarbodiimide (DCC)  and N-

 

hyroxysuccinimide (NHS) can give the protected dipeptide, Fmoc-Phe-Ala-^tBu. The latter, after Fmoc deprotection using piperdine, can be coupled with Fmoc-glycine to give the protected tripeptide Fmoc-Gly-Phe-Ala-^tBu. The protecting groups can be then deprotected using weak base (Fmoc) and mild acid (^tBu) to afford the target tripeptide, Gly-Phe-Ala.

The Role of DCC and NHS in Peptide Synthesis