Chemistry & Structure

Amidation

Amidation is a chemical modification that replaces the free carboxyl group (-COOH) at a peptide's C-terminus with an amide group (-CONH2). This neutralizes the negative charge of the terminal carboxylate.

C-terminal amidation is widespread in bioactive peptides. Ipamorelin (Aib-His-D-2Nal-D-Phe-Lys-NH2) and MT-II both feature C-terminal amide groups. Many naturally occurring neuropeptides and hormones are also C-terminally amidated.

Amidation can increase resistance to carboxypeptidase degradation and may influence receptor binding. In solid-phase peptide synthesis, amidated peptides are produced using Rink amide resin, which releases the peptide with a C-terminal amide upon cleavage.

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