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C Terminal Modifications

Peptides can be modified at the C terminus. In general, some standard peptide moieties must be accessible in order to be modified: an N-terminal amino group, the amino group of Lys, the thiol group of Cys, the hydroxyl groups of Ser, Thr, and Tyr, the guanidine group of Arg, and the C-terminal carboxyl group.

C-terminal modification reduces overall solubility of the peptide by reducing its overall charges. However, the stability of the peptide could also be increased because the terminal modification generates a closer mimic of the native protein. Therefore, these modifications might increase the biological activity of a peptide and prevent degradation by enzymes.

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N Terminus Modification Structure

Aldehyde peptide

AFC

7-amino-4-(trifluoromethyl)-2-benzopyrone

AMC

7-amino-4-methylcoumarinyl

Cysteamide

(Mercaptoacetamide)

CMK/FMK

Chloro(fuoro)-methylketones

Ester (OMe/ OEt)

pNA

p-Nitroanilide

OSU

OBzl

OtBu

TBzl