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An amine-derivatized DOTA has been used to modify the surface of a polymeric support for conventional solid phase peptide synthesis (SPPS) following standard Fmoc chemistry methods. This methodology was used to synthesize a peptide–DOTA conjugate that was demonstrated to be a PARACEST MRI contrast agent. Therefore, this synthesis methodology can facilitate Fmoc SPPS of molecular imaging contrast agents.
An amino group has been introduced into one ligand of DOTA that can couple to peptidyl carboxylates by coupling α-brominated glycine to DO3A- t Bu (1,4,7,10-tetraazacyclododecane-1,4,7-tris(acetic acid, tert-butylester)). α-Amino-DOTA was coupled to the carboxylate backbone terminus of a peptide to demonstrate the utility for derivatization.
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