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Exploiting azido-dichloro-triazine as a linker for regioselective incorporation of peptides through their N, O, S functional groups

Abstract:

In the field of bioconjugation, linker development has witnessed massive growth in recent years. 2,4,6-Trichloro-1,3,5-triazine (TCT) is a tridentate linker that can accommodate three distinct nucleophiles. Herein, the reaction of azido triazine derivatives with nucleophiles (amine, thiol and phenol) is studied. The replacement of first chlorine was performed at 0 °C while that of the last chlorine was achieved successfully at rt. As a proof of concept of this strategy with potential application in biological studies, pentapeptides (Ac-XGGFL-NH2 where X = Lys or Tyr or Cys) were reacted with 2-azido-4,6-dichlorotriazine to replace the first and second chlorine at 0 °C and at rt, respectively. The reactivity of 2-azido-4,6-dichlorotriazine was found to be similar for the α and ε amine group present in same peptide. These findings demonstrate the applicability of 2-azido-4,6-dichlorotriazine as a linker with potential further application in bioconjugation.