Synthesis of 4-(1,2,3-triazol-1-yl)-L-phenylalanines

Abstract

Synthesis of a new structural class of phenylalanine derivatives is described. Azidonation of Boc-L-Phe(4-I)-OMe via copper-ligand catalysis with sodium azide under microwave irradiation followed by regioselective copper-catalyzed azide-terminal alkyne cycloaddition provided new 4-(1,2,3-triazol-1-yl)-L-Phe derivatives. The developed protocol was also successfully employed to synthesize a late-stage modified Phe containing peptide.

Graphical Abstract

Keywords:

• Azidonation
• cycloaddition
• peptides
• phenylalanine

Acknowledgments

Nitin Bagra thanks the National Institute for Pharmaceutical Education and Research, S.A.S. Nagar, Punjab, India for the award of Junior and Senior Research Fellowship.

Disclosure statement

No potential conflict of interest was reported by the author(s).