Journal
SYNTHETIC COMMUNICATIONS
Volume 52, Issue 8, Pages 1176-1183Publisher
TAYLOR & FRANCIS INC
DOI: 10.1080/00397911.2022.2077114
Keywords
Azidonation; cycloaddition; peptides; phenylalanine
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Funding
- National Institute for Pharmaceutical Education and Research, S.A.S. Nagar, Punjab, India
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A new structural class of phenylalanine derivatives was synthesized using copper-ligand catalysis and microwave irradiation. The developed protocol enabled the efficient synthesis of the target products through regioselective copper-catalyzed azide-terminal alkyne cycloaddition.
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.
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