Functionalization of protected tyrosine via Sonogashira reaction: synthesis of 3-(1,2,3-triazolyl)-tyrosine.
1,2,3-Triazol tyrosines were synthesized from tyrosine alkynes that were in turn prepared via Sonogashira cross-coupling reaction. The tyrosine alkynes were subjected to click-chemistry reaction conditions leading to the corresponding 3-(1,2,3-triazolyl)-tyrosines in yields ranging from moderate to good.
Departamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, SP, Brasil.
Stanley N S
SN
Vasconcelos
Instituto de Química, Universidade de São Paulo, São Paulo, SP, Brasil.
Anwar
A
Shamim
Departamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, SP, Brasil.
Bakhat
B
Ali
Centro de Engenharia e Ciências Exatas, Universidade Estadual do Oeste do Paraná, Toledo, PR, Brasil.
Isadora M
IM
de Oliveira
Departamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, SP, Brasil. hstefani@usp.br.
Hélio A
HA
Stefani
D000480:Alkynes / Q000737:chemistry; D002384:Catalysis; D057930:Click Chemistry; D014230:Triazoles / Q000737:chemistry*; D014443:Tyrosine / Q000138:chemical synthesis* / Q000737:chemistry*
D000480:Alkynes; D014230:Triazoles; D014443:Tyrosine
Alkyne; Click chemistry; Peptide bond; Triazole; Tyrosine