Click Chemistry as a Route to Cyclic Tetrapeptide Analogues: Synthesis of c yclo -[Pro-Val-ψ(triazole)-Pro-Tyr]
2006; American Chemical Society; Volume: 8; Issue: 5 Linguagem: Inglês
10.1021/ol053095o
ISSN1523-7060
AutoresVictoria D. Bock, Rossana Perciaccante, Thomas Paul Jansen, Henk Hiemstra, Jan H. van Maarseveen,
Tópico(s)Monoclonal and Polyclonal Antibodies Research
ResumoDespite the plethora of techniques to cyclize small peptides, a synthesis of cyclo-[(l)Pro-(l)Tyr-(l)Pro-(l)Val], a potent tyrosinase inhibitor, remains elusive because of the unfavorable transition state leading to the cyclic product. Herein, we report the successful synthesis of its triazole analogue, cyclo-[(l)Pro-(l)Val-ψ(triazole)-(l)Pro-(l)Tyr]. Attempted cyclization via peptide bond formation at room temperature fails to provide the desired product, but CuI-catalyzed alkyne-azide coupling at 110 °C affords the triazole tetrapeptide in 70% yield, demonstrating the utility of "click" chemistry.
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