The Cu-I-catalyzed alkyne-azide cycloaddition as direct conjugation/cyclization method of peptides to steroids

Autor(es)

Echemendia, Radell ^[1] ; Concepcion, Odette ^{[2, 1]} ; Morales, Fidel E. ^[1] ; Paixao, Marcio W. ^[2] ; Rivera, Daniel G. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Havana, Fac Chem, Ctr Nat Prod Study, Havana 10400 - Cuba

^[2] Univ Fed Sao Carlos, Dept Quim, BR-97105900 Sao Carlos, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Tetrahedron; v. 70, n. 20, p. 3297-3305, MAY 20 2014.
• Citações Web of Science: 13

Resumo

The Cu-I-catalyzed azide-alkyne 1,3-dipolar cycloaddition is implemented as a direct conjugation method of alkynyl peptides to azidosteroids, enabling the preparation of novel triazole-linked peptide steroid conjugates in good to excellent yields. The process comprised the solution-phase synthesis of oligopeptides featuring varied chain length and amino acid sequence as well as the preparation of a small library of azidosteroids bearing the azido group either at the side chain or the steroidal nucleus. An alternative strategy relying on a sequential peptide coupling/CuAAC-based macrocyclization procedure was also developed to afford macrocyclic peptide steroid conjugates featuring different sizes and topologies. Both methods showed great chemical efficiency and versatility, thus showing promise toward the future preparation of conjugates with potential pharmaceutical and biological applications. (C) 2013 Published by Elsevier Ltd. (AU)

• Processo FAPESP: 09/07281-0 - Organocatálise assimétrica: preparação de novos organocatalisadores e desenvolvimento de novas metodologias
• Beneficiário: Márcio Weber Paixão
• Modalidade de apoio: Auxílio à Pesquisa - Jovens Pesquisadores