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Diazaborine-Mediated Bicyclization of Native Peptides with Inducible Reversibility.
Reja, Rahi M; Chau, Brittney; Gao, Jianmin.
Afiliação
  • Reja RM; Department of Chemistry, Boston College, 2609 Beacon Street, Chestnut Hill, Massachusetts 02467, United Sates.
  • Chau B; Department of Chemistry, Boston College, 2609 Beacon Street, Chestnut Hill, Massachusetts 02467, United Sates.
  • Gao J; Department of Chemistry, Boston College, 2609 Beacon Street, Chestnut Hill, Massachusetts 02467, United Sates.
Org Lett ; 25(24): 4489-4492, 2023 06 23.
Article em En | MEDLINE | ID: mdl-37306633
Multicyclic peptides are appealing candidates for peptide-based drug discovery. While various methods are developed for peptide cyclization, few allow multicyclization of native peptides. Herein we report a novel cross-linker DCA-RMR1, which elicits facile bicyclization of native peptides via N-terminus Cys-Cys cross-linking. The bicyclization is fast, affords quantitative conversion, and tolerates various side chain functionalities. Importantly, the resulting diazaborine linkage, while stable at a neutral pH, can readily reverse upon mild acidification to give pH-responsive peptides.
Assuntos

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Peptídeos / Peptídeos Cíclicos Idioma: En Revista: Org Lett Assunto da revista: BIOQUIMICA Ano de publicação: 2023 Tipo de documento: Article

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Peptídeos / Peptídeos Cíclicos Idioma: En Revista: Org Lett Assunto da revista: BIOQUIMICA Ano de publicação: 2023 Tipo de documento: Article