Development of an o-aminoanilide-mediated native chemical ligation-assisted DADA strategy for the synthesis of disulfide surrogate peptides. Issue 3 (19th December 2022)

• Record Type: Journal Article
• Authors: Cui, Tingting; Li, Wen-Jie; Chen, Junyou; Zhao, Rui; Li, Yi-Ming
• Is Part Of: Organic & biomolecular chemistry. Volume 21:Issue 3(2023)
• Page Start: 533
• Page End: 537
• Publication Date: 2022-12-19
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob01966c
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Herein, we report a peptide o -aminoanilide-mediated NCL-assisted DADA strategy for the synthesis of large-span active peptide disulfide bridge surrogates containing only Gln–Cys or Asn–Cys ligation sites. Abstract : The hydrazide-based native chemical ligation-assisted diaminodiacid (DADA) strategy is an efficient method for synthesizing large-span disulfide bridge surrogates. However, it is difficult to synthesize disulfide bond surrogates at Gln–Cys or Asn–Cys ligation sites using this strategy. Herein, we report a peptide o -aminoanilide-mediated NCL-assisted DADA strategy that enables the synthesis of large-span peptide disulfide bridge surrogates containing only Gln–Cys or Asn–Cys ligation sites. Through this strategy, we successfully synthesized disulfide bond surrogates of conotoxin vil14a and κ-hefutoxin 1. This strategy provides a new option to obtain large-span peptide disulfide bridge substitutes for native chemical ligation at Gln–Cys and Asn–Cys sites.