Issue 3, 2023

Development of an o-aminoanilide-mediated native chemical ligation-assisted DADA strategy for the synthesis of disulfide surrogate peptides

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.

Graphical abstract: Development of an o-aminoanilide-mediated native chemical ligation-assisted DADA strategy for the synthesis of disulfide surrogate peptides

Supplementary files

Article information

Article type
Paper
Submitted
27 Oct 2022
Accepted
11 Dec 2022
First published
12 Dec 2022

Org. Biomol. Chem., 2023,21, 533-537

Development of an o-aminoanilide-mediated native chemical ligation-assisted DADA strategy for the synthesis of disulfide surrogate peptides

T. Cui, W. Li, J. Chen, R. Zhao and Y. Li, Org. Biomol. Chem., 2023, 21, 533 DOI: 10.1039/D2OB01966C

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