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This chapter describes a straightforward strategy for obtaining peptide salicylaldehyde (SAL) ester surrogates from synthetic or recombinant peptide hydrazides via nitrite oxidation and phenolysis using 3-(1,3-dithian-2-yl)-4-hydroxybenzoic acid (SAL(-COOH)PDT). The process involves the oxidation of peptide hydrazides to peptide azides, followed by phenolysis to form peptide SAL(-COOH)PDT esters, which can then be activated to yield reactive peptide SAL(-COOH) esters. Detailed procedures for the oxidation, phenolysis, and activation steps are provided, along with troubleshooting tips and considerations to ensure successful implementation of the method for serine/threonine ligation (STL) and cysteine/penicillamine ligation (CPL).

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Preparation of Peptide C-Terminal Salicylaldehyde Ester Surrogates via a Hydrazide-Based Oxidation and Phenolysis Strategy

  • 实验方案

  • 发表日期：

    2025年

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  • Shaomin Lin,
  • Chunmao He

摘要

This chapter describes a straightforward strategy for obtaining peptide salicylaldehyde (SAL) ester surrogates from synthetic or recombinant peptide hydrazides via nitrite oxidation and phenolysis using 3-(1,3-dithian-2-yl)-4-hydroxybenzoic acid (SAL(-COOH)PDT). The process involves the oxidation of peptide hydrazides to peptide azides, followed by phenolysis to form peptide SAL(-COOH)PDT esters, which can then be activated to yield reactive peptide SAL(-COOH) esters. Detailed procedures for the oxidation, phenolysis, and activation steps are provided, along with troubleshooting tips and considerations to ensure successful implementation of the method for serine/threonine ligation (STL) and cysteine/penicillamine ligation (CPL).