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Peptide Alkyl Thioester Synthesis from Advanced Thiols and Peptide Hydrazides
Journal article   Open access   Peer reviewed

Peptide Alkyl Thioester Synthesis from Advanced Thiols and Peptide Hydrazides

Julie Di Adamo, Nathalie Ollivier, Sonia Cantel, Vincent Diemer and Oleg Melnyk
Journal of Organic Chemistry, Vol.89(18), pp.13719-13724
20/05/2024
PMID: 39257180

Abstract

Peptide Thioester Hydrazide Aryl thiol Alkyl thiol Thiol-thioester exchange Sodium nitrite Acyl azide Coenzyme A Chemical Protein Synthesis Equilibrium displacement Liquid-liquid extraction Sulfhydryl Compounds Peptides Esters Hydrazines Molecular Structure
Peptide alkyl thioesters are versatile reagents in various synthetic applications, commonly generated from peptide hydrazides and thiols. However, a notable limitation is the need for a substantial excess of the thiol reagent, restricting the usage to simple thiols. Here, we introduce an adapted procedure that significantly enhances thioester production with just a minimal thiol excess, facilitating the use of advanced thiol nucleophiles.
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