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Peptide Alkyl Thioester Synthesis from Advanced Thiols and Peptide Hydrazides.

Authors :
Di Adamo J
Ollivier N
Cantel S
Diemer V
Melnyk O
Source :
The Journal of organic chemistry [J Org Chem] 2024 Sep 20; Vol. 89 (18), pp. 13719-13724. Date of Electronic Publication: 2024 Sep 10.
Publication Year :
2024

Abstract

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.

Details

Language :
English
ISSN :
1520-6904
Volume :
89
Issue :
18
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
39257180
Full Text :
https://doi.org/10.1021/acs.joc.4c01251