Thioproline-Based Oxidation Strategy for Direct Preparation of N-Terminal Thiazolidine-Containing Peptide Thioesters from Peptide Hydrazides.
Org Lett
; 26(23): 5021-5026, 2024 Jun 14.
Article
in En
| MEDLINE
| ID: mdl-38842216
ABSTRACT
We describe a simple and robust oxidation strategy for preparing N-terminal thiazolidine-containing peptide thioesters from peptide hydrazides. We find for the first time that l-thioproline can be used as a protective agent to prevent the nitrosation of N-terminal thiazolidine during peptide hydrazide oxidation. The thioproline-based oxidation strategy has been successfully applied to the chemical synthesis of CC chemokine ligand-2 (69aa) and omniligase-C (113aa), thereby demonstrating its utility in hydrazide-based native chemical ligation.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Oxidation-Reduction
/
Peptides
/
Thiazolidines
Language:
En
Journal:
Org Lett
Journal subject:
BIOQUIMICA
Year:
2024
Document type:
Article
Country of publication:
United States