One-Pot Cyclization and Cleavage of Peptides with N-Terminal Cysteine via the N,S-Acyl Shift of the N-2-[Thioethyl]glycine Residue

被引：6

作者：

Wierzbicka, Magdalena ^{[1
]}

Waliczek, Mateusz ^{[1
]}

Dziadecka, Anna ^{[1
]}

Stefanowicz, Piotr ^{[1
]}

机构：

[1] Univ Wroclaw, Fac Chem, PL-50383 Wroclaw, Poland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 17期

关键词：

SOLID-PHASE SYNTHESIS; CYCLIC-PEPTIDES; THIOESTERS; PROTEINS; TRANSAMIDATION; INHIBITOR; COMPLEXES; MIGRATION; LIGATION; LINKER;

D O I：

10.1021/acs.joc.1c01045

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We developed a one-pot method for peptide cleavage from a solid support via the N,S-acyl shift of N-2-[thioethyl]glycine and transthioesterification using external thiols to produce cyclic peptides through native chemical self-ligation with the N-terminal cysteine. The feasibility of this methodology is validated by the syntheses of model short peptides, including a tetrapeptide, the bicyclic sunflower trypsin inhibitor SFTI-1, and rhesus Theta-defensin RTD-1. Synthesis of the whole peptide precursor can be fully automated and proceeds without epimerization or dimerization.

引用

页码：12292 / 12299

页数：8

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