A New Method for Synthesis of Peptide Thioesters via Irreversible N-to-S Acyl Transfer

被引：16

作者：

Zheng, Ji-Shen ^{[1
,3
]}

Chen, Xin ^{[2
]}

Tang, Shan ^{[2
,3
]}

Chang, Hao-Nan ^{[3
]}

Wang, Feng-Liang ^{[3
]}

Zuo, Chao ^{[3
]}

机构：

[1] Chinese Acad Sci, High Field Magnet Lab, Hefei 230031, Peoples R China

[2] Tsinghua Univ, Tsinghua Peking Ctr Life Sci, Beijing 100084, Peoples R China

[3] Tsinghua Univ, Dept Chem, Beijing 100084, Peoples R China

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 18期

关键词：

SOLID-PHASE SYNTHESIS; TANDEM THIOL SWITCH; CHEMICAL-SYNTHESIS; LIGATION; PROTEINS; SEMISYNTHESIS; GLYCOPROTEIN; ACTIVATION; GENERATION; CLEAVAGE;

D O I：

10.1021/ol5024213

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new synthetic method for peptide thioesters is described using Fmoc solid-phase peptide synthesis (Fmoc-SPPS). This method employs a novel enamide motif to facilitate irreversible intramolecular N-to-S acyl migration, which can efficiently afford the desired peptide thioesters (3 h, 30 degrees C) under the final trifluoroacetic acid (TFA) cleavage conditions. The acyl-transfer-mediated approach for synthesis of peptide thioesters tolerated different C-terminal residues and was used to synthesize human C C motif chemokine 11 (hCCL11) via native chemical ligation.

引用

页码：4908 / 4911

页数：4

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