A Tripeptide Approach to the Solid-Phase Synthesis of Peptide Thioacids and N-Glycopeptides

被引：8

作者：

Schoewe, Markus Julian ^{[1
]}

Keiper, Odin ^{[1
]}

Unverzagt, Carlo ^{[2
]}

Wittmann, Valentin ^{[1
]}

机构：

[1] Univ Konstanz, Dept Chem, D-78457 Constance, Germany

[2] Univ Bayreuth, Bioorgan Chem, Univ Str 30, D-95447 Bayreuth, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2019年 / 25卷 / 69期

关键词：

bioorganic chemistry; glycopeptides; ligation; solid-phase peptide synthesis; thioacids; CHEMICAL-SYNTHESIS; CARBOHYDRATE;

D O I：

10.1002/chem.201904688

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A general and robust method for the incorporation of aspartates with a thioacid side chain into peptides has been developed. Pseudoproline tripeptides served as building blocks for the efficient fluorenylmethyloxycarbonyl (Fmoc) solid-phase synthesis of thioacid-containing peptides. These peptides were readily converted to complex N-glycopeptides by using a fast and chemoselective one-pot deprotection/ligation procedure. Furthermore, a novel side reaction that can lead to site-selective peptide cleavage using thioacids (CUT) was discovered and studied in detail.

引用

页码：15759 / 15764

页数：6

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