Fmoc Solid-Phase Synthesis of C-Terminal Peptide Thioesters by Formation of a Backbone Pyroglutamyl Imide Moiety

被引：61

作者：

Tofteng, A. Pernille ^{[1
]}

Sorensen, Kasper K. ^{[1
]}

Conde-Frieboes, Kilian W.

Hoeg-Jensen, Thomas

Jensen, Knud J. ^{[1
]}

机构：

[1] Univ Copenhagen, Fac Life Sci, IGM, DK-1871 Frederiksberg, Denmark

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 40期

关键词：

amide activation; nucleophilic substitution; peptides; solid-phase synthesis; thioesters; NATIVE CHEMICAL LIGATION; GENERATION; ACTIVATION; PROTEINS; ESTERS; SHIFT; ACIDS;

D O I：

10.1002/anie.200903710

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Activating an inactive bond: A new concept in synthetic peptide chemistry, backbone amide activation, proceeds through the selective conversion of a backbone amide into an imide, followed by nucleophilic acyl displacement (see scheme; Boc=tert-butoxycarbonyl, Pg=protecting group). This methodology represents a new approach to solidphase synthesis of C-terminal peptide thioesters, and may become a general tool for the synthesis of peptide thioesters. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：7411 / 7414

页数：4

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