Azide: A Unique Dipole for Metal-Free Bioorthogonal Ligations

被引：195

作者：

Debets, Marjoke F. ^{[1
]}

van der Doelen, Christianus W. J. ^{[1
]}

Rutjes, Floris P. J. T. ^{[1
]}

van Delft, Floris L. ^{[1
]}

机构：

[1] Radboud Univ Nijmegen, Inst Mol & Mat, NL-6525 AJ Nijmegen, Netherlands

来源：

CHEMBIOCHEM | 2010年 / 11卷 / 09期

关键词：

azides; bioconjugation; bioorthogonal ligation; cycloaddition; cyclooctynes; metal-free; FREE CLICK CHEMISTRY; COPPER-FREE CLICK; TRACELESS STAUDINGER LIGATION; FREE TRIAZOLE FORMATION; IN-VIVO; 1,3-DIPOLAR CYCLOADDITION; ALKYNE CYCLOADDITION; ESCHERICHIA-COLI; PHOTOCLICK CHEMISTRY; TERMINAL ALKYNES;

D O I：

10.1002/cbic.201000064

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Covalently bound azide on a (small) organic molecule or a (large) biomolecular structure has proven an important handle for bioconjugation. Azides are readily introduced, small, and stable, yet undergo smooth ligation with a range of reactive probes under mild conditions. In particular, the potential of azides to undergo metal-free reactions with strained unsaturated systems has inspired the development of an increasing number of reactive probes, which are comprehensively summarized here. For each individual probe, the synthetic preparation is described, together with reaction kinetics and the full range of applications, from materials science to glycoprofiling. Finally, a qualitative and quantitative comparison of azido-reactive probes is provided.

引用

页码：1168 / 1184

页数：17

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