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Review
Azide: A Unique Dipole for Metal-Free Bioorthogonal Ligations
Article first published online: 7 MAY 2010
DOI: 10.1002/cbic.201000064
Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Debets, M. F., van der Doelen, C. W. J., Rutjes, F. P. J. T. and van Delft, F. L. (2010), Azide: A Unique Dipole for Metal-Free Bioorthogonal Ligations. ChemBioChem, 11: 1168–1184. doi: 10.1002/cbic.201000064
Publication History
- Issue published online: 7 JUN 2010
- Article first published online: 7 MAY 2010
- Manuscript Received: 3 FEB 2010
- Abstract
- Article
- References
- Cited By
Keywords:
- azides;
- bioconjugation;
- bioorthogonal ligation;
- cycloaddition;
- cyclooctynes;
- metal-free
Abstract
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.