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Molecules 2013, 18(6), 7145-7159; doi:10.3390/molecules18067145
Review

Applications of Azide-Based Bioorthogonal Click Chemistry in Glycobiology

 and
*
Ministry of Education Key Laboratory of Systems Biomedicine, Shanghai Center for Systems Biomedicine (SCSB), Shanghai Jiao Tong University, 800 Dong Chuan Road, Minhang, Shanghai 200240, China
* Author to whom correspondence should be addressed.
Received: 20 May 2013 / Revised: 12 June 2013 / Accepted: 14 June 2013 / Published: 19 June 2013
(This article belongs to the Special Issue Advances in Click Chemistry)
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Abstract

Click chemistry is a powerful chemical reaction with excellent bioorthogonality features: biocompatible, rapid and highly specific in biological environments. For glycobiology, bioorthogonal click chemistry has created a new method for glycan non-invasive imaging in living systems, selective metabolic engineering, and offered an elite chemical handle for biological manipulation and glycomics studies. Especially the [3 + 2] dipolar cycloadditions of azides with strained alkynes and the Staudinger ligation of azides and triarylphosphines have been widely used among the extant click reactions. This review focuses on the azide-based bioorthogonal click chemistry, describing the characteristics and development of these reactions, introducing some recent applications in glycobiology research, especially in glycan metabolic engineering, including glycan non-invasive imaging, glycomics studies and viral surface manipulation for drug discovery as well as other applications like activity-based protein profiling and carbohydrate microarrays.
Keywords: click chemistry; azide; bioorthogonal; glycosylation; glycobiology click chemistry; azide; bioorthogonal; glycosylation; glycobiology
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Zhang, X.; Zhang, Y. Applications of Azide-Based Bioorthogonal Click Chemistry in Glycobiology. Molecules 2013, 18, 7145-7159.

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