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Applications of Azide-Based Bioorthogonal Click Chemistry in Glycobiology
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; in revised form: 12 June 2013 / Accepted: 14 June 2013 / Published: 19 June 2013
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
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MDPI and ACS Style
Zhang, X.; Zhang, Y. Applications of Azide-Based Bioorthogonal Click Chemistry in Glycobiology. Molecules 2013, 18, 7145-7159.
Zhang X, Zhang Y. Applications of Azide-Based Bioorthogonal Click Chemistry in Glycobiology. Molecules. 2013; 18(6):7145-7159.
Zhang, Xiu; Zhang, Yan. 2013. "Applications of Azide-Based Bioorthogonal Click Chemistry in Glycobiology." Molecules 18, no. 6: 7145-7159.