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.
Highlights
Glycosylation, the most complex and ubiquitous post-translational modification, is involved in a number of physiological and pathological processes
Building upon the features of azide-alkyne cycloaddition, the inert coupling partners enable the reporter to attach the probe after enzymes have been labeled and achieve the identification of targets of enzyme activities expressed in living systems
The exquisite selectivity and biocompatibility of bioorthogonal click chemistry render it a valuable chemical approach for biological research. In glycobiology, it has brought about a fundamental revolution in glycan imaging and metabolic engineering
Summary
Glycosylation, the most complex and ubiquitous post-translational modification, is involved in a number of physiological and pathological processes. The chemical technologies are able to overcome the chemical similarity and structural complexity of glycoconjugates Among all those chemical tools, the bio-orthogonal reagents of click chemistry have demonstrated unique advantages: bioorthogonality, biocompatibility, high efficiency and high specificity. Prescher and Bertozzi defined bioorthogonal click chemical reporters as ―non-native, non-perturbing chemical handles that can be modified in living systems through highly selective reactions with exogenously delivered probes ‖ [4]. During the development of glycobiology, the most influential and most widely used bioorthogonal click reagent is azide, a rather small molecule with attractive bio-stability and non-perturbation ability. It can modify proteins, and all classes of biomolecules, including nucleotides, lipids, and glycans, as well as other metabolites. Azide more than just plays a role as the bioorthogonal chemical reporter, it can be an elite glycan handle applied to various glycobiology research topics
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
