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Protein N-glycosylation is an active area of research in chemical biology. This chapter highlights several chemical biological approaches to deciphering protein N-glycosylation. These include: the use of specific inhibitors of N-glycan-processing enzymes for controlling N-glycosylation; the design of metabolic and mechanism-based inhibitors for modulating global sialylation and fucosylation of cell-surface glycoproteins and for combating influenza; the exploitation of glycan metabolic engineering for labeling and probing cell-surface glycosylation; and selected chemoenzymatic approaches to glycan remodeling of glycoproteins for making homogeneous glycoproteins. In particular, the ability to produce homogeneous glycoproteins either by the use of specific enzyme inhibitors during recombinant production or by chemoenzymatic glycan remodeling provides exciting opportunities to probe in more details the structure and function of glycoproteins and to develop glycoprotein-based therapeutics.

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