title: Metabolic labeling of glycans with azido sugars for visualization and glycoproteomics.
abstract: The staggering complexity of glycans renders their analysis extraordinarily difficult, particularly in living systems. A recently developed technology, termed metabolic oligosaccharide engineering, enables glycan labeling with probes for visualization in cells and living animals, and enrichment of specific glycoconjugate types for proteomic analysis. This technology involves metabolic labeling of glycans with a specifically reactive, abiotic functional group, the azide. Azido sugars are fed to cells and integrated by the glycan biosynthetic machinery into various glycoconjugates. The azido sugars are then covalently tagged, either ex vivo or in vivo, using one of two azide-specific chemistries: the Staudinger ligation, or the strain-promoted [3+2] cycloaddition. These reactions can be used to tag glycans with imaging probes or epitope tags, thus enabling the visualization or enrichment of glycoconjugates. Applications to noninvasive imaging and glycoproteomic analyses are discussed.
authors.affiliation: Department of Chemistry, Howard Hughes Medical Institute, University of California, Berkeley, USA.
authors.forename: Scott T
authors.initials: ST
authors.lastname: Laughlin
authors.forename: Nicholas J
authors.initials: NJ
authors.lastname: Agard
authors.forename: Jeremy M
authors.initials: JM
authors.lastname: Baskin
authors.forename: Isaac S
authors.initials: IS
authors.lastname: Carrico
authors.forename: Pamela V
authors.initials: PV
authors.lastname: Chang
authors.forename: Anjali S
authors.initials: AS
authors.lastname: Ganguli
authors.forename: Matthew J
authors.initials: MJ
authors.lastname: Hangauer
authors.forename: Anderson
authors.initials: A
authors.lastname: Lo
authors.forename: Jennifer A
authors.initials: JA
authors.lastname: Prescher
authors.forename: Carolyn R
authors.initials: CR
authors.lastname: Bertozzi
mesh_terms: D000818:Animals; D001386:Azides / Q000737:chemistry* / Q000378:metabolism; D002236:Carbohydrate Conformation; D002478:Cells, Cultured; D006023:Glycoproteins / Q000737:chemistry / Q000378:metabolism; D007202:Indicators and Reagents / Q000737:chemistry*; D051379:Mice; D008969:Molecular Sequence Data; D015394:Molecular Structure; D011134:Polysaccharides / Q000737:chemistry / Q000378:metabolism; D020543:Proteome / Q000032:analysis*; D040901:Proteomics / Q000379:methods*
chemical_list: D001386:Azides; D006023:Glycoproteins; D007202:Indicators and Reagents; D011134:Polysaccharides; D020543:Proteome