title: N-azidoacetylmannosamine-mediated chemical tagging of gangliosides.
abstract: Peracetylated N-alpha-azidoacetylmannosamine (Ac(4)ManNAz) is metabolized by cells to CMP-azidosialic acid. It has been demonstrated previously that in this way azidosialic acid-containing glycoproteins are formed that can be labeled on the cell surface by a modified Staudinger ligation. Here, we first demonstrate that the same procedure also results in the formation of azidosialic acid-containing gangliosides. Deoxymannojirimycin, an inhibitor of N-glycan processing in proteins, decreases the total cell surface labeling in Jurkat cells by approximately 25%. Inhibition of ganglioside biosynthesis with N-[5-(adamantan-1-yl-methoxy)-pentyl]1-deoxynojirimycin reduces cell surface labeling by approximately 75%. In conclusion, exposure of cells to Ac(4)ManNAz allows in vivo chemical tagging of gangliosides.
authors: Department of Biochemistry, Academic Medical Center, University of Amsterdam, 1105 AZ Amsterdam, The Netherlands.
authors: Anton P
authors: AP
authors: Bussink
authors: Paul F
authors: PF
authors: van Swieten
authors: Karen
authors: K
authors: Ghauharali
authors: Saskia
authors: S
authors: Scheij
authors: Marco
authors: M
authors: van Eijk
authors: Tom
authors: T
authors: Wennekes
authors: Gijs A
authors: GA
authors: van der Marel
authors: Rolf G
authors: RG
authors: Boot
authors: Johannes M F G
authors: JM
authors: Aerts
authors: Herman S
authors: HS
authors: Overkleeft
mesh_terms: D017485:1-Deoxynojirimycin / Q000494:pharmacology; D001386:Azides / Q000737:chemistry / Q000378:metabolism*; D050260:Carbohydrate Metabolism / Q000187:drug effects; D005732:Gangliosides / Q000737:chemistry / Q000378:metabolism*; D006023:Glycoproteins / Q000737:chemistry / Q000378:metabolism; D006595:Hexosamines / Q000737:chemistry / Q000378:metabolism*; D006801:Humans; D019169:Jurkat Cells; D009844:Oligosaccharides / Q000737:chemistry / Q000378:metabolism
chemical_list: D001386:Azides; D005732:Gangliosides; D006023:Glycoproteins; D006595:Hexosamines; C405953:N-azidoacetylmannosamine; D009844:Oligosaccharides; D017485:1-Deoxynojirimycin