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A more recent version of this article appeared on June 1, 2007

Papers In Press, published online ahead of print March 27, 2007
J. Lipid Res., doi:10.1194/jlr.C700006-JLR200
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Submitted on February 21, 2007
Revised on March 26, 2007
Accepted on March 26, 2007

N-Azidoacetylmannosamine mediated chemical tagging of gangliosides

Anton P. Bussink, Paul F. van Swieten, Karen Ghauharali, Saskia Scheij, Marco van Eijk, Tom Wennekes, Gijs A. van der Marel, Rolf G. Boot, Johannes M.F.G. Aerts, and Herman S. Overkleeft

Medical Biochemistry, Academic Medical Centre, Amsterdam, Noord-Holland 1105 AZ

Corresponding Author: j.m.aerts{at}amc.uva.nl

Peracetylated N-alpha -azidoacetylmannosamine is metabolized by cells to CMP-azidosialic acid. It has earlier been demonstrated that in this way azidosialic acid-containing glycoproteins are formed that can be labeled on the cell surface by a modified Staudinger ligation. We here firstly demonstrate that the same procedure also results in formation of azidosialic acid-containing gangliosides. Deoxymannojirimycin, an inhibitor of N-glycan processing in proteins, lowers by about 25% the total cell surface labeling in Jurkat cells. Inhibition of ganglioside biosynthesis with N-(adamantanemethyloxy)pentyl-deoxynojirimycin reduces by about 75% cell surface labeling. In conclusion, exposure of cells to peracetylated N-alpha -azidoacetylmannosamine allows in vivo chemical tagging of gangliosides.


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