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Originally published In Press as doi:10.1194/jlr.C700006-JLR200 on March 27, 2007

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Journal of Lipid Research, Vol. 48, 1417-1421, June 2007
Copyright © 2007 by American Society for Biochemistry and Molecular Biology

Methods

N-Azidoacetylmannosamine-mediated chemical tagging of gangliosides

Anton P. Bussink1,*, Paul F. van Swieten1,{dagger}, Karen Ghauharali*, Saskia Scheij*, Marco van Eijk*, Tom Wennekes{dagger}, Gijs A. van der Marel{dagger}, Rolf G. Boot*, Johannes M. F. G. Aerts2,* and Herman S. Overkleeft2,{dagger}

* Department of Biochemistry, Academic Medical Center, University of Amsterdam, 1105 AZ Amsterdam, The Netherlands
{dagger} Leiden Institute of Chemistry, Leiden University, 2300 RA Leiden, The Netherlands

Published, JLR Papers in Press, March 27, 2007.

1 A. P. Bussink and P. F. van Swieten contributed equally to this work.

2 To whom correspondence should be addressed. e-mail: j.m.aerts{at}amc.uva.nl (J.M.F.G.A.); h.s.overkleeft{at}chem.leidenuniv.nl (H.S.O.)

Peracetylated N-{alpha}-azidoacetylmannosamine (Ac4ManNAz) 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 ~25%. Inhibition of ganglioside biosynthesis with N-[5-(adamantan-1-yl-methoxy)-pentyl]1-deoxynojirimycin reduces cell surface labeling by ~75%. In conclusion, exposure of cells to Ac4ManNAz allows in vivo chemical tagging of gangliosides.

Supplementary key words N-acetylmannosamine • iminosugar • azide • Staudinger ligation • sialic acid • chemical ligation • cell surface labeling


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