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; Herman S. Overkleeft

doi:10.1194/jlr.C700006-JLR200

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, Herman S. Overkleeft^*

^*Corresponding author for this work

Leiden University

Research output: Contribution to journal › Article › Academic › peer-review

Abstract

Peracetylated N-α-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.

Original language	English
Pages (from-to)	1417-1421
Journal	Journal of Lipid Research
Volume	48
Issue number	6
DOIs	https://doi.org/10.1194/jlr.C700006-JLR200
Publication status	Published - 2007
Externally published	Yes

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@article{c627198614ef4b26a52840846651f931,

title = "N-Azidoacetylmannosamine-mediated chemical tagging of gangliosides",

abstract = "Peracetylated N-α-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.",

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

year = "2007",

doi = "10.1194/jlr.C700006-JLR200",

language = "English",

volume = "48",

pages = "1417--1421",

journal = "Journal of Lipid Research",

issn = "0022-2275",

publisher = "American Society for Biochemistry and Molecular Biology Inc.",

number = "6",

}

TY - JOUR

T1 - N-Azidoacetylmannosamine-mediated chemical tagging of gangliosides

AU - Bussink, Anton P.

AU - van Swieten, Paul F.

AU - Ghauharali, Karen

AU - Scheij, Saskia

AU - van Eijk, Marco

AU - Wennekes, Tom

AU - van der Marel, Gijs A.

AU - Boot, Rolf G.

AU - Aerts, Johannes M. F. G.

AU - Overkleeft, Herman S.

PY - 2007

Y1 - 2007

N2 - Peracetylated N-α-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.

AB - Peracetylated N-α-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.

U2 - 10.1194/jlr.C700006-JLR200

DO - 10.1194/jlr.C700006-JLR200

M3 - Article

SN - 0022-2275

VL - 48

SP - 1417

EP - 1421

JO - Journal of Lipid Research

JF - Journal of Lipid Research

IS - 6

ER -

N-Azidoacetylmannosamine-mediated chemical tagging of gangliosides

Abstract

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