Incorporation of the hexose analogue 2-deoxy-d-galactose into membrane glycoproteins in HepG2 cells

Geilen, Christoph C.; Kannicht, Christoph; Orthen, Bruno; Heidrich, Claudia; Paul, Christine; Grunow, Detlef; Nuck, Rolf; Reutter, Werner

doi:10.1016/0003-9861(92)90551-7

Cited by 8 publications

(7 citation statements)

References 24 publications

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“…This is in accordance with recent findings on 2dGal incorporation into membrane glycoproteins of our group [3]. In the study, we have shown that only 10% of the galactose residues of glycoproteins were replaced by 2dGal.…”

Section: Start -supporting

confidence: 94%

“…ZdGal-modified G,,, is composed of o-glucose, 2dGal and N-acetyl-neuraminic acid. We suggest the possible substitution of the g&lactose residue by a 2dGal residue as shown earlier studies we used different approaches to demonstrate that 2dGal is incorporated into the oligosaccharide moiety of membrane giycoproteins [2,3]. These findings are in agreement with data on the metabolism of 2dGa1, which indicated the formation of UDP-2-deoxy-D-galactose.…”

Section: Start -supporting

confidence: 90%

“…Our data show for the first time that 2dGal is incorporated into G,,, Go,, Go,, and G,,,. The incorporation of 2dGal into gangliosides was higher as compared to the incorporation of 2dGal into glycoproteins [3].…”

Section: Introductionmentioning

confidence: 76%

“…For quantitative analysis a Carlo Erba HRCG 5300 gas chromatograph, equipped with flame ionisation detection (FID), was used as described earlier [3]. Samples were analysed on a DB210-30N capillary column (J&W Scientific, Ranch0 Cordova, USA) by on-column injection and on a DBl-60N capillary column (J&W Scientific, Ranch0 Cordova.…”

Section: Caprllary Gas Liqutd Chromatography Mass Spectrometry (Glcimentioning

confidence: 99%

“…Recently, using GLCI MS analysis, we demonstrated that 2dGal is incorporated into the oligosaccharide moiety of membrane glycoproteins of HepG2 cells. The incorporation of 2dGal was paralleled by a reduced al-2 fucosylation [3].…”

Section: Introductionmentioning

confidence: 98%

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Synthesis of 2‐deoxy‐d‐galactose containing gangliosides in vivo

et al. 1993

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Incorporationof 2-deoxy-o-galactose into the oligosaccharide moieties of different gangliosides of rat liver was examined. After intraperitoneal administration of 2-deoxy-n-galactose it was shown by GLC/MS analysis that this hexose analogue is metabolized and incorporated into all the ganghosides investigated. and predommantly mto G,, and G,,. In both of these gangliosides. 25-55% of the galactose residues were substituted by 2-deoxy-n-galactose.The epimer, 2-deoxy-n-glucose, was not detectable.

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Section: Start -supporting

confidence: 94%

Section: Start -supporting

confidence: 90%

Section: Introductionmentioning

confidence: 76%

Section: Caprllary Gas Liqutd Chromatography Mass Spectrometry (Glcimentioning

confidence: 99%

Section: Introductionmentioning

confidence: 98%

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Synthesis of 2‐deoxy‐d‐galactose containing gangliosides in vivo

et al. 1993

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Glycosyltransferases

Williams¹

2009

Carbohydrates: The Essential Molecules of Life

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Biosynthetic Modulation of Sialic Acid-dependent Virus-Receptor Interactions of Two Primate Polyoma Viruses

Keppler

Stehling

Herrmann

et al. 1995

Journal of Biological Chemistry

169

145

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Sialic acids are essential components of the cell surface receptors of many microorganisms including viruses. A synthetic, N-substituted D-mannosamine derivative has been shown to act as precursor for structurally altered sialic acid incorporated into glycoconjugates in vivo (Kayser, H., Zeitler, R., Kannicht, C., Grunow, D., Nuck, R., and Reutter, W. (1992) J. Biol. Chem. 267, 16934-16938). In this study we have analyzed the potential of three different sialic acid precursor analogues to modulate sialic acid-dependent virus receptor function on different cells. We show that treatment with these D-mannosamine derivatives can result in the structural modification of about 50% of total cellular sialic acid content. Treatment interfered drastically and specifically with sialic acid-dependent infection of two distinct primate polyoma viruses. Both inhibition (over 95%) and enhancement (up to 7-fold) of virus binding and infection were observed depending on the N-acyl substitution at the C-5 position of sialic acid. These effects were attributed to the synthesis of metabolically modified, sialylated virus receptors, carrying elongated N-acyl groups, with altered binding affinities for virus particles. Thus, the principle of biosynthetic modification of sialic acid by application of appropriate sialic acid precursors to tissue culture or in vivo offers new means to specifically influence sialic acid-dependent ligand-receptor interactions and could be a potent tool to further clarify the biological functions of sialic acid, in particular its N-acyl side chain.

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Incorporation of the hexose analogue 2-deoxy-d-galactose into membrane glycoproteins in HepG2 cells

Cited by 8 publications

References 24 publications

Synthesis of 2‐deoxy‐d‐galactose containing gangliosides in vivo

Synthesis of 2‐deoxy‐d‐galactose containing gangliosides in vivo

Glycosyltransferases

Biosynthetic Modulation of Sialic Acid-dependent Virus-Receptor Interactions of Two Primate Polyoma Viruses

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