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  • 1
    Electronic Resource
    Electronic Resource
    Immunosuppressive Activity of Chemically Synthesized Gangliosides (1995)
    s.l. : American Chemical Society
    Biochemistry 34 (1995), S. 1197-1202 
    Details
    ISSN: 1520-4995
    Source: ACS Legacy Archives
    Topics: Biology , Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1021/bi00004a012
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  • 2
    Electronic Resource
    Electronic Resource
    Haemagglutinin mutations responsible for the binding of H5N1 influenza A viruses to human-type receptors (2006)
    [s.l.] : Nature Publishing Group
    Nature 444 (2006), S. 378-382 
    Details
    ISSN: 1476-4687
    Source: Nature Archives 1869 - 2009
    Topics: Biology , Chemistry and Pharmacology , Medicine , Natural Sciences in General , Physics
    Notes: [Auszug] H5N1 influenza A viruses have spread to numerous countries in Asia, Europe and Africa, infecting not only large numbers of poultry, but also an increasing number of humans, often with lethal effects. Human and avian influenza A viruses differ in their recognition of host cell receptors: the ...
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1038/nature05264
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  • 3
    Electronic Resource
    Electronic Resource
    The Structural Basis for the Susceptibility of Gangliosides to Enzymatic Degradation (1999)
    Springer
    Bioscience reports 19 (1999), S. 163-168 
    Details
    ISSN: 1573-4935
    Keywords: Conformation ; gangliosides ; GM2-activator protein ; β-hexosaminiolase ; sialiolase
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The conformational properties of GM2, GalNacβ-4(Neu5Acα-3) Galβ-4Glcβ-1Cer have been compared to those of 6′-GM2, in which the linkage between the GalNAc and Gal was altered from GalNacβ-4Galβ- to GalNacβ-6Galβ-, and to those of GD1a, Neu5Acα-3Galβ-3GalNAcβ-4(Neu5Acα-3)Galβ-4Glcβ-1Cer, and GalNAc-GD1a. Our results revealed that unlike the compact and rigid oligosaccharide head group found in GM2, where the Neu5Ac and the GalNAc residues interact, the sugar chain of 6′-GM2 is in an open spatial arrangement, with the Neu5Ac no longer interacting with GalNAc, freely accessible to external interactions. The structure of GD1a can be regarded as that of GM2 with an extension of the terminal Neu5Acα-3Galβ-disaccharide. The inner portion of GD1a is that of GM2 comprising the very rigid GalNAc-[Neu5Ac-]Gal trisaccharide. The terminal Neu5Ac-Gal linkage is flexible and fluctuates between two limiting conformations. In GalNAc-GD1a the outer sialic acid gains conformational rigidity due to the presence of the outer GalNAc in position 4 of galactose. This ganglioside has two ‘core’ GalNAc-[Neu5Ac-]Gal trisaccharide linked in tandem.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1020269518303
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  • 4
    Electronic Resource
    Electronic Resource
    Synthesis of deoxygalactose-containing sialyl LeX ganglioside analogues to elucidate the structure necessary for selectin recognition (1996)
    Springer
    Glycoconjugate journal 13 (1996), S. 241-254 
    Details
    ISSN: 1573-4986
    Keywords: 6-deoxy-Gal ; 4-deoxy-Gal ; 4,6-dideoxy-Gal ; sialyl LeX ; sialoglycoconjugate ; selectin family
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Sialyl Lewis X ganglioside analogues containing 4-deoxy-, 6-deoxy-, and 4,6-dideoxy-d-galactopyranose in place ofd-galactopyranose have been synthesized. Glycosylations of 2-(trimethylsilyl)ethyl 2,6-di-O-benzyl-β-d-galactopyranoside and 2-(trimethylsilyl)ethyl β-d-fucopyranoside with the phenyl 2-thioglycoside derivative of sialic acid, usingN-iodosuccinimide (NIS)-trifluoromethanesulfonic acid (TfOH) as the promoter in acetonitrile, gave the desired 2-(trimethylsilyl)ethyl sialyl-α-(2→3)-β-d-galactopyranoside and-β-d-fucopyranoside, respectively. The sialylgalactose derivative obtained was then modified to 4-deoxy and 4,6-dideoxy derivatives. These were converted, byO-benzoylation, transformation of the 2-(trimethylsilyl)ethyl group to trichloroacetimidates, and introduction of the methylthio group with methylthiomethysilane, into the corresponding glycosyl donors, which were then coupled with 2-(trimethylsilyl)ethylO-(2,3,4-tri-O-benzyl-α-l-fucopyranosyl)-(1→3)-O-(2-acetamido-6-O-benzyl-2-deoxy-β-d-glucopyranosyl)-(1→3)-2,4,6- tri-O-benzyl-β-d-galactopyranoside in the presence of dimethyl(methylthio)sulfonium triflate (DMTST). The resulting pentasaccharides were each converted to the corresponding α-trichloroacetimidates, which, on coupling with (2S, 3R, 4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol, gave the desired sphingosine derivatives. Selective reduction of the azide group,N-acylation with octadecanoic acid,O-deacylation, and saponification of the methyl ester afforded the target compounds.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00731499
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  • 5
    Electronic Resource
    Electronic Resource
    Sialidase of swine influenza A viruses: variation of the recognition specificities for sialyl linkages and for the molecular species of sialic acid with the year of isolation (1995)
    Springer
    Glycoconjugate journal 12 (1995), S. 156-161 
    Details
    ISSN: 1573-4986
    Keywords: Influenza virus ; sialidase specificity ; gangliosides
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The sialidase of swine influenza A viruses of N1 and N2 subtypes, isolated from 1930 to 1992, was studied for substrate specificity with ganglio-series, lacto-series type II and GM3 gangliosides containing Neu5Acα2-3Gal, Neu5Gcα2-3Gal and Neu5Acα2-6Gal linkages. All viral sialidases tested showed that the activity for hydrolysing substrates with Neu5Acα2-3Gal was higher than the activities with Neu5Gcα2-3Gal and Neu5Acα2-6Gal linkages. When GM1b, GM3 and sialylparagloboside were used as substrates, the earliest strain (A/Wisconsin/15/30 H1N1, isolated in 1930) showed the activity ratio of Neu5Acα2-6Gal to Neu5Acα2-3Gal to be 0.13:0.2, and the ratio Neu5Gcα2-3Gal/Neu5Acα2-3Gal to be 0.19:0.37, while those strains isolated from 1978 to 1992 exhibited ratios of 0.29:0.58 for Neu5Acα2-6Gal/Neu5Acα2-3Gal and 0.51:0.76 for Neu5Gcα2-3Gal/Neu5Acα2-3Gal. The above results indicate that the substrate specificities of sialidases from swine influenza A viruses towards sialyl linkages and the molecular species of sialic acid are related to the year of isolation, i.e. strains isolated after 1978 exhibited higher activity towards Neu5Acα2-6Gal and Neu5Gcα2-3Gal linkages when compared with strains isolated in an earlier year, 1930.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00731360
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  • 6
    Electronic Resource
    Electronic Resource
    New ganglioside analogs that inhibit influenze virus sialidase (1990)
    Springer
    Glycoconjugate journal 7 (1990), S. 349-356 
    Details
    ISSN: 1573-4986
    Keywords: sialidase inhibitor ; Thioglycoside-analog of ganglioside ; influenza virus
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Synthetic thioglycoside-analogs of gangliosides such as Neu5Acα)2-S-6)Glcβ-(1-1)Ceramide (1) and the GM3 analog Neu5Acα(2-S-6)Galβ-(1–4)Glcβ(1-1)Ceramide (2), competitively inhibited GM3 hydrolysis by the sialidase of different subtypes of human and animal influenza viruses with an apparent Ki value of 2.8×10−6 and 1.5×10−5 M, respectively. The inhibitory activity of the ganglioside GM4 analog [Neu5Acα-(2-S-6)Galβ-(1-1)Ceramide (3)], in which the glucose of 1 was substituted by galactose, was lower than that of 1 (Ki =1.0×10−4 M). The thioglycoside-analogs (1, 2, 3) of the gangliosides were nonhydrolyzable substrates for influenza virus sialidase. The inhibitory activity of 1 to bacterial sialidases fromClostridium perfringens andArthrobacter ureafaciens was considerably lower than that to influenza virus sialidase, indicating that the structure of the active site in bacterial and influenza virus sialidase may be different and the analogs may be useful to determine the orientation of the substrate to the active site of sialidases, especially of influenza viruses.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01073378
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  • 7
    Electronic Resource
    Electronic Resource
    Synthesis of chemically modified sialic acid-containing sialyl-LeX ganglioside analogues recognized by the selectin family (1993)
    Springer
    Glycoconjugate journal 10 (1993), S. 3-15 
    Details
    ISSN: 1573-4986
    Keywords: sialic acid ; (2S)-sialyl-(2 → 3)-glycoside ; sialyl LeX ; sialoglycoconjugate ; selectin family
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Sialyl Lewis X ganglioside analogues containing 5-acetamido-3,5-dideoxy-l-arabino-2-heptulopyranosylonic acid (C7-Neu5Ac), 5-acetamido-3,5-dideoxy-d-galacto-2-octulopyranosylonic acid (C8-Neu5Ac), and 5-acetamido-3,5-dideoxy-l-glycero-d-galacto-1-2-nonulopyranosylonic acid (8-epi-Neu5Ac) in place ofN-acetylneuraminic acid (Neu5Ac) have been synthesized. Glycosylation of 2-(trimethylsilyl)ethyl 6-O-benzoyl-β-d-galactopyranoside with the phenyl or methyl 2-thioglycoside derivatives of the respective sialic acids, usingN-iodosuccinimide (NIS)-trifluoromethanesulfonic acid as a promoter in acetonitrile, gave the three required 2-(trimethylsilyl)ethyl (2S)-sialyl-(2 → 3)-β-galactopyranosides. These were converted viaO-benzoylation, selective transformation of the 2-(trimethylsilyl)ethyl group to acetyl, and introduction of the methylthio group with methylthiotrimethylsilane into the corresponding glycosyl donors. Glycosylation of 2-(trimethylsilyl)ethylO-(2,3,4-tri-O-benzyl-α-l-fucopyranosyl)-(1 → 3)-O-(2-acetamido-6-O-benzyl-2-deoxy-β-d-glucopyranosyl)-(1 → 3)-2,4,6-tri-O-benzyl-β-d-galactopyranoside with these donors in the presence of dimethyl(methylthio)sulfonium triflate (DMTST) afforded the expected β-glycosides, which were converted into the corresponding α-trichloroacetimidates, and these, on coupling with (2S, 3R, 4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol, gave the required β-glycosides. Finally, these were transformed via selective reduction of the azide group, condensation with octadecanoic acid,O-deacylation, and de-esterification into the target compounds in good yields.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00731181
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  • 8
    Electronic Resource
    Electronic Resource
    Total synthesis of a cholinergic neuron-specific ganglioside GT1aα: A high affinity ligand for myelin-associated glycoprotein (MAG) (1999)
    Springer
    Glycoconjugate journal 16 (1999), S. 585-598 
    Details
    ISSN: 1573-4986
    Keywords: ganglioside GT1aα ; sialic acid ; cholinergic neuron-specific antigen ; myelin-associated glycoprotein
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract An efficient total synthesis of a cholinergic neuron-specific ganglioside GT1aα (IV3NeuAcIII6NeuAcII3NeuAc-GgOse4Cer) is described. The suitably protected sialyl-α(2→6)-gangliotriose (III6NeuAc-GgOse3) derivative was glycosylated with the phenyl 2-thioglycoside of sialic acid in the presence of N-iodosuccinimide (NIS) and trimethylsilyl trifluoromethanesulfonate (TMSOTf) in acetonitrile medium, giving the disialogangliotriose (III6NeuAcII3NeuAc-GgOse3) derivative which contains both sialyl-α(2→6)-GalNAc and sialyl-α(2→3)-Gal structures (Route I). This pentasaccharide was efficiently synthesized also by the coupling of (methyl 5-acetamido-4,7,8,9-tetra-Ο-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2→6)-2-deoxy-3,4-Ο-isopropylidene-2-phthalimido-D-galactopyranosyl trichloroacetimidate with 2-(trimethylsilyl)ethyl (methyl 5-acetamido-4,7,8,9-tetra-Ο-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2→3)-(2,6-di-Ο-benzyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-Ο-benzyl-β-D-glucopyranoside, followed by conversion of the phthalimido group to the acetamido group (Route II). Ο-Deisopropylidenation and further glycosylation with methyl (methyl 5-acetamido-4,7,8,9-tetra-Ο-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2→3)-2,4,6-tri-Ο-benzoyl-1-thio-β-D-galactopyranoside, promoted by dimethyl(methylthio)sulfonium triflate (DMTST), gave the desired trisialogangliotetraose (IV3NeuAcIII6NeuAcII3NeuAc-GgOse4) derivative, which was converted stepwise into the title ganglioside GT1aα by the introduction of the ceramide part and then complete deprotection. The ganglioside obtained was shown to be identical with the native GT1aα on TLC-immunostaining.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1007020815583
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  • 9
    Electronic Resource
    Electronic Resource
    Detailed acceptor specificities of human α1,3-fucosyltransferases, Fuc-TVII and Fuc-TVI (1998)
    Springer
    Glycoconjugate journal 15 (1998), S. 969-974 
    Details
    ISSN: 1573-4986
    Keywords: Acceptor specificity ; α1,3-Fucosyltransferase ; Key functional group ; Selectin ; Sialyl Lewis x
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract To clarify the acceptor specificity of Fuc-TVII, its activity toward various analogs of a 2-(trimethylsilyl)ethyl α2,3-sialyl lacto-N-neotetraose, an acceptor for both Fuc-TVII and Fuc -TVI, was examined in comparison with that of Fuc-TVI. Fuc-TVII required three portions of α2,3-sialylated type-2 oligosaccharide structures (i.e., the hydroxyl group at C-4 of Gal, the hydroxyl group at C-3 of GlcNAc, and the carbonylamino group at C-2 of GlcNAc) for its acceptor recognition. Fuc-TVI required the carbonylamino group at C-2 of GlcNAc for its acceptor recognition. Fuc-TVI I showed higher affinity toward two analogs, in which the hydroxyl group at C-6 of GlcNAc has been deoxygenated and the acetamide group of N-acetylneuraminic acid has been replaced with a glycolylamino group, respectively, than that toward the original compound. On the other hand, Fuc-TVI showed higher affinity toward an analog, in which the acetamide group of GlcNAc has been modified with a lauroylamino group, than that toward the original compound. Analysis involving mass spectrometry confirmed that both Fuc-TVII and Fuc-TVI could fucosylate these three analogs to yield sialyl Lewis x derivatives.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1006933808303
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  • 10
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    Selective Expansion of the GM3 Glycolipid Monolayer Induced by Carbohydrate−Carbohydrate Interaction with Gg3 Trisaccharide-Bearing Glycoconjugate Polystyrene at the Air−Water Interface (2002)
    American Chemical Society
    Details
    Publication Date: 2002-09-01
    Print ISSN: 0743-7463
    Electronic ISSN: 1520-5827
    Topics: Chemistry and Pharmacology
    Published by American Chemical Society
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