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Chemical Compound Review

AC1L5A3X     N-[(2S,3R,4R,5R,6R)-2- [(2R,3R,4R,5R,6R)-4...

Synonyms: 75645-24-8, Gangliotetraose, Gg4 Asialo-oligosaccharide
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Disease relevance of Gangliotetraose

  • Neuronal gangliosides (gangliotetraose series) were found in varying amounts in all medulloblastomas [1].
  • Although cells are usually resistant to homologous complement, the IgM antibody against gangliotetraose (Gg4), an asialo-oligosaccharide of GM1, was found to cause cytolysis of HIV-1 infected cells by homologous complement [2].
  • Differences in ganglioside patterns were observed, with neuroblastomas from patients who were either disease positive or dead of disease tending to have more monosialogangliosides and fewer gangliotetraose gangliosides of the B series (formula; see text) than tumors from patients who were disease-free [3].
  • Low levels of CSF gangliotetraose-series gangliosides in West syndrome: implication of brain maturation disturbance [4].

High impact information on Gangliotetraose

  • Mice engineered to lack GM2/GD2 synthase (GalNAc-T), with resultant deficit of GM2, GD2, and all gangliotetraose gangliosides, were originally described as showing a relatively normal phenotype with only a slight reduction in nerve conduction [5].
  • Some normal human sera contain a natural IgM antibody against gangliotetraose and GM2 which is capable of initiating complement-mediated cytolysis of HIV-1-infected cells [6].
  • Cultured neurons from mice genetically engineered to lack gangliotetraose gangliosides such as GM1 were highly vulnerable to Ca2+-induced apoptosis [7].
  • The nuclear envelope (NE), consisting of two unique membranes, is one such structure shown to contain members of the gangliotetraose family and possibly other sialoglycolipids [7].
  • The gangliosides of the gangliotetraose series were individually determined with cholera toxin subunit B by TLC-enzyme-linked immunosorbent assay (ELISA) after chromatography and subsequent sialidase hydrolysis to II3NeuAc-GgOse4Cer (GM1) [8].

Chemical compound and disease context of Gangliotetraose


Biological context of Gangliotetraose

  • Our previous study showed an impaired regulation of Ca(2+) homeostasis in cultured cerebellar granule neurons (CGN) from neonatal mice lacking GM2, GD2 and all gangliotetraose gangliosides, due to disruption of the GM2/GD2 synthase (GalNAc-T) gene [10].

Anatomical context of Gangliotetraose

  • All evidence thus points to cultured astrocytes of rat and chick brain containing appreciable gangliosides, most of which are GM3 and GD3 with the majority of the remainder comprising structures other than the gangliotetraose type [11].
  • The contents of GA1, GM3, GD3, GM2 and gangliotetraose-series gangliosides in ATL cells were all different, even though all the cells used have a common antigen reactive with monoclonal OKT-4 antibody, indicating that there are several subsets of human inducer/helper T-cells, which possess different metabolism and expression of gangliosides [12].
  • Gangliotetraose-series gangliosides, GM1a, GD1a and GD1b, were also found in cultured ATL cells, but were not detected in normal human lymphocytes or the lymphocytes of a patient with ATL [12].
  • The pronounced increases in gangliosides belonging to the gangliotetraose family during the neurite outgrowth phase of neuronal differentiation have suggested a functional requirement for these substances related to process extension, arborization, and possibly synaptogenesis [13].
  • The gangliotetraose ganglioside-deficient mutant cell line, NG-CR72, had significantly higher basal levels of GM2 in the plasma membrane compared to wild type NG108-15 cells, and this level increased significantly on treatment with dendritogenic agents [14].

Associations of Gangliotetraose with other chemical compounds


Gene context of Gangliotetraose

  • Knock-out (KO) mice lacking gangliotetraose gangliosides attributable to disruption of the gene for GM2/GD2 synthase [GalNAcT (UDP-N-acetylgalactosamine:GM3/GD3 beta-1,4-N-acetylgalactosaminyltransferase; EC [EC])] are revealing key neural functions for the complex gangliosides of brain [17].
  • Gangliosides of the gangliotetraose series were individually determined with cholera toxin B-subunit (CT-B) and an anti CT-B monoclonal antibody after chromatography and sialidase hydrolysis to GM1 on high performance thin-layer plates [16].

Analytical, diagnostic and therapeutic context of Gangliotetraose

  • Several underivatized mono- and bis-sulfated glycosphingolipids having gangliotriaose or gangliotetraose core structure were analyzed by negative liquid secondary ion mass spectrometry (LSIMS) with high- and low-energy collision-induced dissociation (CID) [18].
  • These changes, i.e. several-fold increase in concentration and appearance of the gangliotetraose family, have been observed both in vivo and in neuronal cell cultures [19].


  1. Determination of gangliosides in six human primary medulloblastomas. Gottfries, J., Fredman, P., Månsson, J.E., Collins, V.P., von Holst, H., Armstrong, D.D., Percy, A.K., Wikstrand, C.J., Bigner, D.D., Svennerholm, L. J. Neurochem. (1990) [Pubmed]
  2. IgM natural antibody against an asialo-oligosaccharide, gangliotetraose (Gg4), sensitizes HIV-I infected cells for cytolysis by homologous complement. Wu, X., Okada, N., Iwamori, M., Okada, H. Int. Immunol. (1996) [Pubmed]
  3. Ganglioside composition of human neuroblastomas. Correlation with prognosis. A Pediatric Oncology Group Study. Schengrund, C.L., Repman, M.A., Shochat, S.J. Cancer (1985) [Pubmed]
  4. Low levels of CSF gangliotetraose-series gangliosides in West syndrome: implication of brain maturation disturbance. Izumi, T., Ogawa, T., Koizumi, H., Fukuyama, Y. Pediatric neurology. (1993) [Pubmed]
  5. Cerebellar neurons lacking complex gangliosides degenerate in the presence of depolarizing levels of potassium. Wu, G., Xie, X., Lu, Z.H., Ledeen, R.W. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  6. Complement-mediated cytolysis and azidothymidine are synergistic in HIV-1 suppression. Okada, H., Wu, X., Okada, N. Int. Immunol. (1998) [Pubmed]
  7. Gangliosides of the nuclear membrane: a crucial locus of cytoprotective modulation. Ledeen, R.W., Wu, G. J. Cell. Biochem. (2006) [Pubmed]
  8. Gangliosides and sulphatide in human cerebrospinal fluid: quantitation with immunoaffinity techniques. Davidsson, P., Fredman, P., Svennerholm, L. J. Chromatogr. (1989) [Pubmed]
  9. Correlation of gangliotetraose gangliosides with neurite forming potential of neuroblastoma cells. Wu, G.S., Lu, Z.H., Ledeen, R.W. Brain Res. Dev. Brain Res. (1991) [Pubmed]
  10. Susceptibility of cerebellar granule neurons from GM2/GD2 synthase-null mice to apoptosis induced by glutamate excitotoxicity and elevated KCl: rescue by GM1 and LIGA20. Wu, G., Lu, Z.H., Xie, X., Ledeen, R.W. Glycoconj. J. (2004) [Pubmed]
  11. Gangliosides of cultured astroglia. Sbaschnig-Agler, M., Dreyfus, H., Norton, W.T., Sensenbrenner, M., Farooq, M., Byrne, M.C., Ledeen, R.W. Brain Res. (1988) [Pubmed]
  12. Aberrant expression of ganglioside and asialoglycosphingolipid antigens in adult T-cell leukemia cells. Suzuki, Y., Hirabayashi, Y., Matsumoto, N., Kato, H., Hidari, K., Tsuchiya, K., Matsumoto, M., Hoshino, H., Tozawa, H., Miwa, M. Jpn. J. Cancer Res. (1987) [Pubmed]
  13. The role of GM1 and other gangliosides in neuronal differentiation. Overview and new finding. Ledeen, R.W., Wu, G., Lu, Z.H., Kozireski-Chuback, D., Fang, Y. Ann. N. Y. Acad. Sci. (1998) [Pubmed]
  14. Comparison of ganglioside profiles in nuclei and whole cells of NG108-15 and NG-CR72 lines: changes in response to different neuritogenic stimuli. Wu, G., Lu, Z.H., Xie, X., Ledeen, R. Brain Res. Dev. Brain Res. (2001) [Pubmed]
  15. A trisialoganglioside containing a sialyl alpha 2-6 N-acetylgalactosamine residue is a cholinergic-specific antigen, Chol-1 alpha. Ando, S., Hirabayashi, Y., Kon, K., Inagaki, F., Tate, S., Whittaker, V.P. J. Biochem. (1992) [Pubmed]
  16. Determination of gangliosides and sulfatide in human cerebrospinal fluid with a microimmunoaffinity technique. Davidsson, P., Fredman, P., Månsson, J.E., Svennerholm, L. Clin. Chim. Acta (1991) [Pubmed]
  17. Enhanced susceptibility to kainate-induced seizures, neuronal apoptosis, and death in mice lacking gangliotetraose gangliosides: protection with LIGA 20, a membrane-permeant analog of GM1. Wu, G., Lu, Z.H., Wang, J., Wang, Y., Xie, X., Meyenhofer, M.F., Ledeen, R.W. J. Neurosci. (2005) [Pubmed]
  18. Structural analysis of mono- and bis-sulfated glycosphingolipids by negative liquid secondary ion mass spectrometry with high- and low-energy collision-induced dissociation. Tadano-Aritomi, K., Kubo, H., Ireland, P., Okuda, M., Kasama, T., Handa, S., Ishizuka, I. Carbohydr. Res. (1995) [Pubmed]
  19. Gangliosides as neurotrophic agents: studies on the mechanism of action. Ledeen, R.W., Wu, G., Cannella, M.S., Oderfeld-Nowak, B., Cuello, A.C. Acta neurobiologiae experimentalis. (1990) [Pubmed]
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