A sphingolipid
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Ganglioside GM1 (bovine) (ammonium salt)

Item No. 31548

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-O-[O-β-D-galactopyranosyl-(1→3)-O-2-(acetylamino)-2-deoxy-β-D-galactopyranosyl-(1→4)-O-[N-acetyl-α-neuraminosyl-(2→3)]-O-β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyl]-ceramide, monoammonium salt
CAS Number
1007119-81-4
Synonyms
  • GM1
  • Monosialoganglioside GM1
Molecular Formula
C73H130N3O31 • NH4 (for stearoyl)
Formula Weight
1563.9
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol:DI Water (2:1:0.1): solubleWater: Forms micellar solution
SMILES
[H][C@](CO[C@@H]1O[C@@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O[C@@H]3O[C@@H]([C@@H]([C@@H]([C@H]3NC(C)=O)O[C@H]4[C@@H]([C@H]([C@H]([C@H](O4)CO)O)O)O)O)CO)O[C@@]5(C([O-])=O)O[C@]([C@@H]([C@@H](CO)O)O)([H])[C@H](NC(C)=O)[C@@H](O)C5)O)CO)([C@@H](/C=C/CCCCCCCCCCCCC)O)NC([R])=O.[NH4+]
InChi Code
InChI=1S/C73H131N3O31.H3N/c1-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-52(87)76-44(45(84)33-31-29-27-25-23-21-18-16-14-12-10-8-6-2)41-98-69-61(94)59(92)63(50(39-80)101-69)103-71-62(95)67(107-73(72(96)97)35-46(85)53(74-42(3)82)66(106-73)55(88)47(86)36-77)64(51(40-81)102-71)104-68-54(75-43(4)83)65(57(90)49(38-79)99-68)105-70-60(93)58(91)56(89)48(37-78)100-70;/h31,33,44-51,53-71,77-81,84-86,88-95H,5-30,32,34-41H2,1-4H3,(H,74,82)(H,75,83)(H,76,87)(H,96,97);1H3/b33-31+;/t44-,45+,46-,47+,48+,49+,50+,51+,53+,54+,55+,56-,57-,58-,59+,60+,61+,62+,63+,64-,65+,66+,67+,68-,69+,70-,71-,73-;/m0./s1
InChi Key
XKTKEUMFELHBSG-POYTVKKJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Ganglioside GM1 is a monosialylated ganglioside and the prototypic ganglioside for those containing one sialic acid residue.1,2 It is found in a large variety of cells, including immune cells and neurons, and is enriched in lipid rafts in the cell membrane.3 It associates with growth factor receptors, including TrkA, TrkB, and the GDNF receptor complex containing Ret and GFRα, and is required for TrkA expression on the cell surface. Ganglioside GM1 interacts with other proteins to increase calcium influx, affecting various calcium-dependent processes, including inducing neuronal outgrowth during differentiation. Ganglioside GM1 acts as a receptor for cholera toxin, which binds to its oligosaccharide group, facilitating toxin cell entry into epithelial cells of the jejunum.4,5 Similarly, it is bound by the heat-labile enterotoxin from E. coli in the pathogenesis of traveler's diarrhea.6 Ganglioside GM1 sensitizes inactivated T cells to TNF-α-induced apoptosis and induces apoptosis of activated T cells even in the absence of TNF-α.7 Ganglioside GM1 is found at higher levels on T cells isolated from patients with renal cell carcinoma (RCC) compared with T cells from patients without cancer. Levels of ganglioside GM1 are decreased in the substantia nigra pars compacta in postmortem brain from patients with Parkinson's disease.3 Ganglioside GM1 gangliosidosis, characterized by a deficiency in GM1-β-galactosidase, the enzyme that degrades ganglioside GM1, leads to accumulation of the gangliosides GM1 and GA1 in neurons and can be fatal in infants.1 This product contains ganglioside GM1 molecular species with primarily C18:0 fatty acyl chain lengths. As this product is derived from a natural source, there may be variations in the sphingoid backbone. [Matreya, LLC. Catalog No. 1061]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kolter, T. Ganglioside biochemistry. ISRN Biochem. 506160 (2012).

    2. Mocchetti, I. Exogenous gangliosides, neuronal plasticity and repair, and the neurotrophins. Cell Mol. Life Sci. 62(19-20), 2283-2294 (2005).

    3. Ledeen, R.W., and Wu, G. The multi-tasked life of GM1 ganglioside, a true factotum of nature. Trends Biochem. Sci. 40(7), 407-418 (2015).

    4. Turnbull, W.B., Precious, B.L., and Homans, S.W. Dissecting the cholera toxin-ganglioside GM1 interaction by isothermal titration calorimetry. J. Am. Chem. Soc. 126(4), 1047-1054 (2004).

    5. Blank, N., Schiller, M., Krienke, S., et al. Cholera toxin binds to lipid rafts but has a limited specificity for ganglioside GM1. Immunol. Cell Biol. 85(5), 378-382 (2007).

    6. Minke, W.E., Roach, C., Hol, W.G., et al. Structure-based exploration of the ganglioside GM1 binding sites of Escherichia coli heat-labile enterotoxin and cholera toxin for the discovery of receptor antagonists. Biochemistry 38(18), 5684-5692 (1999).

    7. Das, T., Sa, G., Hilston, C., et al. GM1 and tumor necrosis factor-ɑ, overexpressed in renal cell carcinoma, synergize to induce T-cell apoptosis. Cancer Res. 68(6), 2014-2023 (2008).