A sphingolipid
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Globotetraosylceramide (porcine RBC)

Item No. 24881

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-O-[O-2-(acetylamino)-2-deoxy-β-D-galactopyranosyl-(1→3)-O-α-D-galactopyranosyl-(1→4)-O-β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyl]-ceramide
CAS Number
11034-93-8
Synonyms
  • Gb4Cers (porcine RBC)
  • Globoside (porcine RBC)
  • Globotetrahexosylceramide (porcine RBC)
Molecular Formula
C68H126N2O23 (for tetracosanoyl)
Formula Weight
1339.7
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol (2:1): SolubleDMSO: SolubleMethanol: Warmed
SMILES
OC[C@H]1O[C@@H](OC[C@H](NC([R])=O)[C@H](O)/C=C/CCCCCCCCCCCCC)[C@H](O)[C@@H](O)[C@@H]1O[C@]2([H])O[C@H](CO)[C@H](O[C@@]3([H])O[C@H](CO)[C@H](O)[C@H](O[C@]4([H])O[C@H](CO)[C@H](O)[C@H](O)[C@H]4NC(C)=O)[C@H]3O)[C@H](O)[C@H]2O
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $636

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    Product Description

    Globotetraosylceramides are bioactive neutral glycosphingolipids. They are the major glycolipids in human erythrocytes.1 They act as receptors for the Shiga toxins Stx1, Stx2, and Stx2e, the cytotoxic protein pierisin-1, and parvovirus B19.2,3,4 Globotetraosylceramides increase the expression of proteins responsible for enamel deposition, including ameloblastin, amelogenin, and enamelin, in dental epithelial cells and activate the ERK and p38 MAPK signaling pathways.5 Levels of globotetraosylceramides are elevated in fibroblasts from patients with salt and pepper syndrome, a neurocutaneous condition characterized by intellectual disability and hyper- and hypo-pigmented skin.6 This product contains globotetraosylceramides with primarily C24:0, C22:0, and 2-hydroxy C24:0 fatty acyl chains. As this product is derived from a natural source, there may be variations in the sphingoid backbone. [Matreya, LLC. Catalog No. 1068]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yamakawa, T., Yokoyama, S., and Kiso, N. Structure of main globoside of human erythrocytes. J. Biochem. 52(3), 228-229 (1962).

    2. Müthing, J., Scheweppe, C.H., Karch, H., et al. Shiga toxins, glycosphingolipid diversity, and endothelial cell injury. Thromb. Haemost. 101(2), 252-264 (2009).

    3. Matsushima-Hibiya, Y., Watanabe, M., Hidari, J.I.-P.J., et al. Identification of glycosphingolipid receptors for pierisin-1, a guanine-specific ADP-ribosylating toxin from the cabbage butterfly. The Journal of Biological Chemisty 278(11), 9972-9978 (2003).

    4. Nasir, W., Nilsson, J., Ologsson, S., et al. Parvovirus B19 VLP recognizes globoside in supported lipid bilayers. Virology 456-457, 364-369 (2014).

    5. Nakamura, T., Chiba, Y., Naruse, M., et al. Globoside accelerates the differentiation of dental epithelial cells into ameloblasts. Int. J. Oral Sci. 8(4), 205-212 (2016).

    6. Boccuto, L., Aoki, K., Flanagan-Steet, H., et al. A mutation in a ganglioside biosynthetic enzyme, ST3GAL5, results in salt & pepper syndrome, a neurocutaneous disorder with altered glycolipid and glycoprotein glycosylation. Hum. Mol. Genet. 23(2), 418-433 (2014).