An internal standard for the quantification of ganglioside GD3
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C18 Ganglioside GD3-d3 (ammonium salt)

Item No. 24852

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(1S,2R,3E)-1-[[[O-(N-acetyl-α-neuraminosyl)-(2→8)-O-(N-acetyl-α-neuraminosyl)-(2→3)-O-β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyl]oxy]methyl]-2-hydroxy-3-heptadecen-1-yl]-octadecanamide-18,18,18-d3, diammonium salt
CAS Number
2692624-24-9
Synonyms
  • Disialosyllactosylceramide-d3
  • N-omega-CD3-Octadecanoyl Disialoganglioside GD3 -d3
Molecular Formula
C70H120D3N3O29 • 2NH4
Formula Weight
1509.8
Purity
≥99% deuterated forms (d1 -d3)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol:Water (2:1:0.1): Soluble
SMILES
OC[C@H]1O[C@@H](OC[C@H](NC(CCCCCCCCCCCCCCCCC([2H])([2H])[2H])=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@H](O[C@@]3(C([O-])=O)O[C@@H]([C@H](O)[C@H](O[C@@]4(C([O-])=O)O[C@@H]([C@H](O)[C@@H](CO)O)[C@H](NC(C)=O)[C@@H](O)C4)CO)[C@H](NC(C)=O)[C@@H](O)C3)[C@H]2O.[NH4+].[NH4+]
InChi Code
InChI=1S/C70H125N3O29.2H3N/c1-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-52(84)73-44(45(80)33-31-29-27-25-23-21-18-16-14-12-10-8-6-2)41-95-65-59(89)58(88)61(51(40-77)97-65)98-66-60(90)64(56(86)49(38-75)96-66)102-70(68(93)94)36-47(82)54(72-43(4)79)63(101-70)57(87)50(39-76)99-69(67(91)92)35-46(81)53(71-42(3)78)62(100-69)55(85)48(83)37-74;;/h31,33,44-51,53-66,74-77,80-83,85-90H,5-30,32,34-41H2,1-4H3,(H,71,78)(H,72,79)(H,73,84)(H,91,92)(H,93,94);2*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-,69+,70-;;/m0../s1/i1D3;;
InChi Key
VFVCOMSDNRUTEK-MRGKXOJUSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    C18 Ganglioside GD3-d3 is intended for use as an internal standard in the quantification of ganglioside GD3 (Item No. 17481) by GC- or LC-MS. Ganglioside GD3 is synthesized by the addition of two sialic acid residues to lactosylceramide (Item No. 16983) and can serve as a precursor to the formation of more complex gangliosides by the action of glycosyl- and sialyltransferases. With roles in cell proliferation and differentiation, its expression increases during development and in pathological conditions such as cancer.1 Furthermore, the intracellular accumulation of ganglioside GD3 can contribute to mitochondrial damage, a crucial event during apoptosis.2 Ganglioside GD3 has become a target for therapeutic approaches to prevent malignant properties of tumor cells like melanoma.1,3 As this product is derived from a natural source, there may also be variations in the sphingoid backbone. [Matreya, LLC. Catalog No. 2054]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hamamura, K., Furukawa, K., Hayashi, T., et al. Ganglioside GD3 promotes cell growth and invasion through p130Cas and paxillin in malignant melanoma cells. Proc. Natl. Acad. Sci. USA 102(31), 11041-11046 (2005).

    2. De Maria, R., Lenti, L., Malisan, F., et al. Requirement for GD3 ganglioside in CD95- and ceramide-induced apoptosis. Science 277(5332), 1652-1655 (1997).

    3. Nicoll, G., Avril, T., Lock, K., et al. Ganglioside GD3 expression on target cells can modulate NK cell cytotoxicity via siglec-7-dependent and -independent mechanisms. Eur. J. Immunol. 33(6), 1642-1648 (2003).