An internal standard for the quantification of C18 ganglioside GM2
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C18 Ganglioside GM2-d7 (d18:1/18:0-d7) (ammonium salt, synthetic)

Item No. 39641

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(1S,2R,3E)-1-[[[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]oxy]methyl]-2-hydroxy-3-heptadecen-1-yl]-octadecanamide-16,16,17,17,18,18,18-d7, monoammonium salt
Synonyms
  • C18 GM2-d7
  • Monosialoganglioside GM2-d7
  • N-omega-CD7-Octadecanoyl monosialoganglioside GM2
  • N-Stearoyl Monosialoganglioside GM2-d7
Molecular Formula
C67H113D7N3O26 • NH4
Formula Weight
1408.8
Purity
≥99% deuterated forms (d1-d7)
Formulation
A solution in methanol
Solubility(Learn about Variance in Solubility)
Methanol: Soluble
SMILES
OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@@]2([H])[C@@H]([C@@]([C@H]([C@H](O2)CO)O[C@]3([H])O[C@@H]([C@@H]([C@@H]([C@H]3NC(C)=O)O)O)CO)([H])O[C@]4(C([O-])=O)C[C@H](O)[C@@H](NC(C)=O)[C@H]([C@@H]([C@H](O)CO)O)O4)O)O[C@H]1OC[C@@H]([C@H](O)/C=C/CCCCCCCCCCCCC)NC(CCCCCCCCCCCCCCC([2H])([2H])C([2H])([2H])C([2H])([2H])[2H])=O.[NH4+]
InChi Code
InChI=1S/C67H121N3O26.H3N/c1-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-50(80)70-43(44(77)33-31-29-27-25-23-21-18-16-14-12-10-8-6-2)40-89-64-57(85)56(84)59(48(38-73)91-64)93-65-58(86)62(60(49(39-74)92-65)94-63-52(69-42(4)76)55(83)54(82)47(37-72)90-63)96-67(66(87)88)35-45(78)51(68-41(3)75)61(95-67)53(81)46(79)36-71;/h31,33,43-49,51-65,71-74,77-79,81-86H,5-30,32,34-40H2,1-4H3,(H,68,75)(H,69,76)(H,70,80)(H,87,88);1H3/b33-31+;/t43-,44+,45-,46+,47+,48+,49+,51+,52+,53+,54-,55+,56+,57+,58+,59+,60-,61+,62+,63-,64+,65-,67-;/m0./s1/i1D3,5D2,7D2;
InChi Key
OUYSNHGGXMUSJO-WHQUDGAJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    C18 Ganglioside GM2-d7 (d18:1/18:0-d7) is intended for use as an internal standard for the quantification of C18 ganglioside GM2 by GC- or LC-MS. C18 Ganglioside GM2 is a monosialylated ganglioside found in the mammalian brain where it is localized to the cell membrane.1 It accumulates in Tay-Sachs and Sandhoff disease, which are neurodegenerative disorders characterized by deficiency of lysosomal β-hexosaminidase A and B, respectively.2 Ganglioside GM2 disrupts the function of immune cells and, when used at a concentration of 25 µM, increases migration and invasion of SK-RC-45 cells with no effect on proliferation.3 This product is fully synthetic and has no variations in the fatty acyl chain or sphingoid backbone. It is intended for use as an analytical standard for the quantification of C18 ganglioside GM2 by GC-MS.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Schnaar, R.L. Gangliosides of the vertebrate nervous system. J. Mol. Biol. 428(16), 3325-3336 (2016).

    2. Baek, R.C., Martin, D.R., Cox, N.R., et al. Comparative analysis of brain lipids in mice, cats, and humans with Sandhoff disease. Lipids 44(3), 197-205 (2009).

    3. Kundu, M., Mahata, B., Banerjee, A., et al. Ganglioside GM2 mediates migration of tumor cells by interacting with integrin and modulating the downstream signaling pathway. Biochim. Biophys. Acta 1863(7 Pt A), 1472-1489 (2016).