An internal standard for the quantification of C18 ganglioside GM1
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Unlabeled Version(s)
42980C18 Ganglioside GM1 (d18:1/18:0) (ammonium salt)
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C18 Ganglioside GM1-d3 (d18:1/18:0-d3) (ammonium salt)

Item No. 24839

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S,4S,5R,6R)-5-acetamido-2-(((2R,3S,4R,5R,6S)-3-(((2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-(((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-6-(((2R,3S,4R,5R,6R)-4,5-dihydroxy-6-(((2S,3R,E)-3-hydroxy-2-(octadecanamido-18,18,18-d3)octadec-4-en-1-yl)oxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-5-hydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylate
Synonyms
  • N-omega-CD3-Octadecanoyl monosialoganglioside GM1-d3
  • N-CD3-Stearoyl-GM
  • C18 GM1-d3
  • GM1 (18:1/18:0-d3)
  • GM1 (d18:1/C18:0)-d3
  • Monosialoganglioside GM1-d3
  • N-Stearoyl Monosialoganglioside GM1-d3
Molecular Formula
C73H127D3N3O31 • NH4
Formula Weight
1566.9
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]([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[C@@]4([H])[C@@H]([C@H]([C@H]([C@H](O4)CO)O)O)O)O)CO)([H])O[C@]5(C([O-])=O)C[C@H](O)[C@@H](NC(C)=O)[C@H]([C@@H]([C@H](O)CO)O)O5)O)O[C@H]1OC[C@@H]([C@H](O)/C=C/CCCCCCCCCCCCC)NC(CCCCCCCCCCCCCCCCC([2H])([2H])[2H])=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/i1D3;
InChi Key
XKTKEUMFELHBSG-IAQALZRHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $736

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    Product Description

    C18 Ganglioside GM1-d3 (d18:1/18:0-d3) is intended for use as an internal standard for the quantification of C18 ganglioside GM1. Ganglioside GM1 is a monosialylated ganglioside and the prototypic ganglioside for those containing one sialic acid residue.1,2 C18 Ganglioside GM1 is found in the brain, primarily in the piriform cortex, amygdala nucleus, striatum, and hippocampal CA1 region.3 The ratio of C18 ganglioside GM1 (d20:1/18:0) to C18 ganglioside GM1 is decreased in the outer molecular layer of the hippocampal dentate gyrus in postmortem tissue from patients with Alzheimer’s disease.4 As this product is derived from a natural source, there may be variations in the sphingoid backbone. [Matreya, LLC. Catalog No. 2050]

    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. Andres, A.D., Young, L.E.A., Gentry, M.S., et al. Spatial profiling of gangliosides in mouse brain by mass spectrometry imaging. J. Lipid Res. 61(12), 1537 (2020).

    4. Hirano-Sakamaki, W., Sugiyama, E., Hayasaka, T., et al. Alzheimer’s disease is associated with disordered localization of ganglioside GM1 molecular species in the human dentate gyrus. FEBS Lett. 589(23), 3611-3616 (2015).