A sphingolipid
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Ganglioside GD1a (porcine) (ammonium salt)

Item No. 31707

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
CAS Number
12707-58-3
Synonyms
  • Ganglioside B1
  • Ganglioside G3
Molecular Formula
C84H146N4O39 • 2NH4 (for stearoyl)
Formula Weight
1872.2
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol:Water (2:1:0.1): Soluble
SMILES
OC[C@H]1O[C@@H](O[C@H]2[C@H](O[C@H]([C@@H]([C@H]2O[C@]3(C([O-])=O)C[C@@H]([C@H]([C@]([C@@H]([C@@H](CO)O)O)(O3)[H])NC(C)=O)O)O)O[C@H]4[C@@H]([C@H]([C@@H](O[C@@H]4CO)OC[C@@H]([C@H](O)/C=C/CCCCCCCCCCCCC)NC([R])=O)O)O)CO)[C@H](NC(C)=O)[C@@H](O[C@@H]5O[C@@H]([C@@H]([C@@H]([C@H]5O)O[C@]6(C([O-])=O)C[C@@H]([C@H]([C@]([C@@H]([C@@H](CO)O)O)(O6)[H])NC(C)=O)O)O)CO)[C@H]1O.[NH4+].[NH4+]
InChi Code
InChI=1S/C84H148N4O39.2H3N/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-58(103)88-48(49(98)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2)44-116-78-67(109)66(108)70(56(42-93)119-78)121-80-69(111)76(127-84(82(114)115)37-51(100)60(86-46(4)96)74(125-84)63(105)53(102)39-90)71(57(43-94)120-80)122-77-61(87-47(5)97)72(64(106)54(40-91)117-77)123-79-68(110)75(65(107)55(41-92)118-79)126-83(81(112)113)36-50(99)59(85-45(3)95)73(124-83)62(104)52(101)38-89;;/h32,34,48-57,59-80,89-94,98-102,104-111H,6-31,33,35-44H2,1-5H3,(H,85,95)(H,86,96)(H,87,97)(H,88,103)(H,112,113)(H,114,115);2*1H3/b34-32+;;/t48-,49+,50-,51-,52+,53+,54+,55+,56+,57+,59+,60+,61+,62+,63+,64-,65-,66+,67+,68+,69+,70+,71-,72+,73+,74+,75-,76+,77-,78+,79-,80-,83-,84-;;/m0../s1
InChi Key
OSJQKBXRNIDBRB-ZKSQSZPPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Ganglioside GD1a is a sialic acid-containing glycosphingolipid found in brain, erythrocytes, bone marrow, testis, spleen, and liver.1 It can be shed from the surface of tumor cells into the microenvironment where it influences tumor-host cell interactions to promote tumor cell proliferation, invasion, and metastasis. Ganglioside GD1a (20 μM) also increases endothelial cell proliferation. Furthermore, ganglioside GD1a has been shown to act as a functional coreceptor for toll-like receptor 2 (TLR2), enabling the recruitment of TLR2 to lipid rafts when bound by a bacterial toxin.2 This product contains ganglioside GD1a 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. 1546]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Mukherjee, P., Faber, A.C., Shelton, L.M., et al. Thematic review series: Sphingolipids. Ganglioside GM3 suppresses the proangiogenic effects of vascular endothelial growth factor and ganglioside GD1a. J. Lipid Res. 49(5), 929-938 (2008).

    2. Liang, S., Wang, M., Tapping, R.I., et al. Ganglioside GD1a is an essential coreceptor for Toll-like receptor 2 signaling in response to the B subunit of type IIb enterotoxin. The Journal of Biological Chemisty 282(10), 7532-7542 (2007).