A sphingolipid
Technical Support & Resources

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Ganglioside GD1a (bovine) (ammonium salt)

Item No. 31591

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
CAS Number
12707-58-3
Synonyms
  • Disialoganglioside GD1a
Molecular Formula
C84H146N4O39 • 2NH4 (for stearoyl)
Formula Weight
1872.2
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol:DI 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
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    5 mg

    $316

    Add
    Lipid Resource Center
    Discover Products & Resources for Lipid Research
    • High-purity lipid standards
    • Lipid roles in biology
    • Lipids in health & disease
    • Lipids for pharmaceutical development
    • Protocols, advice, & resources
    EXPLORE NOW
    Product Description

    Ganglioside GD1a is a sialic acid-containing glycosphingolipid that has been found in brain, erythrocytes, bone marrow, testis, spleen, and liver, as well as in serum lipoproteins.1,2 It is shed into the tumor microenvironment from the surface of tumor cells, where it influences tumor-host cell interactions to promote tumor cell proliferation, invasion, and metastasis.3 It functions as a toll-like receptor 2 (TLR2) co-receptor in isolated human monocytes, colocalizing with TLR2 and enhancing the binding of type IIb E. coli enterotoxin (LT-IIb-B5) to TLR2 when used at a concentration of 20 µM.4 Ganglioside GD1a (20 µM) increases VEGF-induced proliferation of human umbilical vein endothelial cells (HUVECs), as well as induces vascularization in a Matrigel™ plug assay in mice when used at a concentration of 20 µM/plug.3 It accumulates in the CNS of patients with galactosialidosis, a lysosomal storage disorder.5 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. 1062]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Iwamori, M., Shimomura, J., Tsuyuhara, S., et al. Gangliosides of various rat tissues: Distribution of ganglio-N-tetraose-containing gangliosides and tissue-characteristic composition of gangliosides. J. Biochem. 95(3), 761-770 (1984).

    2. Senn, H.J., Orth, M., Fitzke, E., et al. Gangliosides in normal human serum. Concentration, pattern and transport by lipoproteins. Eur. J. Biochem. 181(3), 657-662 (1989).

    3. 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).

    4. 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).

    5. Walkley, S.U. Secondary accumulation of gangliosides in lysosomal storage disorders. Semin. Cell Dev. Biol. 15(4), 433-444 (2004).