A sphingolipid
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Lyso-Monosialoganglioside GM1 (ammonium salt)

Item No. 24837

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S,3R,4E)-2-amino-3-hydroxy-4-octadecenyl O-(N-acetyl-α-neuraminosyl)-(2→3)-O-[O-β-D-galactopyranosyl-(1→3)-2-(acetylamino)-2-deoxy-β-D-galactopyranosyl-(1→4)]-O-β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside, monoammonium salt
Synonyms
  • Lysoganglioside GM1
  • Lyso-GM1
  • lyso-Monosialoganglioside GM1
Molecular Formula
C55H96N3O30 • NH4
Formula Weight
1297.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol:Water (2:1:0.1): Soluble
SMILES
N[C@H]([C@H](O)/C=C/CCCCCCCCCCCCC)CO[C@@H]1O[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)CO.[NH4+]
InChi Code
InChI=1S/C55H97N3O30.H3N/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-28(66)27(56)24-79-51-43(75)41(73)45(33(22-62)82-51)84-53-44(76)49(88-55(54(77)78)18-29(67)35(57-25(2)64)48(87-55)37(69)30(68)19-59)46(34(23-63)83-53)85-50-36(58-26(3)65)47(39(71)32(21-61)80-50)86-52-42(74)40(72)38(70)31(20-60)81-52;/h16-17,27-53,59-63,66-76H,4-15,18-24,56H2,1-3H3,(H,57,64)(H,58,65)(H,77,78);1H3/b17-16+;/t27-,28+,29-,30+,31+,32+,33+,34+,35+,36+,37+,38-,39-,40-,41+,42+,43+,44+,45+,46-,47+,48+,49+,50-,51+,52-,53-,55-;/m0./s1
InChi Key
YQTZTHWHSZKVRN-UVMZBQDWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $523

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    Product Description

    Lyso-monosialoganglioside GM1 (Lyso-GM1) is a form of ganglioside GM1 (Item No. 19579) that is lacking the fatty acyl group. Lyso-GM1 (2.5 µM) inhibits laminin-1-induced clustering of ganglioside GM1 in dorsal root ganglion (DRG) cells and also disrupts β1 integrin clustering and neurite outgrowth.1 It does not protect against glutamate-induced neurotoxicity in primary neuronal cultures.2 Elevated levels of lyso-GM1 have been found in the brain and spinal cord of patients with infantile- and late-infantile-type GM1-gangliosidosis, a neurodegenerative disorder characterized by deficiency of the enzyme β-galactosidase and accumulation of gangliosides.3 As this product is derived from a natural source, there may be variations in the sphingoid backbone. [Matreya, LLC. Catalog No. 1518]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ichikawa, N., Iwabuchi, K., Kurihara, H., et al. Binding of laminin-1 to monosialoganglioside GM1 in lipid rafts is crucial for neurite outgrowth. J. Cell Sci. 122(Pt 2), 289-299 (2009).

    2. Manev, H., Favaron, M., Vicini, S., et al. Glutamate-induced neuronal death in primary cultures of cerebellar granule cells: Protection by synthetic derivatives of endogenous sphingolipids. J. Pharmacol. Exp. Ther. 252(1), 419-427 (1990).

    3. Kobayashi, T., Goto, I., Okada, S., et al. Accumulation of lysosphingolipids in tissues from patients with GM1 and GM2 gangliosidoses. J. Neurochem. 59(4), 1452-1458 (1992).