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G9652

Sigma-Aldrich

Monosialoganglioside GM1 from bovine brain

lyophilized powder, BioXtra, γ-irradiated, ≥95% (TLC)

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Synonym(s):
Ganglioside GM1, monosialo
CAS Number:
NACRES:
NA.75

Quality Level

sterility

γ-irradiated

product line

BioXtra

assay

≥95% (TLC)

form

lyophilized powder

mol wt

~1540

technique(s)

blocking: suitable

impurities

endotoxin, tested

solubility

chloroform/methanol: 9.80-10.20 mg/mL, clear to slightly hazy, colorless to light yellow

storage temp.

−20°C

SMILES string

CCCCCCCCCCCCCCCCCCCC(=O)N[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O[C@@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)[C@H]3NC(C)=O)[C@H](O[C@@]5(C[C@H](O)[C@@H](NC(C)=O)[C@@H](O5)[C@H](O)[C@H](O)CO)C(O)=O)[C@H]2O)[C@H](O)[C@H]1O)[C@@H](O)\C=C\CCCCCCCCCCCCCCC

InChI

1S/C73H131N3O31/c1-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-52(86)76-44(45(83)33-31-29-27-25-23-21-18-16-14-12-10-8-6-2)40-99-69-61(93)59(91)63(50(38-79)102-69)104-71-62(94)67(98-41-47(85)55(87)66-53(74-42(3)81)46(84)35-73(97,107-66)72(95)96)64(51(39-80)103-71)105-68-54(75-43(4)82)65(57(89)49(37-78)100-68)106-70-60(92)58(90)56(88)48(36-77)101-70/h31,33,44-51,53-71,77-80,83-85,87-94,97H,5-30,32,34-41H2,1-4H3,(H,74,81)(H,75,82)(H,76,86)(H,95,96)/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

InChI key

CNLVNZJJSHZYAS-ALSOZVJRSA-N

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This Item
G7641G8397G3767
assay

≥95% (TLC)

assay

≥95%

assay

≥95% (TLC)

assay

≥96% (TLC)

form

lyophilized powder

form

lyophilized powder

form

-

form

lyophilized powder

solubility

chloroform/methanol: 9.80-10.20 mg/mL, clear to slightly hazy, colorless to light yellow

solubility

-

solubility

-

solubility

DMSO: soluble, ethanol: soluble

Quality Level

200

Quality Level

300

Quality Level

200

Quality Level

200

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

Amino Acid Sequence

Cer-Glc-Gal(NeuAc)-GalNAc-Gal

General description

Gangliosides are major constituents of neuronal cell membranes and endoplasmic reticulum. They contain a sialated polysaccharide chain linked to ceramide through a β-glycosidic linkage.
Gangliosides are major constituents of neuronal cell membranes and endoplasmic reticulum. They contain a sialated polysaccharide chain linked to ceramide through a β-glycosidic linkage. For classification of gangliosides see Svennerholm, L., et al. (eds.), Structure and Function of Gangliosides, New York, Plenum, 1980.

Application

Specific receptors for cholera toxin that accumulate in the brain in late infantile lipidosis.

Biochem/physiol Actions

Monosialoganglioside GM1 is a major sialoglycolipid of neuronal membranes that modulates calcium homeostasis. It binds to cholera toxin B subunit, resulting in stimulation of adenylate cyclase in a wide variety of cell types. After cholera toxin binds to membrane associated monosialoganglioside GM1, the A subunit of cholera toxin is translocated to the cell interior, where it catalyzes the ADP ribosylation of the membrane associated Gs subunit of adenylate cyclase. In addition, binding of cholera toxin to monosialoganglioside GM1 causes translocation of NF-κB and activation of dendritic cells.

Monosialoganglioside GM1 was one of many mono- and oligosaccharide ligands studied for their affinity for NKR-P1, a membrane protein on natural killer cells, which contains an extracellular Ca2+-dependent lectin domain. Monosialoganglioside GM1 is effective in partially correcting the consequences of neuroinjury in a number of in vivo and in vitro model systems.

Preparation Note

Monosialoganglioside GM1 is prepared by a modification of a published procedure. It is isolated from bovine brain by extraction and solvent fractionation methods. The final purification is done by HPLC on silica gel allowing no buffer salts to be used for the purification.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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