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G9652

Sigma-Aldrich

Monosialoganglioside GM1 from bovine brain

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

Synonyme(s) :

Ganglioside GM1, monosialo

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About This Item

Numéro CAS:
37758-47-7
Code UNSPSC :
12352211
Nomenclature NACRES :
NA.75

Niveau de qualité

200

Stérilité

γ-irradiated

Gamme de produits

BioXtra

Pureté

≥95% (TLC)

Forme

lyophilized powder

Poids mol.

~1540

Technique(s)

blocking: suitable

Impuretés

endotoxin, tested

Solubilité

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

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

CNLVNZJJSHZYAS-ALSOZVJRSA-N

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Amino Acid Sequence

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

Description générale

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.
Les gangliosides sont des constituants majeurs des membranes cellulaires neuronales et du réticulum endoplasmique. Ils contiennent une chaîne de polysaccharide à groupes sialate liés au céramide par une liaison β-glycosidique. Pour consulter une classification des gangliosides voir Svennerholm, L., et al. (eds.), Structure and Function of Gangliosides, New York, Plenum, 1980.

Application

Récepteurs spécifiques de la toxine cholérique qui s'accumulent dans le cerveau dans la lipidose infantile tardive.

Actions biochimiques/physiologiques

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.

Notes préparatoires

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Tobias Gustafsson et al.
European journal of immunology, 43(7), 1779-1788 (2013-05-08)
Cholera toxin (CT) binds to GM1-ganglioside receptors present on all nucleated cells. Despite this, it is a very potent mucosal adjuvant that has a dramatic impact on immune cells, as well as nerve and epithelial cells, causing diarrhea. This fact
Eduardo Nobile-Orazio et al.
Journal of neurology, neurosurgery, and psychiatry, 85(7), 754-758 (2013-08-03)
Increased titres of serum IgM antibodies to GM1 ganglioside are often associated with multifocal motor neuropathy (MMN). Testing for IgM antibodies to other antigens including GM2, the mixture of GM1 and galactocerebroside (GM1/GalC) and the disulfated heparin disaccharide NS6S were
Michael G Jobling et al.
mBio, 3(6), doi:10-doi:10 (2012-11-01)
Cholera toxin (CT) from Vibrio cholerae is responsible for the majority of the symptoms of the diarrheal disease cholera. CT is a heterohexameric protein complex with a 240-residue A subunit and a pentameric B subunit of identical 103-residue B polypeptides.
Carol J Cox et al.
Journal of immunology (Baltimore, Md. : 1950), 191(11), 5524-5541 (2013-11-05)
How autoantibodies target the brain and lead to disease in disorders such as Sydenham chorea (SC) is not known. SC is characterized by autoantibodies against the brain and is the main neurologic manifestation of streptococcal-induced rheumatic fever. Previously, our novel
Djurre H de Jong et al.
Faraday discussions, 161, 347-363 (2013-06-29)
We present results from coarse grain molecular dynamics simulations of mixed model membranes consisting of saturated and unsaturated lipids together with cholesterol, in which lipid-anchored membrane proteins are embedded. The membrane proteins studied are the peripherally bound H-Ras, N-Ras, and
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