G9652

Monosialoganglioside G_M1 from bovine brain

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

• Synonyme(s) : Ganglioside G_M1, monosialo
• Numéro CAS: 37758-47-7
• MDL number: MFCD00466936
• UNSPSC Code: 12352211
• NACRES: NA.75

Propriétés

• Quality Segment: 200
• 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

Description

General description

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.

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.

Informations sur la sécurité

• Classe de stockage: 11 - Combustible Solids
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)