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Merck
CN

G9652

Sigma-Aldrich

Monosialoganglioside GM1 from bovine brain

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

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别名:
Ganglioside GM1, monosialo
CAS号:
UNSPSC代码:
12352211
NACRES:
NA.75

质量水平

无菌性

γ-irradiated

产品线

BioXtra

检测方案

≥95% (TLC)

形式

lyophilized powder

分子量

~1540

技术

blocking: suitable

杂质

endotoxin, tested

溶解性

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

储存温度

−20°C

SMILES字符串

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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Amino Acid Sequence

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

一般描述

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.

应用

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

生化/生理作用

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.

制备说明

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.

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)


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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
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
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
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
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.

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