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G7641

Sigma-Aldrich

Monosialoganglioside GM1 from bovine brain

≥95%, lyophilized powder

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Synonym(s):
Ganglioside GM1, monosialo
CAS Number:
NACRES:
NA.77

Quality Level

assay

≥95%

form

lyophilized powder

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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1 of 4

This Item
G9652G8397G3018
Quality Level

300

Quality Level

200

Quality Level

200

Quality Level

200

assay

≥95%

assay

≥95% (TLC)

assay

≥95% (TLC)

assay

~98%

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

Monosialoganglioside GM1 is a major sialoglycolipid of neuronal membranes.
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

Monosialoganglioside GM1 from bovine brain has been used:
  • in GM1 capture enzyme-linked immunosorbent assay (ELISA)
  • for the quantification of cholera toxin B subunit (CTB)-p277 protein accumulation
  • for Escherichia coli heat-labile enterotoxin (LT-B) detection
  • to determine the affinity of the GM1-ganglioside receptor for the plant-derived Escherichia coli heat-labile toxin LTK63 protein
Specific receptors for cholera toxin that accumulate in the brain in late infantile lipidosis.

Biochem/physiol Actions

Monosialoganglioside GM1 maintains calcium homeostasis, neurotrophic factor signaling, membrane integrity, and α-synuclein aggregation. It binds to the cholera toxin B subunit, leading to the activation of adenylate cyclase in a wide variety of cell types. The binding of cholera toxin to membrane-associated monosialoganglioside GM1 causes the translocation of A subunit of cholera toxin to the cell interior for the catalysis of ADP ribosylation. In addition, the binding of cholera toxin to monosialoganglioside GM1 causes translocation of nuclear factor (NF)-kB and activation of dendritic cells. Monosialoganglioside GM1 is effective in treating cerebral ischemia and dementia, stroke, and spinal cord injury in several in vivo and in vitro model systems. Accumulation of GM1, due to defective acid hydrolases, leads to GM1 gangliosidosis, which is a lethal lysosomal disease. It was also found to have a regulatory role in the formation of neurotoxic β-amyloid fibrils associated with Alzheimer′s disease and possible involvement in the pathogenesis of demyelination in relapsing-remitting multiple sclerosis.

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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Lilli Stergiou et al.
PloS one, 8(2), e55799-e55799 (2013-02-15)
Simian Virus 40 (SV40) is a paradigm pathogen with multivalent binding sites for the sphingolipid GM1, via which it induces its endocytosis for infection. Here we report that SV40 also utilizes cell surface integrins to activate signaling networks required for
Lorena Moeller et al.
Journal of experimental botany, 60(12), 3337-3352 (2009-06-06)
The Escherichia coli heat-labile enterotoxin B subunit (LT-B) has been used as a model antigen for the production of plant-derived high-valued proteins in maize. LT-B with its native signal peptide (BSP) has been shown to accumulate in starch granules of
Josephine F Reijneveld et al.
Proceedings of the National Academy of Sciences of the United States of America, 117(37), 22944-22952 (2020-09-02)
γδ T cells form an abundant part of the human cellular immune system, where they respond to tissue damage, infection, and cancer. The spectrum of known molecular targets recognized by Vδ1-expressing γδ T cells is becoming increasingly diverse. Here we
Satoshi Kuwabara et al.
The Lancet. Neurology, 12(12), 1180-1188 (2013-11-16)
Acute motor axonal neuropathy (AMAN) is a pure motor axonal subtype of Guillain-Barré syndrome (GBS) that was identified in the late 1990s. In Asia and Central and South America, it is the major subtype of GBS, seen in 30-65% of
Krystal Teasley Hamorsky et al.
PLoS neglected tropical diseases, 7(3), e2046-e2046 (2013-03-19)
Cholera toxin B subunit (CTB) is a component of an internationally licensed oral cholera vaccine. The protein induces neutralizing antibodies against the holotoxin, the virulence factor responsible for severe diarrhea. A field clinical trial has suggested that the addition of

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