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G7641

Sigma-Aldrich

Monosialoganglioside GM1 from bovine brain

≥95% (TLC), lyophilized powder, sialoglycolipid

Synonym(s):

Ganglioside GM1, monosialo

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About This Item

CAS Number:
37758-47-7
UNSPSC Code:
12352200
NACRES:
NA.77

product name

Monosialoganglioside GM1 from bovine brain, ≥95%, lyophilized powder

Quality Level

300

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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Related Categories

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.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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
Adam Shahine et al.
Nature communications, 10(1), 56-56 (2019-01-06)
CD1 proteins are expressed on dendritic cells, where they display lipid antigens to T-cell receptors (TCRs). Here we describe T-cell autoreactivity towards ubiquitous human membrane phospholipids presented by CD1b. These T-cells discriminate between two major types of lipids, sphingolipids and
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
Henry Daniell et al.
Plant biotechnology journal, 17(7), 1357-1368 (2018-12-24)
To prevent vaccine-associated paralytic poliomyelitis, WHO recommended withdrawal of Oral Polio Vaccine (Serotype-2) and a single dose of Inactivated Poliovirus Vaccine (IPV). IPV however is expensive, requires cold chain, injections and offers limited intestinal mucosal immunity, essential to prevent polio
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
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