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G3018

Asialoganglioside GM

from bovine brain, ~98%, cholera toxin inhibitor, lyophilized powder

Synonym(s):

Ceramide tetrahexoside, Ganglioside GM1, asialo, Gangliotetraosyl ceramide

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About This Item

CAS Number:
71012-19-6
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD00131128

Key Documents

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Product Name

Asialoganglioside GM1 from bovine brain, ~98%, lyophilized powder

SMILES string

N([C@H]1[C@@H](O[C@@H]([C@@H]([C@@H]1O[C@@H]4O[C@@H]([C@@H]([C@@H]([C@H]4O)O)O)CO)O)CO)O[C@H]2[C@H](O[C@H]([C@@H]([C@H]2O)O)O[C@@H]3[C@H](OC([C@@H]([C@H]3O)O)OCC(NC(=O)CCCCCCCCCCCCCCCCC)C(O)\C=C\CCCCCCCCCCCCC)CO)CO)C(=O)C

InChI

1S/C62H114N2O23/c1-4-6-8-10-12-14-16-18-19-21-23-25-27-29-31-33-46(71)64-40(41(70)32-30-28-26-24-22-20-17-15-13-11-9-7-5-2)38-80-60-54(78)51(75)57(44(36-67)83-60)86-62-55(79)52(76)56(45(37-68)84-62)85-59-47(63-39(3)69)58(49(73)43(35-66)81-59)87-61-53(77)50(74)48(72)42(34-65)82-61/h30,32,40-45,47-62,65-68,70,72-79H,4-29,31,33-38H2,1-3H3,(H,63,69)(H,64,71)/b32-30+/t40?,41?,42-,43-,44-,45-,47-,48+,49+,50+,51-,52-,53-,54-,55-,56+,57-,58-,59+,60?,61+,62+/m1/s1

InChI key

VELGMVLNORPMAO-JTFNWEOFSA-N

assay

~98%

form

lyophilized powder

storage temp.

−20°C

Quality Level

200

Related Categories

General description

Gangliosides are major constituents of neuronal cell membranes and endoplasmic reticulum; contain a sialylated 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.

Biochem/physiol Actions

Removing the sialic acid from monosialoganglioside GM1 inhibits its ability to bind cholera toxin. Asialoganglioside GM1 does not block the binding of cholera toxin to cellular GM1.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000496866
0000496866
0000445534
0000445534
0000420478

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Julia Pinkhasov et al.
Cancer immunology, immunotherapy : CII, 59(12), 1801-1811 (2010-09-09)
Since epithelial mucin 1 (MUC1) is associated with several adenocarcinomas at the mucosal sites, it is pertinent to test the efficacy of a mucosally targeted vaccine formulation. The B subunit of the Vibrio cholerae cholera toxin (CTB) has great potential
Pawel R Kiela et al.
Gastroenterology, 137(3), 965-975 (2009-05-20)
NHE3 is a target of inhibition by proinflammatory cytokines and pathogenic bacteria, an event contributing to diarrhea in infectious and idiopathic colitis. In mice, NHE3 deficiency leads to mild diarrhea, increased intestinal expression of interferon (IFN)-gamma, and distal colitis, suggesting
A Abulrob et al.
Journal of microscopy, 232(2), 225-234 (2008-11-20)
The localization of asialo-GM1 in ordered membrane raft domains in HeLa cells has been examined using a combination of membrane fractionation and fluorescence imaging. The glycolipid is enriched in Triton X-100 insoluble membrane fractions that contain high concentrations of cholesterol
A K Sheikhi et al.
Pakistan journal of biological sciences : PJBS, 10(17), 2885-2889 (2007-09-01)
Specialized lymphocytes, called uterine Natural Killer (uNK) cells, appear in human and rodent uteri and become abundant at implantation sites during decidualization and early pregnancy. The hallmark of human uNK cells is intense expression of CD56, a neural cell adhesion
Lindsay J Hall et al.
Journal of immunology (Baltimore, Md. : 1950), 184(8), 4327-4337 (2010-03-12)
NK cells were found to be recruited in a temporally controlled manner to the nasal-associated lymphoid tissue and the cervical lymph nodes of mice after intranasal immunization with Ag85B-early secreted antigenic target 6 kDa from Mycobacterium tuberculosis mixed with Escherichia
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