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G3018

Asialoganglioside GM

Name: Asialoganglioside GM
Brand: SIGMA

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

Assay:

~98%

Form:

lyophilized powder

Quality level:

200

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Product Name

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

assay

~98%

Quality Level

200

form

lyophilized powder

storage temp.

−20°C

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

Related Categories

Bioactive Small Molecules

Biochemicals

Glycoconjugates

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

0000445534

0000420478

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Analysis of a cholera toxin B subunit (CTB) and human mucin 1 (MUC1) conjugate protein in a MUC1-tolerant mouse model.

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

Differential regulation of GM1 and asialo-GM1 expression by T cells and natural killer (NK) cells in respiratory syncytial virus infection.

Martin L Moore et al.

Viral immunology, 21(3), 327-339 (2008-09-16)

We previously reported that respiratory syncytial virus (RSV) infection increases lung CD8(+) T cell GM1 expression. The related lipid asialo-GM1 (ASGM1) is expressed by T cells in viral infection and by natural killer (NK) cells. The in vivo co-expression of

NK cell-depleting anti-asialo GM1 antibody exhibits a lethal off-target effect on basophils in vivo.

Hideto Nishikado et al.

Journal of immunology (Baltimore, Md. : 1950), 186(10), 5766-5771 (2011-04-15)

NK cells are innate immune lymphocytes and play a key role in both innate and adaptive immunity. Their pivotal functions in vivo have been illustrated in mice by means of their ablation with NK cell-depleting Abs, particularly anti-asialo GM1 (ASGM1).

Combination treatment with IL-2 and anti-IL-2 mAbs reduces tumor metastasis via NK cell activation.

Gui-Hua Jin et al.

International immunology, 20(6), 783-789 (2008-05-02)

Combination treatment consisting of IL-2 together with anti-IL-2 mAbs results in markedly larger increases in the numbers of CD8(+) T cells, dendritic cells (DCs) and NK cells in vivo compared with the results observed with injections of IL-2 or the

Near-field scanning optical microscopy detects nanoscale glycolipid domains in the plasma membrane.

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

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Global Trade Item Number

SKU	GTIN
G3018-1MG	04061833629659
G3018-.5MG	04061833420751

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