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G8397

Monosialoganglioside GM2 from bovine brain

≥95% (TLC), lyophilized powder

Synonym(s):

Ganglioside GM2, monosialo

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About This Item

CAS Number:
19600-01-2
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD00131137

Product Name

Monosialoganglioside GM2 from bovine brain, ≥95% (TLC)

SMILES string

N([C@@H]1[C@H](O[C@H]([C@H]([C@H]1O)O)CO)O[C@@H]2[C@@H](O[C@@H]([C@H]([C@@H]2OC[C@@]4(O[C@@H]([C@H]([C@@H](C4)O)NC(=O)C)[C@@H](O)[C@@H](O)CO)C(=O)O)O)O[C@H]3[C@@H](O[C@H]([C@H]([C@@H]3O)O)OC[C@@H](NC(=O)CCCCCCCCCCCCCCCCC)[C@@H](O)\C=C\CCCCCCCCCCCCC)CO)CO)

InChI

1S/C68H123N3O26/c1-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-51(81)71-44(45(78)33-31-29-27-25-23-21-18-16-14-12-10-8-6-2)40-90-65-58(86)57(85)60(49(38-74)93-65)95-66-59(87)63(61(50(39-75)94-66)96-64-53(70-43(4)77)56(84)55(83)48(37-73)92-64)91-41-68(67(88)89)35-46(79)52(69-42(3)76)62(97-68)54(82)47(80)36-72/h31,33,44-50,52-66,72-75,78-80,82-87H,5-30,32,34-41H2,1-4H3,(H,69,76)(H,70,77)(H,71,81)(H,88,89)/b33-31+/t44-,45+,46-,47+,48+,49+,50+,52+,53+,54+,55-,56+,57+,58+,59+,60+,61-,62+,63+,64-,65-,66-,68-/m1/s1

InChI key

USMMPBVNWHAJBE-YMEOXFOQSA-N

assay

≥95% (TLC)

storage temp.

−20°C

Quality Level

200

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Application

Monosialoganglioside GM2 from bovine brain has been used:
  • to study the effects of GM2 supplementation and depletion of all cellular ganglioside subspecies on neurite outgrowth and neuronal survival using canine dorsal root ganglia (DRG) neurons
  • as a reference standard for high-performance thin-layer chromatography (HPTLC) and as antigens for enzyme-linked immunosorbent assay (ELISA) to analyze the ganglioside signatures of human prostate cancer (CaP) cells
  • as a component of the reaction buffer to perform in vitro activity assay of GM1 synthase

Biochem/physiol Actions

Ganglioside GM2 (GM2) is one of the critical components of the cell membrane and is essential for cell signaling and metabolism. Various studies show the involvement of gangliosides in cancer, serotype 1 reovirus infection, and insulin secretion and regulation. GM2 exhibits a protective role by associating with the adhesion, motility, and proliferation in tumor cells. Decreased expression of GM2 indicates extensive cancer malignancy. GM2 serves as a receptor for reovirus strain type 1 Lang (T1L). Abnormal regulation of GM2 has been observed in several diseases associated with the nervous system.

General description

Ganglioside GM2 (GM2), a monosialic ganglioside, belongs to the group of glycosphingolipids that are mostly localized to the outer leaflet of the plasma membrane. Gangliosides are amphipathic molecules containing a head group (modified by carbohydrates) with a negative charge. The carbohydrate groups vary from species to species. GM2 is predominantly expressed in the neural tissues.
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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000490225
0000490225
0000447999
0000447999
0000401632

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M Sorice et al.
Bioscience reports, 19(3), 197-208 (1999-10-08)
In this study we analyzed by immunofluorescence, laser confocal microscopy, immunoelectron microscopy and label fracture technique the ganglioside distribution on the plasma membrane of several different cell types: human peripheral blood lymphocytes (PBL), Molt-4 lymphoid cells, and NIH 3T3 fibroblasts
H C Yohe et al.
Glycobiology, 7(8), 1215-1227 (1998-02-10)
Sialoglycosphingolipids (gangliosides) have been increasingly implicated as regulators of membrane signaling events. Macrophage ganglioside patterns dramatically increase in complexity when murine peritoneal macrophages are stimulated in vivo with the appearance of the sialidase-sensitive monosialoganglioside GM1b (cisGM1) as a major component.
K Nohara et al.
Breast cancer research and treatment, 48(2), 149-157 (1998-05-22)
Much evidence has shown that glycosphingolipids are involved in cellular recognition, regulation of cell growth, and metastasis. In the present study, the major glycosphingolipids of two widely studied human breast cancer cell lines were examined. The MCF-7 cell line has
Angie Rupp et al.
Journal of the peripheral nervous system : JPNS, 18(1), 75-88 (2013-03-26)
Acute canine polyradiculoneuritis (ACP) is considered to be the canine equivalent of the human peripheral nerve disorder Guillain-Barré syndrome (GBS); an aetiological relationship, however, remains to be demonstrated. In GBS, anti-glycolipid antibodies (Abs) are considered as important disease mediators. To
Mitsuo Saito et al.
Journal of neurochemistry, 121(4), 649-661 (2012-03-01)
GM2 ganglioside in the brain increased during ethanol-induced acute apoptotic neurodegeneration in 7-day-old mice. A small but a significant increase observed 2 h after ethanol exposure was followed by a marked increase around 24 h. Subcellular fractionation of the brain
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Product Information Sheet - G8397

Product Information Sheet

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