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G8397

Sigma-Aldrich

Monosialoganglioside GM2 from bovine brain

≥95% (TLC)

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Synonym(s):
Ganglioside GM2, monosialo
CAS Number:
19600-01-2
MDL number:
MFCD00131137
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

200

Assay

≥95% (TLC)

storage temp.

−20°C

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

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Amino Acid Sequence

Cer-Glc-Gal(NeuAc)-GalNAc

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.

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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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.
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
K Klisch et al.
Reproduction (Cambridge, England), 142(5), 667-674 (2011-09-08)
Spermatogonia are a potential source of adult pluripotent stem cells and can be used for testis germ cell transplantation. Markers for the isolation of these cells are of great importance for biomedical applications. Primordial germ cells and prepubertal spermatogonia in
Fengyi Liu et al.
International journal of biological sciences, 8(8), 1085-1096 (2012-09-20)
Insect β-N-acetyl-D-hexosaminidases with broad substrate-spectrum (IBS-Hex) are the homologues of human β-N-acetyl-D-hexosaminidase A/B (HsHex A/ B). These enzymes are distributed in most insect species and vary in physiological roles. In this study, the gene encoding an IBS-Hex, OfHEX2, was cloned
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