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G8397

Monosialoganglioside G_M2 from bovine brain

Name: Monosialoganglioside G<SUB>M2</SUB> from bovine brain
Brand: SIGMA

≥95% (TLC), lyophilized powder

Synonym(s):

Ganglioside G_M2, monosialo

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About This Item

CAS Number:

19600-01-2

UNSPSC Code:

12352200

NACRES:

NA.77

MDL number:

MFCD00131137

Assay:

≥95% (TLC)

Quality level:

200

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Properties

Product Name

Monosialoganglioside G_M2 from bovine brain, ≥95% (TLC)

Quality Level

200

assay

≥95% (TLC)

storage temp.

−20°C

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

Description

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.

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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