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G3767

Sigma-Aldrich

Trisialoganglioside-GT1b from bovine brain

lyophilized powder, ≥96% (TLC)

Synonym(s):

Ganglioside GT1b

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About This Item

CAS Number:
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

assay

≥96% (TLC)

form

lyophilized powder

solubility

DMSO: soluble
ethanol: soluble

storage temp.

−20°C

InChI

1S/C88H157N5O44/c1-4-6-8-10-12-14-16-18-19-21-23-25-27-29-31-33-56(107)92-37-51(45(101)32-30-28-26-24-22-20-17-15-13-11-9-7-5-2)124-80-66(113)65(112)70(54(42-98)127-80)129-82-69(116)77(136-87(84(120)121)35-46(102)57(89)72(132-87)61(108)49(105)38-94)71(55(43-99)128-82)130-79-60(93-44(3)100)75(63(110)52(40-96)125-79)131-81-68(115)76(64(111)53(41-97)126-81)135-86(83(118)119)34-47(103)59(91)74(134-86)67(114)78(117)137-88(85(122)123)36-48(104)58(90)73(133-88)62(109)50(106)39-95/h30,32,45-55,57-82,94-99,101-106,108-117H,4-29,31,33-43,89-91H2,1-3H3,(H,92,107)(H,93,100)(H,118,119)(H,120,121)(H,122,123)/b32-30+/t45?,46-,47-,48-,49?,50?,51?,52-,53-,54+,55-,57+,58+,59+,60-,61?,62?,63+,64+,65+,66+,67?,68-,69-,70+,71+,72+,73+,74+,75-,76+,77-,78?,79+,80+,81+,82+,86+,87+,88+/m0/s1

InChI key

NVNPEYQWKCQBBU-ADMXJUBYSA-N

Amino Acid Sequence

Cer-Glc-Gal(NeuAc-NeuAc)-GalNAc-Gal-NeuAc

General description

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

Trisialoganglioside-GT1b from bovine brain has been used:
  • in high performance thin layer chromatography (HPTLC)[1]
  • in membrane GM1 assays[2]
  • as reference standards for TLC (thin layer chromatography) and as antigens for ELISA (enzyme-linked immunosorbent assay)[3]

Biochem/physiol Actions

Ganglioside marker for metastatic brain tumors. Modulates cellular differentiation; prevents glutamate neurotoxicity; inhibits mitogenesis stimulated by lectins such as Con A. Converted to GD1b by bacterial and mammalian sialidases.

Analysis Note

Homogeneous aqueous preparations can be obtained by suspending the compound in water, buffer or cell culture medium and sonicating briefly to facilitate the micelle formation.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Membrane lipid composition and its physicochemical properties define cell vulnerability to aberrant protein oligomers
Evangelisti E, et al.
Journal of Cell Science, 324(1), jcs-098434 (2012)
Endogenous immune response to gangliosides in patients with confined prostate cancer
Ravindranath M H, et al.
International Journal of Cancer. Journal International Du Cancer, 116(3), 368-377 (2005)
Shun Watanabe et al.
Pain, 152(2), 327-334 (2010-12-08)
Gangliosides are abundant in neural tissue and play important roles in cell-cell adhesion, signal transduction, and cell differentiation. Gangliosides are divided into 4 groups: asialo-, a-, b-, and c-series gangliosides, based on their biosynthetic pathway. St8sia1 knockout mice, which lack
Sureshkumar Venkateshwari et al.
Journal of biomolecular structure & dynamics, 30(3), 255-268 (2012-07-04)
The conformational property of oligosaccharide GT1B in aqueous environment was studied by molecular dynamics (MD) simulation using all-atom model. Based on the trajectory analysis, three prominent conformational models were proposed for GT1B. Direct and water-mediated hydrogen bonding interactions stabilize these
H Hamasaki et al.
Biochimica et biophysica acta, 1437(1), 93-99 (1999-02-05)
We studied ganglioside expression in 12 human metastatic brain tumors metastasized from colon (4), renal (3), lung (2), esophagus (1), pancreas (1), and mammary (1) carcinomas. GM3 was the major common ganglioside expressed in brain metastatic tumor tissues, and GT1b

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