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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:
59247-13-1
MDL number:
MFCD00081622
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

200

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)
  • in membrane GM1 assays
  • as reference standards for TLC (thin layer chromatography) and as antigens for ELISA (enzyme-linked immunosorbent assay)

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 Code

11 - Combustible Solids

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Gangliosides as cell surface receptors and transducers of biological signals.
Fishman
New Trends in Ganglioside Research, 14, 219-219 (1988)
Seung T Lim et al.
Neuropharmacology, 60(7-8), 1160-1167 (2010-10-26)
Gangliosides are lipophilic compounds found in cell plasma membranes throughout the brain that play a role in neuronal plasticity and regeneration. Indeed, absence or abnormal accumulation of gangliosides has been shown to lead to neurological disorders. Experimental data have shown
Gangliosides of organ-confined versus metastatic androgen-receptor-negative prostate cancer
Ravindranath M H, et al.
Biochemical and Biophysical Research Communications, 324(1), 154-165 (2004)
Patricia Urbina et al.
Biochimica et biophysica acta, 1808(1), 279-286 (2010-08-24)
α-Toxin, a major determinant of Clostridium perfringens toxicity, exhibits both phospholipase C and sphingomyelinase activities. Our studies with large unilamellar vesicles containing a variety of lipid mixtures reveal that both lipase activities are enhanced by cholesterol and by lipids with
Amanda Przedpelski et al.
Infection and immunity, 81(7), 2638-2644 (2013-05-15)
The need for a vaccine against botulism has increased since the discontinuation of the pentavalent (ABCDE) botulinum toxoid vaccine by the Centers for Disease Control and Prevention. The botulinum toxins (BoNTs) are the primary virulence factors and vaccine components against
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