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860076W

Avanti

C18:0 GM1-d5

Avanti Research™ - A Croda Brand 860076W, methanol solution

Synonym(s):

C18:0 GM1 Ganglioside-d5 (synthetic, ammonium salt)

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About This Item

Empirical Formula (Hill Notation):
C73H129D5N4O31
CAS Number:
2260669-93-8
Molecular Weight:
1568.88
UNSPSC Code:
12352211
NACRES:
NA.25

assay

>99% (TLC)

form

methanol solution

packaging

pkg of 1 × 1 mL (860076W-100ug)

manufacturer/tradename

Avanti Research™ - A Croda Brand 860076W

concentration

0.1 mg/mL

shipped in

dry ice

storage temp.

−20°C

SMILES string

[H][C@](/C=C/CCCCCCCCCCCCC)(O)[C@@]([H])(NC(CCCCCCCCCCCCCCCC([2H])(C([2H])([2H])[2H])[2H])=O)CO[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H]([C@H](O[C@@]3(C([O-])=O)O[C@@H]([C@H](O)[C@H](O)CO)[C@@](NC(C)=O)([H])[C@@H](O)C3)[C@H]2O)O[C@@H]4O[C@H](C

General description

Gangliosides are glycosphingolipids, contains one or more residues of sialic acid. They are grouped according to the number of their sialic acid residues: one (M), two (D), or three (T). The GM1 ganglioside denotes a glycolipid that contains a monosialylated tetraose oligosaccharide (Galβ1 & 3GalNAcβ1 & 4(NeuAcα2 & 3)Galβ1 & 4Glcβ1 & 1′Cer). C18:0 GM1 ganglioside contains stearic acid as one of the fatty acid chain. These are normal components of the plasma membranes of mammalian cells and are abundant in neuronal membranes. Structurally, they possess the oligosaccharide chain constituting the hydrophilic portion in the extracellular medium and the ceramide moiety constituting the hydrophobic portion in the lipid layer of the membrane. The length and degree of unsaturation of both alkyl chains present in the ganglioside influences membrane fluidity and permeability. The ceramide portion regulates the activity of membrane-associated proteins.

Biochem/physiol Actions

Gangliosides plays an important role in cell-cell recognition, cell adhesion, contact inhibition, and tissue differentiation. GM1 ganglioside binds the cholera toxin.

Packaging

2 mL Amber Glass Sealed Ampule

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Flam. Liq. 2 - STOT SE 1

target_organs

Eyes,Central nervous system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

49.5 °F

flash_point_c

9.7 °C

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Cyclic AMP accumulation in HeLa cells induced by cholera toxin. Involvement of the ceramide moiety of GM1 ganglioside.
Masserini M, et al.
The Biochemical Journal, 271(1), 107-111 (1990)
Preparation of GM1 ganglioside molecular species having homogeneous fatty acid and long chain base moieties.
Sonnino S, et al.
Journal of Lipid Research, 26(2), 248-257 (1985)
Structural characterization of the GM1 ganglioside by infrared multiphoton dissociation, electron capture dissociation, and electron detachment dissociation electrospray ionization FT-ICR MS/MS.
McFarland MA, et al.
Journal of the American Society For Mass Spectrometry, 16(5), 752-762 (2005)

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