11034-93-8
| Name | GB4 |
| CAS | 11034-93-8 |
| Molecular Formula | C56H102N2O23 |
| MDL Number | MFCD00131163 |
| MOL File | 11034-93-8.mol |
Synonyms
GB4
GL4
GLOBOSIDE
GBOSE4CER
GLOBOSIDES
CytolipinK
GlobosideI
GlobosideGL4
GangliosideGL4
Globosidicacid
Globosylceramide
Globosides (huMan)
GLOBOTETRAOSYLCERAMIDE
GLOBOTETRAOSYL CREAMIDE
GLOBOTETRAHEXOSYL-CERAMIDE
globosidefromhumanerythrocytes
Tetrahexosylceramide (d18:1/12:0)
Tetrahexosylceramide (d18:1/16:0)
Tetrahexosylceramide (d18:1/18:0)
Tetrahexosylceramide (d18:1/20:0)
Tetrahexosylceramide (d18:1/22:0)
Tetrahexosylceramide (d18:1/24:0)
Tetrahexosylceramide (d18:1/25:0)
Tetrahexosylceramide (d18:1/26:0)
Tetrahexosylceramide (d18:1/9Z-18:1)
Globotetraosylceramide (porcine RBC)
Globotetraosylceramides (porcine RBC)
Tetrahexosylceramide (d18:1/26:1(17Z))
Tetrahexosylceramide (d18:1/24:1(15Z))
GLOBOTETRAOSYLCERAMIDE, FROM PORCINE ERYTHROCYTE
N-acetyl-beta-D-galactosaminyl-(1->3)-alpha-D-galactosyl-(1->4)-beta-D-galactosyl-(1->4)-beta-D-glucosylceramide
Ceramide,1-O-[O-2-(acetylamino)-2-deoxy-β-D-galactopyranosyl-(1-)3)-O-α-D-galactopyranosyl-(1-)4)-O-β-D-galactopyranosyl-(1-)4)-β-D-glucopyranosyl]-
(Z)-1-O-[4-O-[4-O-[3-O-(2-Deoxy-2-acetylamino-β-D-glucopyranosyl)-α-D-galactopyranosyl]-β-D-galactopyranosyl]-β-D-glucopyranosyl]-N-(1-oxotetracosyl)-4-sphingenine
N-((2S,3R,E)-1-((2R,3R,4R,5S,6R)-5-((2S,3R,4R,5R,6R)-5-((2R,3R,4S,5S,6R)-4-((2S,3R,4R,5R,6R)-3-ethanamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3-hydroxyoctadec-4-en-2-yl)icosanamide
N-((2S,3R,E)-1-((2R,3R,4R,5S,6R)-5-((2S,3R,4R,5R,6R)-5-((2R,3R,4S,5S,6R)-4-((2S,3R,4R,5R,6R)-3-ethanamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3-hydroxyoctadec-4-en-2-yl)docosanamide
N-((2S,3R,E)-1-((2R,3R,4R,5S,6R)-5-((2S,3R,4R,5R,6R)-5-((2R,3R,4S,5S,6R)-4-((2S,3R,4R,5R,6R)-3-ethanamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3-hydroxyoctadec-4-en-2-yl)dodecanamide
N-((2S,3R,E)-1-((2R,3R,4R,5S,6R)-5-((2S,3R,4R,5R,6R)-5-((2R,3R,4S,5S,6R)-4-((2S,3R,4R,5R,6R)-3-ethanamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3-hydroxyoctadec-4-en-2-yl)octadecanamide
N-((2S,3R,E)-1-((2R,3R,4R,5S,6R)-5-((2S,3R,4R,5R,6R)-5-((2R,3R,4S,5S,6R)-4-((2S,3R,4R,5R,6R)-3-ethanamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3-hydroxyoctadec-4-en-2-yl)hexadecanamide
N-((2S,3R,E)-1-((2R,3R,4R,5S,6R)-5-((2S,3R,4R,5R,6R)-5-((2R,3R,4S,5S,6R)-4-((2S,3R,4R,5R,6R)-3-ethanamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3-hydroxyoctadec-4-en-2-yl)hexacosanamide
N-((2S,3R,E)-1-((2R,3R,4R,5S,6R)-5-((2S,3R,4R,5R,6R)-5-((2R,3R,4S,5S,6R)-4-((2S,3R,4R,5R,6R)-3-ethanamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3-hydroxyoctadec-4-en-2-yl)pentacosanamide
N-((2S,3R,E)-1-((2R,3R,4R,5S,6R)-5-((2S,3R,4R,5R,6R)-5-((2R,3R,4S,5S,6R)-4-((2S,3R,4R,5R,6R)-3-ethanamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3-hydroxyoctadec-4-en-2-yl)tetracosanamide
(Z)-N-((2S,3R,E)-1-((2R,3R,4R,5S,6R)-5-((2S,3R,4R,5R,6R)-5-((2R,3R,4S,5S,6R)-4-((2S,3R,4R,5R,6R)-3-ethanamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3-hydroxyoctadec-4-en-2-yl)octadec-9-enamide
(Z)-N-((2S,3R,E)-1-((2R,3R,4R,5S,6R)-5-((2S,3R,4R,5R,6R)-5-((2R,3R,4S,5S,6R)-4-((2S,3R,4R,5R,6R)-3-ethanamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3-hydroxyoctadec-4-en-2-yl)hexacos-17-enamide
(Z)-N-((2S,3R,E)-1-((2R,3R,4R,5S,6R)-5-((2S,3R,4R,5R,6R)-5-((2R,3R,4S,5S,6R)-4-((2S,3R,4R,5R,6R)-3-ethanamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3-hydroxyoctadec-4-en-2-yl)tetracos-15-enamide
Chemical Properties
| storage temp. | −20°C |
| solubility | Chloroform:Methanol (2:1): Soluble; DMSO: Soluble; Methanol: Warmed |
| form | A solid |
Hazard Information
Description
Globotetraosylceramides are bioactive neutral glycosphingolipids. They are the major glycolipids in human erythrocytes. They act as receptors for the Shiga toxins Stx1, Stx2, and Stx2e, the cytotoxic protein pierisin-1, and parvovirus B19. Globotetraosylceramides increase the expression of proteins responsible for enamel deposition, including ameloblastin, amelogenin, and enamelin, in dental epithelial cells and activate the ERK and p38 MAPK signaling pathways. Levels of globotetraosylceramides are elevated in fibroblasts from patients with salt and pepper syndrome, a neurocutaneous condition characterized by intellectual disability and hyper- and hypo-pigmented skin. Globotetraosylceramides (porcine RBC) contains a mixture of globotetraosylceramides with variable fatty acyl chain lengths isolated from porcine red blood cells. [Matreya, LLC. Catalog No. 1068]
Chemical Properties
White powder
Uses
Globotetraosylceramide (porcine RBC) is a biochemical reagent.
References
[1] T YAMAKAWA N K S YOKOYAMA. Structure of main globoside of human erythrocytes.[J]. Journal of biochemistry, 1962, 52: 228-229. DOI: 10.1093/oxfordjournals.jbchem.a127603
[2] J. MüTHING. Shiga toxins, glycosphingolipid diversity, and endothelial cell injury[J]. Thrombosis and haemostasis, 2009, 101 1: 252-264. DOI: 10.1160/th08-05-0317
[3] YUKO MATSUSHIMA-HIBIYA. Identification of glycosphingolipid receptors for pierisin-1, a guanine-specific ADP-ribosylating toxin from the cabbage butterfly.[J]. The Journal of Biological Chemistry, 2003, 278 11: 9972-9978. DOI: 10.1074/jbc.m212114200
[4] WAQAS NASIR . Parvovirus B19 VLP recognizes globoside in supported lipid bilayers[J]. Virology, 2014, 456: Pages 364-369. DOI: 10.1016/j.virol.2014.04.004
[5] TAKASHI NAKAMURA. Globoside accelerates the differentiation of dental epithelial cells into ameloblasts[J]. International Journal of Oral Science, 2016, 8 4: 205-212. DOI: 10.1038/ijos.2016.35
[6] LUIGI BOCCUTO. A mutation in a ganglioside biosynthetic enzyme, ST3GAL5, results in salt & pepper syndrome, a neurocutaneous disorder with altered glycolipid and glycoprotein glycosylation.[J]. Human molecular genetics, 2014, 23 2: 418-433. DOI: 10.1093/hmg/ddt434
[2] J. MüTHING. Shiga toxins, glycosphingolipid diversity, and endothelial cell injury[J]. Thrombosis and haemostasis, 2009, 101 1: 252-264. DOI: 10.1160/th08-05-0317
[3] YUKO MATSUSHIMA-HIBIYA. Identification of glycosphingolipid receptors for pierisin-1, a guanine-specific ADP-ribosylating toxin from the cabbage butterfly.[J]. The Journal of Biological Chemistry, 2003, 278 11: 9972-9978. DOI: 10.1074/jbc.m212114200
[4] WAQAS NASIR . Parvovirus B19 VLP recognizes globoside in supported lipid bilayers[J]. Virology, 2014, 456: Pages 364-369. DOI: 10.1016/j.virol.2014.04.004
[5] TAKASHI NAKAMURA. Globoside accelerates the differentiation of dental epithelial cells into ameloblasts[J]. International Journal of Oral Science, 2016, 8 4: 205-212. DOI: 10.1038/ijos.2016.35
[6] LUIGI BOCCUTO. A mutation in a ganglioside biosynthetic enzyme, ST3GAL5, results in salt & pepper syndrome, a neurocutaneous disorder with altered glycolipid and glycoprotein glycosylation.[J]. Human molecular genetics, 2014, 23 2: 418-433. DOI: 10.1093/hmg/ddt434
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