82005-99-0

Basic information

• Product Name: (2S,3R,4E)-2-(Tetracosanoylamino)-1-[4-O-(4-O-α-D-galactopyranosyl-β-D-galactopyranosyl)-β-D-glucopyranosyloxy]-4-octadecen-3-ol
• Synonyms: (2S,3R,4E)-2-(Tetracosanoylamino)-1-[4-O-(4-O-α-D-galactopyranosyl-β-D-galactopyranosyl)-β-D-glucopyranosyloxy]-4-octadecen-3-ol
• CAS NO: 82005-99-0
• Molecular Formula: C60H113NO18
• Molecular Weight: 1136.53512
• Mol File: 82005-99-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2S,3R,4E)-2-(Tetracosanoylamino)-1-[4-O-(4-O-α-D-galactopyranosyl-β-D-galactopyranosyl)-β-D-glucopyranosyloxy]-4-octadecen-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4E)-2-(Tetracosanoylamino)-1-[4-O-(4-O-α-D-galactopyranosyl-β-D-galactopyranosyl)-β-D-glucopyranosyloxy]-4-octadecen-3-ol(82005-99-0)
• EPA Substance Registry System: (2S,3R,4E)-2-(Tetracosanoylamino)-1-[4-O-(4-O-α-D-galactopyranosyl-β-D-galactopyranosyl)-β-D-glucopyranosyloxy]-4-octadecen-3-ol(82005-99-0)

Safety Data

• Hazardous Substances Data: 82005-99-0(Hazardous Substances Data)

Upstream product

• 557-59-5 n-tetracosanoic acid 
• 126550-86-5 globotriaosylsphingosine 
• 113421-50-4 O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1-4)-O-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1-4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1-1)-(2S,3R,4E)-3-O-benzoyl-2-N-tetracosanoylsphingenine 
• 113421-50-4 O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1-4)-O-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1-4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1-1)-(2S,3R,4Z)-3-O-benzoyl-2-N-tetracosanoylsphingenine 

Relevant articles and documents

Determination of globotriaosylceramide analogs in the organs of a mouse model of Fabry disease

Fabry disease is a heritable lipid disorder caused by the low activity of α-galactosidase A and characterized by the systemic accumulation of globotriaosylceramide (Gb3). Recent studies have reported a structural heterogeneity of Gb3 in Fabry disease, including Gb3 isoforms with different fatty acids and Gb3 analogs with modifications on the sphingosine moiety. However, Gb3 assays are often performed only on the selected Gb3 isoforms. To precisely determine the total Gb3 concentration, here we established two methods for determining both Gb3 isoforms and analogs. One was the deacylation method, involving Gb3 treatment with sphingolipid ceramide N-deacylase, followed by an assay of the deacylated products, globotriaosylsphingosine (lyso-Gb3) and its analogs, by ultra-performance LC coupled to tandem MS (UPLC-MS/MS). The other method was a direct assay established in the present study for 37 Gb3 isoforms and analogs/isoforms by UPLC-MS/MS. Gb3s from the organs of symptomatic animals of a Fabry disease mouse model were mainly Gb3 isoforms and two Gb3 analogs, such as Gb3(+18) containing the lyso-Gb3(+18) moiety and Gb3(-2) containing the lyso- Gb3(-2) moiety. The total concentrations and Gb3 analog distributions determined by the two methods were comparable. Gb3(+18) levels were high in the kidneys (24% of total Gb3) and the liver (13%), and we observed Gb3(-2) in the heart (10%) and the kidneys (5%). These results indicate organ-specific expression ofGb3analogs, insights that may lead to a deeper understanding of the pathophysiology of Fabry disease.

Influence of Gb3 glycosphingolipids differing in their fatty acid chain on the phase behaviour of solid supported membranes: Chemical syntheses and impact of Shiga toxin binding

The Shiga toxin B subunit (STxB), which is involved in cell membrane attachment and trafficking of Shiga holotoxin, binds specifically to the glycosphingolipid Gb3. In biological membranes, Gb3 glycosphingolipids differ in their fatty acid composition and there is strong evidence that the fatty acid alters the binding behaviour of STxB as well as the intracellular routing of the Shiga toxin/Gb3 complex. To analyse the binding of STxB to different Gb3s, we chemically synthesized saturated, unsaturated, α-hydroxylated Gb3s and a combination thereof, all based on a C24-fatty acid chain starting from monosaccharide building blocks, sphingosine and the respective fatty acids. These chemically well-defined Gb3s were inserted into solid supported phase-separated lipid bilayers composed of DOPC/sphingomyelin/cholesterol as a simple mimetic of the outer leaflet of animal cell membranes. By fluorescence- and atomic force microscopy the phase behaviour of the bilayer as well as the lateral organization of bound STxB were analysed. The fatty acid of Gb 3 significantly alters the ratio between the ordered and disordered phase and induces a third intermediate phase in the presence of unsaturated Gb3. The lateral organization of STxB on the membranes varies significantly. While STxB attached to membranes with Gb3s with saturated fatty acids forms protein clusters, it is more homogeneously bound to membranes containing unsaturated Gb3s. Large interphase lipid redistribution is observed for α-hydroxylated Gb3 doped membranes. Our results clearly demonstrate that the fatty acid of Gb3 strongly influences the lateral organization of STxB on the membrane and impacts the overall membrane organization of phase-separated lipid membranes. the Partner Organisations 2014.

A TOTAL SYNTHESIS OF A STAGE SPECIFIC EMBRYONIC ANTIGEN-3 (SSEA-3), GLOBOPENTAOSYL CERAMIDE, IV3GalGb4Cer. USE OF 2,4,6-TRIMETHYLBENZOYL GROUP AS A STEREOCONTROLLING AUXILIARY

A first total synthesis of a SSEA-3, Galβ1-3GalNAcβ1-3Galα1-4Galβ1-4Glcβ1-3Cer, was achieved in an efficient way by using a key glycopentaosyl glycosyl donor that carried a stereocontrolling auxiliary at O-2a.

Total synthesis of globotriaosyl-E and Z-ceramides and isoglobotriaosyl-E-ceramide.

Stereoselective, total synthesis of O-alpha-D-galactopyranosyl-(1----4) -O-beta-D-galactopyranosyl-(1----4)-O-beta-D-glucopyranosyl-(1----1)-N -tetracosanoyl-[2S,3R,4E (and 4Z)]-sphingenine and O-alpha-D -galactopyranosyl-(1----3)-O-beta-D-galactopyranosyl-(1----4)-O-beta-D -glucopyranosyl-(1----1)-N-tetracosanoyl-(2S,3R,4E)-sphin gen ine was achieved by using O-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl) -(1----4)-O-(2,3,6-tri-O-acetyl-beta-D-galactopyranosyl)-(1----4)-2,3,6- tri-O-acetyl-alpha-D-glucopyranosyl trichloroacetimidate, O-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl) -(1----4)-O-(2,3,6-tri-O-acetyl-beta-D-galactopyranosyl)-(1----4)-2,3,6- tri-O-acetyl-alpha (and beta)-D-glucopyranosyl fluoride, and O-(2,3,4,6-tetra-O-acetyl-alpha-D -galactopyranosyl)-(1----3)-O-(2,3,6-tri-O-acetyl-beta-D-galactopyran osyl)-(1----4)-2,3,6-tri-O-acetyl-alpha-D-glucopyranosyl trichloroacetimidate.