69283-33-6

Usage

Uses

Used in Pharmaceutical Industry:
(2S,3R,4E)-2-hexadecanamido-3-hydroxyoctadec-4-en-1-yl α-galactopyranosyl-(1→4)-β-galactopyranosyl-(1→4)-β-glucopyranoside is used as a pharmaceutical candidate for its potential biological activity and role in cellular processes. Its unique structure and properties make it a promising molecule for the development of new drugs and therapies.
Used in Biochemical Research:
(2S,3R,4E)-2-hexadecanamido-3-hydroxyoctadec-4-en-1-yl α-galactopyranosyl-(1→4)-β-galactopyranosyl-(1→4)-β-glucopyranoside is used as a research tool in biochemistry to study the structure, function, and interactions of complex glycolipids. Its unique structure and potential biological activity make it an interesting molecule for further investigation and understanding of cellular processes.

Upstream product

• 117606-49-2 O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-O-(6-O-benzoyl-2,3-di-O-pivaloyl-β-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-pivaloyl-β-D-glucopyranosyl)-(1->1)-(2S,3R,4E)-2-N-octadecanoylsphingenine 
• 126550-86-5 globotriaosylsphingosine 
• 57-11-4 stearic acid 
• 117603-66-4 tert-butyl ((2S,3R)-1,3-dihydroxypent-4-en-2-yl)carbamate 
• 92052-38-5 2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-lactosyl trichloroacetimidate 
• 112-76-5 Stearoyl chloride 

Relevant academic research and scientific papers

A Diversity-Oriented Strategy for Chemoenzymatic Synthesis of Glycosphingolipids and Related Derivatives

A diversity-oriented strategy combining enzymatic glycan assembly and on-site lipid remodeling via chemoselective cross-metathesis and N-acylation was developed for glycosphingolipid (GSL) synthesis starting from a common, simple glycoside. The strategy was verified with a series of natural GSLs and GSL derivatives and showed several advantages. Most notably, it enabled two-way diversification of the glycan and lipid, including introduction of designed molecular tags, to provide functionalized GSLs useful for biological studies and applications.

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.

'Armed-disarmed' glycosidation strategy based on glycosyl donors and acceptors carrying phosphoroamidate as a leaving group: A convergent synthesis of globotriaosylceramide

A stereocontrolled synthesis of globotriaosylceramide with three different glycosidic linkages has been accomplished by linear and convergent routes exploiting 'armed-disarmed' glycosidation methodology based on glycosyl donors and acceptors carrying tetramethylphosphoroamidate as a leaving group. In particular, the convergent strategy featuring a coupling of a galactosyl(1→4)-galactosyl donor with a glucosylceramide derivative has proven to be extremely efficient.

Total synthesis of globotriaosylceramide (Gb3) and lysoglobotriaosylceramide (lysoGb3)

We have recently reported a highly efficient and stereocontrolled synthesis of globotriaosylceramide (Gb3, 1) in optically pure form.Key to our synthetic strategy was the implementation of the two-stage activation of thioglycosides for formatio