7073-61-2

Upstream product

• 6907-84-2 (3β)-cholest-5-en-3-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 81058-30-2 (5-Cholesten-3β-yl)-2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosid 
• 57-88-5 cholesterol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 149707-75-5 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate 
• 4196-35-4 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 1012046-44-4 benzoxazolyl 2,3,4-tri-O-benzoyl-6-O-(3-hydroxycarbonylpropanoyl)-β-D-glucopyranoside 
• 149707-76-6 O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl) trichloroacetimidate 
• 66252-72-0 (5-Cholesten-3β-yl)-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosid 

Relevant academic research and scientific papers

Synthesis and delivery activity of new cationic cholesteryl glucosides

Cholesterol amphiphiles containing positively charged groups (pyridinium, N-methylimidazolium, N-methylmorpholinium, and N-methylpiperidinium) linked via β-glucosyl spacer were prepared by alkylation of the corresponding bases with 6 - mesyl-β-d-cholesteryl glucopyranoside. IC50 values were in the range 20-35 μM for the series of compounds and liposomal formulations with DOPE (1:1) were significantly less toxic. The liposomal formulations provided the accumulation of FITC-labeled oligonucleotide in cells, and the efficiency of this process was comparable to that of Lipofectamine 2000. Cationic liposomes were able to deliver siRNA into the cells, and the liposomal formulation 7d/DOPE provided the most pronounced down-regulation of EGFP expression both in the presence and in the absence of serum (up to 30%).

Analysis of steryl glucosides in rice bran-based fermented food by LC/ESI-MS/MS

Steryl glucosides (SGs) and acylated steryl glucosides (ASGs) are phytochemicals found in plant-based foods and are known as bioactive compounds with potential health benefits. These include anti-inflammatory properties, anti-diabetic effects, and modulation of immunoregulatory functions as well as having cholesterol lowering effects. In this study, three major SGs, i.e., glucosides of β-sitosterol, stigmasterol, and campesterol, were synthesized and used as standards for measurement of their contents in rice bran (RB)-based fermented food (FBRA) utilizing Aspergillus oryzae and raw material (RM). The compounds were quantified using liquid chromatography/electrospray ionization-tandem mass spectrometry. It was found that β-sitosteryl glucoside was most abundant among the analyzed glucosides in both samples, and the contents of each SG in FBRA decreased about 35% from those of RM. In contrast to SGs, the contents of ASGs in FBRA increased 1.5-fold during the fermentation process as evidenced by an alkaline hydrolysis. The present results suggest that the FBRA might have greater beneficial effects than the RM, since ASGs have shown to have more potent cholesterol lowering effects and stronger anti-diabetic properties than SGs.

Characterization and Quantitation of Steryl Glycosides in Solanum melongena

Glycosylated plant sterols or steryl glycosides (SGs) are a small group of glycolipids occurring ubiquitously in plants. In contrast to free sterols, they are insufficiently characterized concerning structural variety, quantity, and biological function. I

Tandem glycosyl iodide glycosylation and regioselective enzymatic acylation affords 6-o-tetradecanoyl-α- d -cholesterylglycosides

A generalized synthesis of α-d-cholesterylglycosides has been achieved using one-pot per-O-trimethylsilyl glycosyl iodide glycosidation. Both cholesteryl α-d-glucopyranoside (αCG) and cholesteryl α-d-galactopyranoside were prepared in high yield. These compounds were further esterified using regioselective enzymatic acylation with tetradecanoyl vinyl ester to afford 6-O-tetradecanoyl-α-d-cholesteryl glucopyranoside (αCAG) of Helicobacter pylori and the corresponding galactose analogue in 66-78% overall yields from free sugars. The tandem step-economy sequence provides novel analogues to facilitate glycolipidomic profiling.

Cholesteryl glucosides signal through the carbohydrate recognition domain of the macrophage inducible C-type lectin (mincle)

Cholesteryl α-d-glucosides (αGCs) are unique metabolic products of the cancer-causing human pathogenHelicobacter pylori.Viasignalling through the Macrophage inducible C-type lectin (Mincle) and the induction of a pro-inflammatory response, they are thought to play a role in the development of gastric atrophy. Herein, we prepared the first library of steryld-glucosides and determined that they preferentially signal through the carbohydrate recognition domain of human Mincle, rather than the amino acid consensus motif. Lipidated steryld-glucosides exhibited enhanced Mincle agonist activity, with C18 cholesteryl 6-O-acyl-α-d-glucoside (2c) being the most potent activator of human monocytes. Despite exhibiting strong Mincle signalling, sito- (5b) and stigmasterol glycosides (6b) led to a poor inflammatory response in primary cells, suggesting that Mincle is a potential therapeutic target for preventingH. pylori-mediated inflammation and cancer.

Novel steroid -based amphiphiles and uses thereof

The present invention relates to a newly developed steroid-based amphiphilic compound, a preparation method thereof and a method for extracting, solubilizing, stabilizing, crystallizing or analyzing membrane proteins using the same. In addition, the compound, compared to the conventional compounds, can efficiently extract membrane proteins having various structures and properties from cell membranes and store the same in an aqueous solution for a long time, and thus can be used for functional analysis and structural analysis. Membrane protein structure and function analysis thereof is one of the areas of greatest interest in current biology and chemistry by being closely related to drug development.COPYRIGHT KIPO 2020

Direct glycosylation of bioactive small molecules with glycosyl iodide and strained olefin as acid scavenger

A new strategy for diversity-oriented direct glycosylation of bioactive small molecules was developed. This reaction features (-)-β-pinene as acid scavenger and work with glycosyl iodides under mild conditions. With the aid of RP-HPLC and chiral SFC separation techniques, the new direct glycosylation proved effective at gram scale on bioactive small molecules including AZD6244, podophyllotoxin, paclitaxel, and docetaxel. Interesting glycoside derivatives were efficiently created with good yields and 1,2-cis selectivity.

HAIR GROWTH AND HAIR RESTORATION MATERIAL

Provided is a novel hair growth and hair restoration material having excellent efficacy in hair growth and hair restoration for both men and women, even when the components thereof are at ultra-dilute concentrations; the hair growth and hair restoration material being characterized in containing a steryl glucopyranoside, preferably a cholesteryl glucopyranoside, represented by general formula (I). (In the formula, Z represents a sterol residue from which the hydroxyl group attached to the 3-position of a cyclopentanohydrophenanthrene ring has been removed.)

Application of glycosyl thioimidates in solid-phase oligosaccharide synthesis

(Chemical Equation Presented) Two stable classes of thioimidoyl derivatives, S-benzoxazolyl (SBox) and S-thiazolinyl (STaz) glycosides, were investigated as glycosyl donors for solid-phase oligosaccharide synthesis. It was demonstrated that these derivatives are suitable for both glycosyl acceptor-bound and glycosyl donor-bound strategies, commonly employed in resin-supported oligosaccharide synthesis.

High-Yield Syntheses of Tetra-O-benzyl-α-D-glucopyranosyl bromide and Tetra-O-pivaloyl-α-D-glucopyranosyl bromide and their Advantage in the Koenigs-Knorr Reaction

Several improved approaches for the preparation of tetra-O-benzyl-α- D-glucopyranosyl bromide and tetra-O-pivaloyl-α-D-glucopyranosyl bromide are discussed. The importance of these compounds, which are useful glycosyl donors, was demonstrated by successful preparation of cholesteryl glucopyranosides in an almost neutral medium without the formation of orthoesters. In addition, accurate 1H and 13C NMR resonance assignments of the synthesized cholesteryl glycosides were performed by 2D NMR spectroscopy. Springer-Verlag 2006.