23661-33-8

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 7432-72-6 methyl 2,3,4-tri-O-acetyl-α-D-glucopyranose 
• 108-24-7 acetic anhydride 
• 6619-09-6 methyl 6-O-tosyl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 

Downstream Products

• 6619-09-6 methyl 6-O-tosyl-α-D-glucopyranoside 
• 21893-05-0 methyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-β-L-idopyranoside 
• 20113-43-3 1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-α-D-glucopyranose 
• 23701-87-3 methyl 6-azido-6-deoxy-α-D-glucopyranoside 
• 5155-47-5 methyl 6-amino-6-deoxy-α-D-glucopyranoside 
• 17184-28-0 Methyl-3,6-anhydro-α-D-glucofuranosid 
• 59202-80-1 Acetic acid (2R,3R,4S,5R)-4,5-diacetoxy-6-bromo-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 69240-09-1 2,3,4-tri-O-acetyl-1,5-anhydro-6-O-(4-methylphenylsulfonyl)-D-arabino-hex-1-enitol 
• 871011-08-4 2,3,4-tri-O-acetyl-1-S-methylsulfonyl-6-O-(4-methylphenylsulfonyl)-1-thio-β-D-glucose 
• 871010-58-1 2,3,4-tri-O-acetyl-6-S-acetyl-S-phenylsulfonyl-1,6-dithio-β-D-glucose 

Relevant academic research and scientific papers

AMYLOID TARGETING AGENTS AND METHODS OF USING THE SAME

Provided herein is the design and synthesis of novel molecular rotor fluorophores useful for detection of amyloid or amyloid like proteins. The fluorophores are designed to exhibit enhanced fluorescence emission upon associating with amyloid or amyloid like proteins as compared to unbound compound. Also disclosed herein are the methods for treating of diseases associated with an amyloid or amyloid like proteins.

Synthesis and Evaluation of the Biological Profile of Novel Analogues of Nucleosides and of Potential Mimetics of Sugar Phosphates and Nucleotides

The synthesis of purine/triazole 6'-isonucleosides and of glucuronic acid/glucuronamide-derived N-glycosylsulfonohydrazides through efficient and stereo- or regioselective methodologies is described. Their structures were envisaged to mimic nucleosides, s

Phosphatidylinositol 3-phosphate mimics based on a sulfoquinovose scaffold: Synthesis and evaluation as protein kinase B inhibitors

New sulfoquinovose analogues of phosphatidylinositol 3-phosphate have been synthesised based on a sulfoquinovose scaffold as potential protein kinase B (PKB) inhibitors. The synthetic strategy involved the introduction into glucose of a thioacetate group at the 6-position and of an azide group at the anomeric position as precursors of the sulfonate and phosphoramidate moieties present in the final compounds. The synthesised compounds were tested in vitro on isolated PKB by means of ELISA assays and for their anti-proliferative activity against the human ovarian carcinoma cell line IGROV-1. Sulfoquinovose derivatives 2b and 2c showed inhibitory activity in the low micromolar range.

Quantifying the electronic effects of carbohydrate hydroxy groups by using aminosugar models

Methyl amino-deoxy-glycosides with α- and β-gluco, α-galacto, or α-manno stereochemistry with the amino functionality in each of the four possible non-anomeric positions have been synthesized and their pKa values determined by titration. These

Development and characterization of lysine based tripeptide analogues as inhibitors of Sir2 activity

Sirtuins are NAD+ dependent deacetylases that modulate various essential cellular functions. Development of peptide based inhibitors of Sir2s would prove useful both as pharmaceutical agents and as effectors by which downstream cellular alterations can be monitored. Click chemistry that utilizes Huisgen's 1,3-dipolar cycloaddition permits attachment of novel modifications onto the side chain of lysine. Herein, we report the synthesis of peptide analogues prepared using click reactions on Nε-propargyloxycarbonyl protected lysine residues and their characterization as inhibitors of Plasmodium falciparum Sir2 activity. The peptide based inhibitors exhibited parabolic competitive inhibition with respect to acetylated-peptide substrate and parabolic non-competitive inhibition with NAD+ supporting the formation of EI2 and E·NAD+·I2 complexes. Cross-competition inhibition analysis with the non-competitive inhibitor nicotinamide (NAM) ruled out the possibility of the NAM-binding site being the second inhibitor binding site, suggesting the presence of a unique alternate pocket accommodating the inhibitor. One of these compounds was also found to be a potent inhibitor of the intraerythrocytic growth of P. falciparum with 50% inhibitory concentration in the micromolar range.

Analogues of moranoline and MDL 73945. Methyl 6(5)-deoxy-6(5)-(morpholin-4-yl)α-D-glycosides as glucosidase inhibitors

Methyl 2,3,4-tri-O-acetyl-6-O-(p-tolylsulfonyl)-α-D-glucopyranoside (6), or its iodo analogue 7, were subjected to nucleophilic displacement with morpholine to give 8, deacetylation of which gave methyl 6-deoxy-6-(morpholin-4-yl)-α-D-glucopyranoside (3). Similarly, 11, 12 and 21 were prepared. The 6-deoxy-6-iodo derivative 16 was subjected to nucleophilic displacement with morpholine and subsequent acetylation to give 15. Deacetylation of 15 gave 17. The kinetic studies for the inhibition of β-D-glucosidase from sweet almond and using o-nitrophenyl β-D-glucopyranoside as substrate exhibited a Ki value for 21 on the same order as 1-deoxynojirimycin whereas for 3, a Ki value of lesser order was observed.

Use of Ferric Chloride in Carbohydrate Reactions: Part V - Acetolysis of Methyl Hexopyranosides Using Ferric Chloride in Acetic Anhydride

Treatment of methyl α-D-gluco- and galacto-pyranosides with acetic anhydride-ferric chloride reagent results in the acetolysis of the glycosides.Anomeric mixtures of the sugar peracetates in their pyranose and furanose forms and acyclic peracetates are obtained.The rate of acetolysis is retarded by the introduction of a tosyl function at position-6.