61198-76-3

Upstream product

• 16977-77-8 (2-chloroethyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 107-07-3 2-chloro-ethanol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 18607-66-4 2-chloroethyl D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 4163-60-4 β-D-galactose peracetate 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 50-99-7 D-glucose 

Downstream Products

• 139888-80-5 2-azidoethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 

Relevant academic research and scientific papers

Synthesis and Characterization of Novel Fluoro-glycosylated Porphyrins that can be Utilized as Theranostic Agents

Small molecules with modalities for a variety of imaging techniques as well as therapeutic activity are essential, as such molecules render opportunities to simultaneously conduct diagnosis and targeted therapy, so called theranostics. In this regard, gly

GLYCOMIMETIC COMPOUNDS AS ANTI-INFECTIOUS AGAINST PATHOGENS LECTINS

The present invention relates to a calixarene-based glycosylated compound (I) having the formula: (I) wherein D is independently selected in the group comprising a —CH2-group, an oxygen atom, a sulphur atom, a sulfinyl group or a sulfonyl group, E is independently selected in the group comprising a hydrogen, an alkyl having from 1 to 10 carbon atoms, an aryl having from 6 to 20 carbon atoms, a nitrogen dioxide group, an azide group, an amino group, a guanidinium group, a halogen atom, a —CH2R group wherein R is a hydroxyl, a halogen, an amino group, a N(alkyl)2 group, a NH(alkyl) group, or E represents a —CO—R′ wherein R′ is a hydrogen atom, a hydroxyl group or an amino, B represents a A-C group wherein A is independently selected in the group comprising an oxygen atom, a sulfur atom, a NH group or a (CH2)i group, i being an integer from 1 to 10, C is independently selected in the group comprising a hydrogen, an alkyl, an alkenyl, an alkynyl, or C is a group of formula (II). The present invention also relates to a pharmaceutical composition characterized in that it comprises the said calixarene-based glycosylated compound (I), in combination with pharmaceutically acceptable carriers or diluents. The present invention also relates to the use of the said calixarene-based glycosylated compound (I) or the said pharmaceutical composition, for the manufacture of a drug intended to prevent or treat bacterial infections from pathogens that use lectins in the first steps of infection.

GLYCOMIMETIC COMPOUNDS AS ANTI-INFECTIOUS AGAINST PATHOGENS LECTINS

The present invention relates to a calixarene-based glycosylated compound (I) having the formula : (I) wherein D is independently selected in the group comprising a –CH2 –group, an oxygen atom, a sulphur atom, a sulfinyl group or a sulfonyl group, E is independently selected in the group comprising a hydrogen, an alkyl having from 1 to 10 carbon atoms, an aryl having from 6 to 20 carbon atoms, a nitrogen dioxide group, an azide group, an amino group, a guanidinium group,a halogen atom, a –CH2 R group wherein R is a hydroxyl, a halogen, an amino group, a N(alkyl)2 group, a NH(alkyl) group, or E represents a –CO-R' wherein R' is a hydrogen atom, a hydroxyl group or an amino, B represents a A–C group wherein A is independently selected in the group comprising an oxygen atom, a sulfur atom, a NH group or a (CH2 )i group, i being an integer from 1 to 10, C is independently selected in the group comprising a hydrogen, an alkyl, an alkenyl, an alkynyl, or C is a group of formula (II). The present invention also relates to a pharmaceutical composition characterized in that it comprises the said calixarene-based glycosylated compound (I), in combination with pharmaceutically acceptable carriers or diluents. The present invention also relates to the use of the said calixarene-based glycosylated compound (I) or the said pharmaceutical composition, for the manufacture of a drug intended to prevent or treat bacterial infections from pathogens that use lectins in the first steps of infection.

Rational design and synthesis of optimized glycoclusters for multivalent lectin-carbohydrate interactions: Influence of the linker arm

The design of multivalent glycoclusters requires the conjugation of biologically relevant carbohydrate epitopes functionalized with linker arms to multivalent core scaffolds. The multigram-scale syntheses of three structurally modified triethyleneglycol analogues that incorporate amide moiety(ies) and/or a phenyl ring offer convenient access to a series of carbohydrate probes with different water solubilities and rigidities. Evaluation of flexibility and determination of preferred conformations were performed by conformational analysis. Conjugation of the azido-functionalized carbohydrates with tetra-propargylated core scaffolds afforded a library of 18 tetravalent glycoclusters, in high yields, by CuI-catalyzed azide-alkyne cycloaddition (CuAAC). The compounds were evaluated for their ability to bind to PA-IL (the LecA lectin from the opportunistic pathogen Pseudomonas aeruginosa). Biochemical evaluation through inhibition of hemagglutination assays (HIA), enzyme-linked lectin assays (ELLA), surface plasmon resonance (SPR), and isothermal titration microcalorimetry (ITC) revealed improved and unprecedented affinities for one of the monovalent probes (Kd=5.8 μM) and also for a number of the tetravalent compounds that provide several new nanomolar ligands for this tetrameric lectin. Copyright

Efficient glycosylation of unprotected sugars using sulfamic acid: A mild eco-friendly catalyst

Sulfamic acid, a mild and environmentally benign catalyst has been successfully used in the Fischer glycosylation of unprotected sugars for the preparation alkyl glycosides. A diverse range of aliphatic alcohols have been used to prepare a series of alkyl glycosides in good to excellent yield.

Variations on the SnCl4 and CF3CO2Ag-promoted glycosidation of sugar acetates: a direct, versatile and apparently simple method with either α or β stereocontrol

Glycosidation of sugar peracetates (d-gluco, d-galacto) with SnCl4 and CF3CO2Ag led to either 1,2-cis-, or 1,2-trans-glycosides, depending primarily on the alcohols used. In particular, 1,2-trans-glycosides, expected from acyl-protected glycosyl donors, were formed in high yields with alcohols sharing specific features such as bulkiness, presence of electron-withdrawing groups or polyethoxy motifs. In contrast, simple alcohols afforded ～1:1 mixtures of 2,3,4,6-tetra-O-acetyl, and 3,4,6-tri-O-acetyl 1,2-cis-glycosides due to anomerization and/or acid-catalyzed fragmentation of 1,2-orthoester intermediates. After reacetylation or deacetylation, acetylated or fully deprotected 1,2-cis-glycosides (α-d-gluco, α-d-galacto) were obtained in ～90% yields by a simple and direct method.

Discovery of the chemical function of glycosidases: Design, synthesis, and evaluation of mass-differentiated carbohydrate libraries

Equation presented. Discovery of the catalytic chemical function of the many putative glycosidases coded in genomes currently relies on individual testing of possible substrates, usually as their p-nitrophenol conjugate. Herein, we present an alternative chemical proteomics approach using a synthetic mass-differentiated heat-stable substrate library with mass spectrometry readout. Library components do not serve as reaction inhibitors and both primary and secondary enzyme substrates can be delineated.

Studies on Koenigs-Knorr Glycosidations

Mercury salt and silver triflate-promoted Koenigs-Knorr reactions of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide and 2-O-benzoyl-3,4,6-tri-O-acetyl-α-D-glucopyranosyl bromide with mono, di and trichloroethanol were studied.The products in each react