528584-66-9

Upstream product

• 67-56-1 methanol 
• 685-73-4 D-galacturonic acid 
• 489-91-8 D-galacturonic acid 
• 83075-41-6 methyl (methyl 2,3,4-tri-O-benzyl-α-D-galactopyranosid)uronate 
• 77-76-9 2,2-dimethoxy-propane 
• 5155-53-3 methyl α-D-galactopyranosiduronic acid 
• 3396-99-4 methyl α-D-galactopyranoside 
• 4356-80-3 methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside 
• 164323-13-1 (2S,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-carboxylic acid 
• 18311-26-7 methyl 6-O-triphenylmethyl-α-D-galactopyranoside 
• 6294-16-2 D-galacturonic acid 
• 616-42-2 dimethylsulfite 
• 124-41-4 sodium methylate 
• 73977-52-3 2,4-di-O-acetyl-β-methyl-D-galactopyranosideuronic acid γ-lactone 

Downstream Products

• 169557-85-1 methyl (methyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate 
• 52678-33-8 1-(methyl ester of 2,3,4-tri-O-benzoyl-β-D-galactopyranuronosyl)uracil 

Relevant academic research and scientific papers

Synthesis and evaluation of glucuronic acid derivatives as alkylating agents for the reversible masking of internucleoside groups of antisense oligonucleotides

2-Iodoethyl (methyl α-D-glucopyranosid)uronate and 2-iodoethyl (methyl β-D-glucopyranosid)thiouronate were prepared in five steps by an efficient synthetic route starting from D-glucuronic acid. Both compounds were used to alkylate dithymidine phosphorothioate and phosphorodithioate diesters, leading to the corresponding phosphotriesters 12 to 15. Hydrolytic stability of 12-15 was studied in different biological media. The enzymatic hydrolysis of 12-15 was accompanied by another reaction resulting in formation of the dithymidine phosphodiesters. Several possible mechanisms for these reactions are proposed.

3'-KETOGLYCOSIDE COMPOUND FOR THE SLOW RELEASE OF A VOLATILE ALCOHOL

The present invention relates to a 3'-ketoglycoside compound defined by formula (I) and its use for controlled release of alcohols, in particular alcohols showing an insect repellent effect. It relates also to a process for preparing the 3'-ketoglycoside compound of formula (I). It further relates to a composition comprising a 3'- ketoglycoside compound of formula (I). It relates also to the use of a 3'-ketoglycoside compound of formula (I) for the controlled release of alcohols. It related also to a method of use of such composition.

Efficient Synthesis of Muramic and Glucuronic Acid Glycodendrimers as Dengue Virus Antagonists

Carbohydrates are involved in many important pathological processes, such as bacterial and viral infections, by means of carbohydrate-protein interactions. Glycoconjugates with multiple carbohydrates are involved in multivalent interactions, thus increasing their binding strengths to proteins. In this work, we report the efficient synthesis of novel muramic and glucuronic acid glycodendrimers as potential Dengue virus antagonists. Aromatic scaffolds functionalized with a terminal ethynyl groups were coupled to muramic and glucuronic acid azides by click chemistry through optimized synthetic strategies to afford the desired glycodendrimers with high yields. Surface Plasmon Resonance studies have demonstrated that the compounds reported bind efficiently to the Dengue virus envelope protein. Molecular modelling studies were carried out to simulate and explain the binding observed. These studies confirm that efficient chemical synthesis of glycodendrimers can be brought about easily offering a versatile strategy to find new active compounds against Dengue virus.

A Potent Mimetic of the Siglec-8 Ligand 6’-Sulfo-Sialyl Lewisx

Siglecs are members of the immunoglobulin gene family containing sialic acid binding N-terminal domains. Among them, Siglec-8 is expressed on various cell types of the immune system such as eosinophils, mast cells and weakly on basophils. Cross-linking of Siglec-8 with monoclonal antibodies triggers apoptosis in eosinophils and inhibits degranulation of mast cells, making Siglec-8 a promising target for the treatment of eosinophil- and mast cell-associated diseases such as asthma. The tetrasaccharide 6’-sulfo-sialyl Lewisx has been identified as a specific Siglec-8 ligand in glycan array screening. Here, we describe an extended study enlightening the pharmacophores of 6’-sulfo-sialyl Lewisx and the successful development of a high-affinity mimetic. Retaining the neuraminic acid core, the introduction of a carbocyclic mimetic of the Gal moiety and a sulfonamide substituent in the 9-position gave a 20-fold improved binding affinity. Finally, the residence time, which usually is the Achilles tendon of carbohydrate/lectin interactions, could be improved.

Synthesis, characterization, and crystal structure of sodium (methyl α- D -mannopyranosid)uronate monohydrate

TEMPO (2,2,6,6-tetramethylpiperidine-1-oxyl)-mediated oxidation of methyl α-d-mannopyranoside with sodium hypochlorite gave sodium (methyl α-d-mannopyranosid)uronate, which was obtained as a crystalline monohydrate in ~70% yield without chromatography. Its purity was proved by NMR spectroscopy, a newly developed HPLC method, combustion analysis, and X-ray crystallography. The crystal structure, solved from synchrotron diffraction data in space group P212121, revealed that the packing of the uronate molecules is connected by an extensive network of hydrogen bonds, and that the Na+ ion is coordinated by six oxygen ligands from one water and three surrounding sugar molecules. Georg Thieme Verlag Stuttgart New York.

Enantioselective de novo synthesis of 4-deoxy-d-hexopyranoses via hetero-Diels-Alder cycloadditions: Total synthesis of ezoaminuroic acid and neosidomycin

The de novo synthesis of carbohydrates constitutes an important aspect of organic chemistry, and its application toward deoxy sugars is particularly noteworthy in targeting biologically active compounds. The enantioselective preparation of 4-deoxy-d-ribo-, 4-deoxy-d-lyxo-, and 4-deoxy-d-xylo- hexopyranosides, along with their uronate counterparts has been successfully accomplished using hetero-Diels - Alder reactions as the key step. Jacobsen chromium(III) catalyst and a titanium - binaphthol complex have been used to successfully catalyze diene and aldehyde cycloadditions, leading to optically active dihydropyran templates. 6-Hydroxydesosamine, orthogonally protected ezoaminuroic acid, and neosidomycin were synthesized using a comparative study. Also, a novel chiron approach to 4-deoxy-lyxo-hexopyranosiduronic acid methyl ester derivatives was efficiently accomplished starting from readily accessible starting materials. This work represents a systematic and comprehensive study toward a de novo synthesis of 4-deoxy-hexopyranoses via enantioselective hetero-Diels-Alder reactions.

Glycoside cleavage by a new mechanism in unsaturated glucuronyl hydrolases

Unsaturated glucuronyl hydrolases (UGLs) from GH family 88 of the CAZy classification system cleave a terminal unsaturated sugar from the oligosaccharide products released by extracellular bacterial polysaccharide lyases. This pathway, which is involved in extracellular bacterial infection, has no equivalent in mammals. A novel mechanism for UGL has previously been proposed in which the enzyme catalyzes hydration of a vinyl ether group in the substrate, with subsequent rearrangements resulting in glycosidic bond cleavage. However, clear evidence for this mechanism has been lacking. In this study, analysis of the products of UGL-catalyzed reactions in water, deuterium oxide, and dilute methanol in water, in conjunction with the demonstration that UGL rapidly cleaves thioglycosides and glycosides of inverted anomeric configuration (substrates that are resistant to hydrolysis by classical glycosidases), provides strong support for this new mechanism. A hydration-initiated process is further supported by the observed UGL-catalyzed hydration of a C-glycoside substrate analogue. Finally, the observation of a small β-secondary kinetic isotope effect suggests a transition state with oxocarbenium ion character, in which the hydrogen at carbon 4 adopts an axial geometry. Taken together, these observations validate the novel vinyl ether hydration mechanism and are inconsistent with either inverting or retaining direct hydrolase mechanisms at carbon 1.

Synthesis of apiose-containing oligosaccharide fragments of the plant cell wall: Fragments of rhamnogalacturonan-II side chains A and B, and apiogalacturonan

Fragments of pectic polysaccharides rhamnogalacturonan-II (RG-II) and apiogalacturonan were synthesised using p-tolylthio apiofuranoside derivatives as key building blocks. Apiofuranose thioglycosides can be conveniently prepared by cyclization of the cor

Antioxidant and semicarbazide-sensitive amine oxidase inhibitory activities of glucuronic acid hydroxamate

The antioxidant and inhibitory activities of glucuronic acid (GluA) and its synthesized 1-methoxyl-6-glucuronic acid hydroxamate (GluA-NHOH) against semicarbazide-sensitive amine oxidase (SSAO) were investigated. The scavenging activities of GluA-NHOH aga

Electroorganic synthesis in oil-in-water (O/W) nanoemulsion: TEMPO-mediated electrooxidation of amphiphilic alcohols in water

Oil-in-water nanoemulsion which consisted of TEMPO, amphiphilic alcohols, and water offered unique reaction environments for electrooxidation of the alcohols to give the corresponding carboxylic acids in good to excellent yields.