10357-03-6

Upstream product

• 1824-94-8 methyl beta-D-galactopyranoside 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 67-56-1 methanol 
• 643-33-4 D-galacturonic acid 
• 4356-82-5 (2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid 
• 62435-44-3 methyl (methyl 2,3,4-tri-O-benzyl-β-D-galactopyranosid)uronate 
• 40653-32-5 methyl 2,3,4-tri-O-benzyl-β-D-galactopyranoside 
• 18311-26-7 methyl 6-O-triphenylmethyl-β-D-galactopyranoside 
• 5241-02-1 O¹-methyl-β-D-galactopyranuronic acid 
• 124-41-4 sodium methylate 
• 73977-52-3 2,4-di-O-acetyl-β-methyl-D-galactopyranosideuronic acid γ-lactone 
• 685-73-4 D-galacturonic acid 
• 616-42-2 dimethylsulfite 

Relevant academic research and scientific papers

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 OF METHYL ETHERS OF METHYL (METHYL β-D-GALACTOPYRANOSID) URONATE

The oxidation of methyl β-D-galactopyranoside with oxygen in the presence of platinum and carbon gave methyl (methyl β-D-galactopyranosid)uronate, (I) with a yield of 20percent.The partial methylation of (I) with methyl iodide in the presence of silver ox

METHANOLYSIS STUDIES OF CARBOHYDRATES, USING H.P.L.C.

An h.p.l.c. system that separates carbohydrates as their methyl glycosides has been used to study the products obtained on treatment of various carbohydrates with methanolic hydrogen chloride.Results are presented for the monosaccharide composition of several polysaccharides, lactone and ester formation during the treatment of D-glucuronic acid, and relative rates of glycosidation vs. esterification during the treatment of D-galacturonic acid.

PROTON AND CARBON-13 NUCLEAR MAGNETIC RESONANCE STUDIES ON METHYL (METHYL D-GALACTOSID)URONATES AND THEIR PER-O-ACETYL DERIVATIVES

The 1H- and 13C-n.m.r. spectra of the anomeric methyl (methyl D-galactosid)uronates, as well as the 1H-n.m.r. spectra of their acetyl derivatives, were analyzed.The spectra of the unacetylated D-galactopyranosiduronates showed good correlation with those of the corresponding anomeric D-galactopyranuronic acids and their methyl esters, and with those of the anomeric methyl D-galactopyranosides.From the values of the chemical shifts and coupling constants, it was concluded that the anomeric methyl (methyl D-galactopyranosid)uronates and their corrasponding peracetates are in the 4C1(D) conformation.The chemical shifts in the 13C-n.m.r. spectra show good correlation with those of the methyl D-galactosides.The signals of the furanose derivatives appear at fields lower than those of the corresponding pyranose compounds.