345320-72-1

Upstream product

• 345320-68-5 Methyl 4-O-(4,6-O-benzylidene-β-D-galactopyranosyl)-6-O-(tert-butyldimethylsilyl)-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 137119-40-5 methyl 4-O-(4,6-O-benzylidene-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 345320-70-9 Methyl 2,3-di-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl)-6-O-(tert-butyldimethylsilyl)-β-D-glucopyranoside 

Downstream Products

• 345320-77-6 Methyl 2,3-di-O-benzyl-4-O-(2,3-di-O-benzyl-6-O-benzoyl-β-D-galactopyranosyl)-6-O-methoxycarbonylmethyl-β-D-glucopyranoside 
• 345320-75-4 Methyl 2,3-di-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl)-6-O-methoxycarbonylmethyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

Carbohydrate-carbohydrate recognition between Lewis X blood group antigens, mediated by calcium ions

Bivalent Lewis X (LeX) oligosaccharides were synthesised in order to study the conformational details of carbohydrate clusters by NMR spectroscopy. To this end, two Lex trisaccharide moieties (1) were covalently linked through the 6-hydroxy group or through the anomeric oxygen of GlcNAc to yield dimers 2 and 3, respectively. The two Lex halves of the model saccharide 2 exhibited cooperativity in calcium binding. Three different lactosides served as control compounds for NMR titration with calcium chloride. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Synthesis and structure-activity relationships of di- and trisaccharide inhibitors for Shiga-like toxin Type 1

The syntheses of galabiose and Pk-trisaccharide analogues in which selected hydroxy groups are replaced by O-methyl, amino deoxy, acetamido deoxy, and carboxyalkyl groups are reported. The ability of these inhibitors to block E. coli verotoxin 1 binding to its mammalian cell-surface receptor are evaluated by a solid-phase competition assay. The synthesis of a biotinylated glycoconjugate for this assay is described, wherein a Pk-trisaccharide tether derivative 70 is constructed and covalently attached to bovine serum albumin followed by biotinylation. Galabiose derivatives 4 and 5 that contain a carboxymethyl or carboxyethyl substituent at O-2 of the β-galactose residue show 15-20-fold activity gains over the methyl glycoside of galabiose. This enhanced activity is not observed for the corresponding carboxymethyl-substituted Pk-trisaccharide analogue 13. The inhibition data are rationalized with the solved crystal structure for verotoxin 1 complexed with a Pk-trisaccharide analogue and provide insight for the design of dimeric inhibitors that can exploit the unique binding-site distribution of the toxin's B subunit. This discussion provides a further example of the important role played by ordered water molecules in sugar-protein complexes.