78679-14-8

Upstream product

• 100-02-7 4-nitro-phenol 
• 14227-90-8 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide 
• 1195182-65-0 (4-nitro-phenyl)-(tri-O-acetyl-β-D-arabinopyranoside) 

Downstream Products

• 1089715-92-3 p-amidophenyl-α-L-arabinopyranoside 
• 100-02-7 4-nitro-phenol 
• 1195553-62-8 (4-amino-phenyl)-β-D-arabinopyranoside 
• 643758-65-0 p-Nitrophenyl 2,3-di-O-benzoyl-α-L-arabinopyranoside 

Relevant academic research and scientific papers

Carbohydrate-carbohydrate interactions in water with glycophanes as model systems

The synthesis and conformational properties of glycophanes 2 and 3 (cyclodextrin-cyclophane hybrid receptors containing two maltose units linked by (4-hydroxymethyl) benzoic acid spacer) are described. The binding properties in water of these receptors with a series of 4-nitrophenyl glycosides with α- and β-configurations at the anomeric center have been studied using 1H NMR spectroscopy and molecular mechanics calculations. A comparison of these properties with those of glycophane 1 (an α,α-trehalose containing glycophane) and α-cyclodextrin (αCD) using the same glycosides shows the existence of a stabilizing contribution to the free energy of binding in the case of of glycophanes but not in the case of the αCD system. This contribution is due to carbohydrate-carbohydrate interactions between both host and guest lipophilic sugar surfaces. Glycophanes 1, 2, and 3 show similar α/β selectivity on binding the ligands, despite the great flexibility of 3 related to 1 and 2. Parallels are drawn between the thermodynamic behavior of these model systems and that proposed for sugar- protein interactions.