Studies of the molecular recognition of synthetic methyl β-lactoside analogues by Ricinus communis agglutinin

Specificities ofRicinus communisagglutinin 120 interaction with sulfated galactose

“…The binding properties of RCA 120 and ECL to different oligosaccharides have been investigated extensively by using immune-precipitation [12], inhibition [4,5,31], affinity chromatography [2], NMR spectroscopy [32], isothermal titration calorimetry and surface plasmon resonance method [33] with emphasis on the Galb1-containing neutral oligosaccharides. Direct binding assays using various immobilized oligosaccharide probes in an array format have found increasing use in deriving directly the specificities of carbohydrate binding proteins [3,19,21,[27][28][29].…”

Synthesis of deoxy and acylamino derivatives of lactose and use of these for probing the active site of Neisseria meningitidis N-acetylglucosaminyltransferase

“…4,5 In the case of 12, 16 and 24, the 3 0 , 4 0 and 2 0 hydroxy functions, respectively, were removed by tributyltin-mediated radical reduction of thiocarbonyl derivatives. In the case of compound 6, the 6 0 -hydroxy function was removed by NBS-opening 6 of a benzylidene compound followed by catalytic hydrogenation.…”

Analysis of Protein–Carbohydrate Interaction Using Engineered Ligands

“…For instance, the PGal-( 1 -4/3)-GlcNAc-specific lectins isolated from Ricinus communis seeds (ricin and R. communis agglutinin) and from bovine heart (galectin-1) display differences in the recognition of naturally occurring oligosaccharides based on this backbone sequence, such as the preferential binding of both ricin and agglutinin to aNeuAc-(2-6)-substituted rather than a-(2-3)-substituted P-galactoside-terminating oligosaccharides, as opposed to the different preference of bovine lectin. Studies on the molecular recognition of different synthetic monodeoxy, fluorodeoxy, 0-methyl and other derivatives of methyl P-lactoside by these three lectins (Rivera-Sagredo et al, 1991, 1992bSolis et al, 1993Solis et al, , 1994bFernandez et al, 1994) al., 1994), the preferred conformations of the different methyl P-lactoside derivatives were very similar. Therefore, the relative affinity of the lectins for the different structures could be correlated with specific polar and nonpolar interactions.…”

“…Therefore, the relative affinity of the lectins for the different structures could be correlated with specific polar and nonpolar interactions. Analysis of the results indicated that the hydroxyl groups at positions 3, 4 and 6 of the galactopyranose unit are key polar groups in the interaction with both rich and R. communis agglutinin (Rivera-Sagredo et al, 1991, 1992bSolis et al, 1993). HO-2' also participates in hydrogen bonding to both lectins and, at the glucopyranose unit, the hydroxyl group at position 6 participates in a minor polar interaction with ricin but not with the agglutinin.…”

“…HO-2' also participates in hydrogen bonding to both lectins and, at the glucopyranose unit, the hydroxyl group at position 6 participates in a minor polar interaction with ricin but not with the agglutinin. In addition, a nonpolar interaction involving position 3 of the glucopyranose moiety plays a significant role in the binding to both lectins (Rivera-Sagredo et al , 1992b;Fernhdez et al, 1994).…”