ISSN:
1573-4986
Keywords:
mannoside clusters
;
Concanavalin A
;
pea lectin
;
cross-linking
;
valency
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract Clusters of di-, tri-, and tetra-antennary α-D-mannopyranosides were synthesized in good yields based on the coupling of amine-bearing mono- or trisaccharide {Man α(1→6)[Man α(1→3)]Man} haptens to poly-isocyanate or -isothiocyanate tethering cores. The relative binding properties of the resulting multivalent ligands were determined by turbidimetric and solid phase enzyme-linked lectin assays (ELLA) using plant lectins (phytohemagglutinins) Concanavalin A (Con A) and Pisum sativum (pea lectin) having four and two carbohydrate binding sites, respectively. Rapid and efficient cross-linking between tetravalent Con A and mannopyranosylated clusters were measured by a microtiter plate version of turbidimetric analyses. In inhibition of binding of the lectins to yeast mannan, the best tetravalent monosaccharide (30) and trisaccharide (31) inhibitors were shown to be 140 and 1155 times more potent inhibitors than monomeric methyl α-D-mannopyranoside against pea lectin and Con A, respectively. Compounds 30 and 31 were thus 35 and 289 fold more potent than the reference monosaccharide based on their hapten contents. As a general observation, the ligands bearing the Man α(1→6)[Man α(1→3)]Man trimannoside structures were found to be more potent inhibitors for Con A than the ligands having single mannoside residues, whereas pea lectin could not discriminate between the two types of ligands.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1023/A:1006945028547
Permalink
