Effect ofp-Substitution of Aryl α-D-Mannosides on Inhibiting Mannose-Sensitive Adhesion ofEscherichia coli – Syntheses and Testing

A series of p-substituted aryl α-D-mannosides was synthesized and tested with regard to their inhibitory capacity in the hemagglutination of guinea pig erythrocytes by type 1 fimbriated Escherichia coli. Synthesis of the bivalent, phenyl-linked mannoside cluster 10 was complicated by orthoester formation during the glycosylation reaction. Surprisingly, the inhibitory potency of 10 was lower than that of p-nitrophenyl α-D-mannoside (1) and this is an important finding for the further design of clustered ligands.