Are D-manno-configured Amadori products ligands of the bacterial lectin FimH? (Beilstein Journal of Organic Chemistry)

Abstract The Amadori rearrangement was employed for the synthesis of C-glycosyl-type D-mannoside analogues, namely 1-propargylamino- and 1-phenylamino-1-deoxy-α-D-manno-heptopyranose. They were investigated as ligands of type 1-fimbriated E. coli bacteria by means of molecular docking and bacterial adhesion studies. It turns out that Amadori rearrangement products have a limited activity as inhibitors of bacterial adhesion because the β-C-glycosidically linked aglycone considerably hampers complexation within the carbohydrate binding site of the type 1-fimbrial lectin FimH. Beilstein J. Org. Chem. 2015, 11, 1096–1104. doi:10.3762/bjoc.11.123