title: Are D-manno-configured Amadori products ligands of the bacterial lectin FimH?
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.
authors.affiliation: Christiana Albertina University of Kiel, Otto Diels Institute of Organic Chemistry, Otto-Hahn-Platz 3/4, D-24118 Kiel, Germany,.
authors.forename: Tobias-Elias
authors.initials: TE
authors.lastname: Gloe
authors.affiliation: Christiana Albertina University of Kiel, Otto Diels Institute of Organic Chemistry, Otto-Hahn-Platz 3/4, D-24118 Kiel, Germany,.
authors.forename: Insa
authors.initials: I
authors.lastname: Stamer
authors.affiliation: Glycogroup, Institute of Organic Chemistry, Technical University Graz, Stremayrgasse 9, A-8010 Graz, Austria.
authors.forename: Cornelia
authors.initials: C
authors.lastname: Hojnik
authors.affiliation: Glycogroup, Institute of Organic Chemistry, Technical University Graz, Stremayrgasse 9, A-8010 Graz, Austria.
authors.forename: Tanja M
authors.initials: TM
authors.lastname: Wrodnigg
authors.affiliation: Christiana Albertina University of Kiel, Otto Diels Institute of Organic Chemistry, Otto-Hahn-Platz 3/4, D-24118 Kiel, Germany,.
authors.forename: Thisbe K
authors.initials: TK
authors.lastname: Lindhorst
keywords: Amadori rearrangement; C-mannosides; FimH ligands; bacterial adhesion; docking studies