title: Bi- and trivalent glycopeptide mannopyranosides as inhibitors of type 1 fimbriae-mediated bacterial adhesion: variation of valency, aglycon and scaffolding.
abstract: In order to test relevant structural parameters for effective inhibition of mannose-specific bacterial adhesion, bi- and trivalent glycopeptide α-D-mannopyranosides were synthesized that differ in their conformational properties as well as in the spatial arrangement of attached mannosyl residues. They were tested in an inhibition adhesion assay with fluorescent Escherichia coli bacteria and testing results were referenced to the inhibitory potency of methyl α-D-mannopyranoside. It was shown, that besides the nature of the mannoside aglycon moiety, scaffolding of α-D-mannopyranosides on a peptide backbone was important for the performance of the synthesized glycopeptides as inhibitors of bacterial adhesion.
authors.affiliation: Otto Diels Institute of Organic Chemistry, Christiana Albertina University of Kiel, Otto-Hahn-Platz 3/4, 24098 Kiel, Germany.
authors.forename: Alexander
authors.initials: A
authors.lastname: Schierholt
authors.forename: Mirja
authors.initials: M
authors.lastname: Hartmann
authors.forename: Thisbe K
authors.initials: TK
authors.lastname: Lindhorst
mesh_terms: D018830:Adhesins, Escherichia coli / Q000737:chemistry / Q000378:metabolism*; D001422:Bacterial Adhesion / Q000187:drug effects*; D002236:Carbohydrate Conformation; D002855:Chromatography, Thin Layer; D004926:Escherichia coli / Q000737:chemistry / Q000378:metabolism*; D036781:Fimbriae Proteins / Q000737:chemistry / Q000378:metabolism*; D010861:Fimbriae, Bacterial / Q000187:drug effects* / Q000378:metabolism; D006020:Glycopeptides / Q000138:chemical synthesis / Q000494:pharmacology; D049452:Green Fluorescent Proteins / Q000032:analysis; D009682:Magnetic Resonance Spectroscopy; D008358:Mannose / Q000138:chemical synthesis / Q000494:pharmacology; D008362:Mannosides / Q000737:chemistry; D008766:Methylmannosides / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D018830:Adhesins, Escherichia coli; D006020:Glycopeptides; D008362:Mannosides; D008766:Methylmannosides; C058769:fimH protein, E coli; D049452:Green Fluorescent Proteins; D036781:Fimbriae Proteins; C008466:methylmannoside; D008358:Mannose