Beilstein Journal of Organic Chemistry (Jun 2015)

Are D-manno-configured Amadori products ligands of the bacterial lectin FimH?

  • Tobias-Elias Gloe,
  • Insa Stamer,
  • Cornelia Hojnik,
  • Tanja M. Wrodnigg,
  • Thisbe K. Lindhorst

DOI
https://doi.org/10.3762/bjoc.11.123
Journal volume & issue
Vol. 11, no. 1
pp. 1096 – 1104

Abstract

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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.

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