Synthesis of some amino and carboxy analogs of galabiose; evaluation as inhibitors of the pilus protein PapGJ96 from Escherichia coli

Carbohydr Res. 1998 Feb;307(3-4):233-42. doi: 10.1016/s0008-6215(98)00020-2.

Abstract

The 2'-amino-2'-deoxy, 6-amino-6-deoxy, and 6-carboxy analogs of the reference inhibitors 2-(trimethylsilyl)ethyl (alpha-D-galactopyranosyl)-(1-->4)-ss-D-galactopyranoside were synthesized and evaluated as inhibitors of the binding of the Escherichia coli-derived pilus protein PapGj96, using an ELISA assay. The inhibitory efficiencies (Krel; relative to the reference inhibitor) were: 157,13, and < 8, respectively. The results support the previously proposed combining site model, where the protein carries a negatively charged amino acid residue near HO-2' and HO-6 of the galabio-side.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Adhesins, Escherichia coli / metabolism*
  • Disaccharides / chemical synthesis*
  • Disaccharides / pharmacology*
  • Enzyme-Linked Immunosorbent Assay
  • Escherichia coli / metabolism*
  • Fimbriae Proteins*
  • Fimbriae, Bacterial / metabolism*

Substances

  • Adhesins, Escherichia coli
  • Disaccharides
  • PapG protein, E coli
  • 4-O-alpha-D-galactopyranosyl-D-galactose
  • Fimbriae Proteins