Synthesis of some amino and carboxy analogs of galabiose; evaluation as inhibitors of the pilus protein PapGJ96 from Escherichia coli.
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.
Center for Chemistry and Chemical Engineering, Lund University, Sweden.
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Magnusson
D018830:Adhesins, Escherichia coli / Q000378:metabolism*; D004187:Disaccharides / Q000138:chemical synthesis* / Q000494:pharmacology*; D004797:Enzyme-Linked Immunosorbent Assay; D004926:Escherichia coli / Q000378:metabolism*; D036781:Fimbriae Proteins; D010861:Fimbriae, Bacterial / Q000378:metabolism*
D018830:Adhesins, Escherichia coli; D004187:Disaccharides; C092426:PapG protein, E coli; C032103:4-O-alpha-D-galactopyranosyl-D-galactose; D036781:Fimbriae Proteins