C-Allyl -D-mannopyranosides were prepared via a variety of routes to determine an optimal route to the anomers. The relative conformational energies of the key intermediate was evaluated by molecular modeling which showed the conventional 4 C1 chair conformation to be the lowest energy conformer. This finding was also confirmed by NMR and X-ray crystallography. The perbenzoylated C-allyl mannoside was also converted into 1,1'-biphenyl analogues using a palladium-catalyzed Heck reaction. Two of the resulting minor reaction products were co-crystallized with the uropathogenic E. coli FimH. Alternatively, the KD of the major and expected Heck product was in the low nM range as measured by SPR. Crystal data showed that the C-linked derivatives efficiently bind in the FimH binding cavity near the so-called hydrophobic tyrosine gate.
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