Journal
CHEMMEDCHEM
Volume 2, Issue 9, Pages 1328-1338Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cmdc.200700100
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Funding
- NIGMS NIH HHS [GM62116] Funding Source: Medline
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Pseudomonas aeruginosa is an opportunistic bacterium showing increasing resistance to antibiotics and consequently represents elevated threatening problems in hospital environments, particularly for cystic fibrosis patients. The use of glycomimetics as an anti-adhesive strategy against microorganisms may complement the use of antibiotics. PA-IIL lectin (LecB) from P. aeruginosa constitutes an appealing target for antibacterial agents, as it has been proposed to play a key role in binding to airway epithelia and/or to be involved in biofilm formation. The lectin has an unusually high affinity for L-fucose and related oligosaccharides. In the work presented herein, the disaccharide alpha Fuc1-4GIcNAc is used as a scaffold toward the synthesis of a series of glycomimetic derivatives. Microcolorimetry and structural studies indicate that several of the derivatives are potent inhibitors of the lectin, with affinity in the some range as the best known natural ligand, Lewis a, and could represent interesting leads for the development of future antibacterial compounds.
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