Metabolically stable arabinose 5-phosphate analogues possessing phosphate mimetic groups at the 5-position were synthesized and evaluated by saturation-transfer-difference (STD) NMR studies for their ability to interact with arabinose 5-phosphate isomerase. Isosteric methylphosphonate 1 and (difluoromethyl)phosphonate 3 were recognised and bound by the catalytic pocket of the enzyme. The synthesized compounds were tested in vivo on E. coli and P. aeruginosa strains in order to evaluate their antibacterial activity.
Gabrielli, L., Airoldi, C., Sperandeo, P., Gianera, S., Polissi, A., Nicotra, F., et al. (2013). Phosphonate Analogues of Arabinose 5-Phosphate: Putative Ligands for Arabinose 5-Phosphate Isomerases. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013(34), 7776-7784 [10.1002/ejoc.201300887].
Phosphonate Analogues of Arabinose 5-Phosphate: Putative Ligands for Arabinose 5-Phosphate Isomerases
GABRIELLI, LUCA;AIROLDI, CRISTINA;SPERANDEO, PAOLA;GIANERA, SERENA;POLISSI, ALESSANDRA;NICOTRA, FRANCESCO;CIPOLLA, LAURA FRANCESCA
2013
Abstract
Metabolically stable arabinose 5-phosphate analogues possessing phosphate mimetic groups at the 5-position were synthesized and evaluated by saturation-transfer-difference (STD) NMR studies for their ability to interact with arabinose 5-phosphate isomerase. Isosteric methylphosphonate 1 and (difluoromethyl)phosphonate 3 were recognised and bound by the catalytic pocket of the enzyme. The synthesized compounds were tested in vivo on E. coli and P. aeruginosa strains in order to evaluate their antibacterial activity.
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