Molecular recognition of carbohydrates is at the heart of different events of paramount biomedical interest. In this context, the employment of sugar mimics as enzyme inhibitors or molecular probes has been widely developed in the last years. Among them, we herein present our advances in the use of fluorine-containing carbasugars for the characterization at molecular level of different receptor/sugar recognition events [1]. In fact, the replacement of the ring-oxygen by a CHF or CF2 group could somehow restore the typical stereo-electronic effects occurring in natural sugar, [2] although might also influence the conformational behavior of these molecules [3].
Therefore, we have applied 19F and 1H homo and heteronuclear solution NMR methods to determine the conformational properties of a series of fluorine-containing carbasugars which differ in the stereochemistry at different carbon atoms and present either single or dual fluorine substitution. Mono- and di-saccharide entities have been scrutinized.
Additionally, their interaction abilities towards different protein receptors have been explored using NMR and computational techniques. Special emphasis has been placed to unravel their possible involvement in key intermolecular forces for sugar recognition, such as CH-π and hydrogen bond interactions [4].
[1] A. Deleuze, C. Menozzi, M. Sollogoub, P. Sinay. Angew. Chem.. 2004, 48, 6848-6851
[2] E. Leclerc, M. Sollogoub et al. Chem. Soc. Rev. 2013, doi:10.1039/C2CS35403A,
[3] J. Jiménez-Barbero, M.Sollogoub et al. Chem. Asian J. 2008, 3, 51-58
[4] C. Dalvit, A. Vulpetti CHEMMEDCHEM, 2012, 7, 262-272
