title: A tricatecholic receptor for carbohydrate recognition: synthesis and binding studies.
abstract: A new tripodal receptor bearing three catechol subunits on a benzene platform has been synthesized in four steps from 1,3,5-triethylbenzene and pyrogallol. The binding ability of the tricatecholic receptor was investigated toward several monosaccharides in CDCl3, where multiple equilibria were detected, and compared to that of a previously reported trisureidic receptor of analogous structure. Association constants were measured by 1H NMR titrations, and the corresponding affinities were assessed through the BC50 parameter, a binding descriptor univocally defining the affinity of a host for a guest in multi-equilibrium systems. Results show that the tripodal catecholic receptor binds the octyl glycosides with affinities ranging from 0.87 to 5.2 mM and with a 6-fold selectivity factor for the alpha-mannoside over the beta-glucoside. Although the affinity for glycosides was not appreciably improved with respect to the ureidic receptor, a significant change in selectivity was obtained by the H-bonding group replacement.
authors: Dipartimento di Chimica Organica and Laboratorio di Progettazione Sintesi e Studio di Eterocicli Biologicamente Attivi (HeteroBioLab), Università di Firenze, Italy.
authors: Martina
authors: M
authors: Cacciarini
authors: Elisa
authors: E
authors: Cordiano
authors: Cristina
authors: C
authors: Nativi
authors: Stefano
authors: S
authors: Roelens
mesh_terms: D002241:Carbohydrates / Q000737:chemistry*; D002396:Catechols / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D002241:Carbohydrates; D002396:Catechols; C034221:catechol