A Tricatecholic Receptor for Carbohydrate Recognition: Synthesis and Binding Studies (Articolo in rivista)

Type
Label
  • A Tricatecholic Receptor for Carbohydrate Recognition: Synthesis and Binding Studies (Articolo in rivista) (literal)
Anno
  • 2007-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1021/jo0702286 (literal)
Alternative label
  • Martina Cacciarini; Elisa Cordiano; Cristina Nativi; Stefano Roelens (2007)
    A Tricatecholic Receptor for Carbohydrate Recognition: Synthesis and Binding Studies
    in Journal of organic chemistry
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Martina Cacciarini; Elisa Cordiano; Cristina Nativi; Stefano Roelens (literal)
Pagina inizio
  • 3933 (literal)
Pagina fine
  • 3936 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 72 (literal)
Rivista
Note
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Dipartimento di Chimica Organica and Laboratorio di Progettazione Sintesi e Studio di Eterocicli Biologicamente Attivi (HeteroBioLab), Università di Firenze; Istituto di Metodologie Chimiche (IMC), Consiglio Nazionale delle Ricerche (CNR) (literal)
Titolo
  • A Tricatecholic Receptor for Carbohydrate Recognition: Synthesis and Binding Studies (literal)
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 H-1 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. (literal)
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