6533b829fe1ef96bd128a55e

RESEARCH PRODUCT

A spectrofluorimetric study of binary fluorophore-cyclodextrin complexes used as chiral selectors

Francesca D'annaRenato NotoPaolo Lo MeoSerena RielaMichelangelo Gruttadauria

subject

chemistry.chemical_classificationFluorophoreCyclodextrinChemistryOrganic ChemistrySettore CHIM/06 - Chimica OrganicaBiochemistryFluorescenceAnthraquinoneFluorescence spectroscopychemistry.chemical_compoundDrug DiscoveryXanthonePhysical chemistryPyreneOrganic chemistrycyclodextrin binding abilityTernary operation

description

Abstract Six binary complexes between three fluorophores (pyrene, xanthone and anthraquinone) and β-cyclodextrin (β-CD) or heptakis-(6-amino)-(6-deoxy)-β-cyclodextrin (am-β-CD) were tested at two pH values (8.0 and 9.0) as chiral selectors for three α-amino acids chosen as model. The conditional constant (β2T) values for ternary complexes (fluorophore-CD-amino acid), determined by means of fluorescence spectroscopy, showed that the binary complexes are suitable receptors for chiral recognition. The effect of α-amino acids on stability and stoichiometric ratio of the binary complexes has also been studied. The binary complexes were in most cases stabilized by adding the ternary agent. The trend of stoichiometric ratios found is supported by variations in fluorescence spectra. Those relative to pyrene ( Py ) show little changes going from binary to ternary complexes, while those recorded in the presence of xanthone ( Xan ) give the most significant variations underlining a deep reorganization of guest. Anthraquinone ( Aq ) shows an intermediate behavior.

yearjournalcountryeditionlanguage
2005-05-01
10.1016/j.tet.2005.03.013http://hdl.handle.net/10447/23908