Coordination properties of 3-functionalized beta-cyclodextrins. Thermodynamic stereoselectivity of copper(II) complexes of the A,B-diamino derivative and its exploitation in LECE.
The bis-amino AB derivative of beta-cyclodextrin on the secondary rim was synthesised and spectroscopically characterised by different techniques. Its binary systems both with protons and copper(II) were thermodynamically characterised by pH-metric potentiometry. In addition the ternary systems with each of the enantiomers of tryptophan and alanine were investigated. A thermodynamic stereoselectivity was observed for the tryptophan enantiomers and this was exploited to separate them by capillary electrophoresis through a ligand exchange mechanism (LECE). LECE separation of racemates of phenylalanine and tyrosine was also obtained.
Cucinotta
Vincenzo
V
Department of Chemical Sciences, University of Catania, viale A. Doria 6, 95125, Catania, Italy.
Giuffrida
Alessandro
A
Maccarrone
Giuseppe
G
Messina
Marianna
M
Puglisi
Antonino
A
Rizzarelli
Enrico
E
Vecchio
Graziella
G
D001665:Binding Sites; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D003300:Copper / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D008024:Ligands; D008969:Molecular Sequence Data; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013816:Thermodynamics; D047392:beta-Cyclodextrins / Q000737:chemistry*
D008024:Ligands; D009942:Organometallic Compounds; D047392:beta-Cyclodextrins; D003300:Copper