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...

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Bibliographic Details
Published in:Dalton transactions : an international journal of inorganic chemistry 2005-08 (16), p.2731-2736
Main Authors: Cucinotta, Vincenzo, Giuffrida, Alessandro, Maccarrone, Giuseppe, Messina, Marianna, Puglisi, Antonino, Rizzarelli, Enrico, Vecchio, Graziella
Format: Article
Language:English
Subjects:
beta-Cyclodextrins - chemistry
Binding Sites
Carbohydrate Conformation
Carbohydrate Sequence
Copper - chemistry
Hydrogen-Ion Concentration
Ligands
Molecular Sequence Data
Organometallic Compounds - chemical synthesis
Organometallic Compounds - chemistry
Stereoisomerism
Thermodynamics
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Summary: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.
ISSN:1477-9226
1477-9234
DOI:10.1039/b506080j