Enantioselective sensing of amino acids by copper(II) complexes of phenylalanine-based fluorescent beta-cyclodextrins

Citation
S. Pagliari et al., Enantioselective sensing of amino acids by copper(II) complexes of phenylalanine-based fluorescent beta-cyclodextrins, TETRAHEDR L, 41(19), 2000, pp. 3691-3695
Citations number
21
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
0040-4039 → ACNP
Volume
41
Issue
19
Year of publication
2000
Pages
3691 - 3695
Database
ISI
SICI code
0040-4039(20000506)41:19<3691:ESOAAB>2.0.ZU;2-B
Abstract
The synthesis and full characterisation of two modified cyclodextrins 6-deo xy-6-N-[N-alpha-(N-2-dansylaminoethyl)-R-(or S)-phenylalaninamide]-beta-cyc lodextrin, containing a metal binding site and a dansyl fluorophore, are de scribed. Both cyclodextrins were shown to form copper(II) complexes with fl uorescence quenching. Addition of D- or L-amino acids to the copper(II) com plexes induced a 'switch on' of the fluorescence which was enantioselective for Pro, Phe and Trp. The enantioselective fluorescence effect was used fo r the determination of the optical purity of proline. (C) 2000 Elsevier Sci ence Ltd. All rights reserved.