Issue 27-28, 2005
From the journal:

Journal of Materials Chemistry

Fast parallel enantiomeric analysis of unmodified amino acids by sensing with fluorescent β-cyclodextrins

Roberto Corradini,*a   Cristina Paganuzzi,a   Rosangela Marchelli,a   Sara Pagliari,†a   Stefano Sforza,a   Arnaldo Dossena,a   Gianni Galavernaa  and  Alexander Duchateaub  

* Corresponding authors

a Dipartimento di Chimica Organica e Industriale, Università di Parma Parco Area delle Scienze 17/A, I-43100 Parma, Italy
E-mail: roberto.corradini@unipr.it
Fax: +39-0521-905472
Tel: +39-0521-905406

b DSM Research, P.O. Box 18 - 6160 MD Geleen, The Netherlands

Abstract

Modified cyclodextrins bearing a metal binding site and a dansyl fluorophore 6-deoxy-6-N-(Nα-[(5-dimethylamino-1-naphthalenesulfonyl)aminoethyl]-aminocylamino-β-cyclodextrin, containing L-Phe (S-1), L-PhGly (S-2) or L-Pro (S-3) moieties, were used as enantioselective fluorescence sensors for the discrimination of enantiomers of the amino acids valine and proline, according to a ligand exchange mechanism. The best conditions to perform enantiomeric analyses were studied and a fast protocol using fluorescence quenching by the copper(II)/amino acid complexes in a fluorescence microplate reader was developed, allowing the detection of samples with high enantiomeric excess. Calibration of the fluorescence response as a function of enantiomeric composition was obtained using the Stern–Volmer model; the calibration curves showed good linearity, allowing fast evaluation of enantiomeric excess within 6% error. Two calibration curves and triplicate analyses of six valine samples were performed in two minutes.

Graphical abstract: Fast parallel enantiomeric analysis of unmodified amino acids by sensing with fluorescent β-cyclodextrins

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Article information

DOI
https://doi.org/10.1039/B418369J
Article type
Paper
Submitted
07 Dec 2004
Accepted
14 Feb 2005
First published
28 Feb 2005

J. Mater. Chem., 2005,15, 2741-2746

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Fast parallel enantiomeric analysis of unmodified amino acids by sensing with fluorescent β-cyclodextrins

R. Corradini, C. Paganuzzi, R. Marchelli, S. Pagliari, S. Sforza, A. Dossena, G. Galaverna and A. Duchateau, J. Mater. Chem., 2005, 15, 2741 DOI: 10.1039/B418369J

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