Fluorescent cyclodextrins bearing metal binding sites and their use for chemo- and enantioselective sensing of amino acid derivatives
- 104 Downloads
Ditopic receptors based on cyclodextrins bearing a metal binding site were used as enantioselective fluorescence sensors, which were able to generate different responses in the presence of d- or l-amino acids. The performances of the selectors as a function of their structure were evaluated, and the same analysis was extended to other analytes. In this work, this approach is used for the enantiomers of a series of amino acid derivatives and in particular of 2-aminocaprolactam. The results showed that the ability of these sensors to perform enantiomeric analysis can be extended to other analytes of interest in organic synthesis such as amino acid amides and α-aminolactams.
KeywordsFluorescent sensors Enantioselectivity Amino acids derivatives Cyclodextrins
This work was partially supported by DSM and by grants from the Ministero dell’Istruzione, Università e Ricerca (PRIN2005 project: “Molecular and enantiomeric recognition of biologically active substances in natural systems”, and FIRB project RBNE01KZZM_006: “Study of multifunctional microsystems for chemical and biochemical determinations in complex biological matrixes.”).
- 1.Czarnik, A.W. (ed.): Fluorescent Chemosensors for Ion and Molecule Recognition, ACS Symposium Series 538; Washington, DC, American Chemical Society; 1992Google Scholar
- 3.Wang, D., Liu, T.J., Zhang, W.C., Slaven W.T. IV, Li, C.J.: Enantiomeric discrimination of chiral amines with new fluorescent chemosensors. Chem. Commun. 1747–1748 (1998)Google Scholar
- 6.Corradini, R., Dossena, A., Impellizzeri, G., Maccarrone, G., Marchelli, R., Rizzarelli, E., Sartor, G., Vecchio, G.: Chiral recognition and separation of amino acids by means of a copper(II) complex of histamine monofunctionalized β-cyclodextrin. J. Am. Chem. Soc. 116, 10267–10274 (1994)CrossRefGoogle Scholar
- 7.Corradini, R., Dossena, A., Marchelli, R., Panagia, A., Sartor, G., Saviano, M., Lombardi, A., Pavone, V.: A modified cyclodextrin with a fully encapsulated dansyl group: self inclusion in the solid state and in solution. Chem. Eur. J., 2, 373–381 (1996)Google Scholar
- 9.Davankov, V.A., Navratil, J.D., Walton, H.F.: Ligand exchange chromatography. Boca Raton, CRC Press (1988)Google Scholar