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Fluorescent cyclodextrins bearing metal binding sites and their use for chemo- and enantioselective sensing of amino acid derivatives

  • Roberto Corradini
  • Cristina Paganuzzi
  • Rosangela Marchelli
  • Sara Pagliari
  • Arnaldo Dossena
  • Alexander Duchateau
Original Article

Abstract

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.

Keywords

Fluorescent sensors Enantioselectivity Amino acids derivatives Cyclodextrins 

Notes

Acknowledgements

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.”).

References

  1. 1.
    Czarnik, A.W. (ed.): Fluorescent Chemosensors for Ion and Molecule Recognition, ACS Symposium Series 538; Washington, DC, American Chemical Society; 1992Google Scholar
  2. 2.
    Pu, L.: Fluorescence of organic molecules in chiral recognition. Chem. Rev. 104, 1687–1716 (2004)CrossRefGoogle Scholar
  3. 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
  4. 4.
    Folmer-Andersen, J.F., Lynch, V.M., Anslyn, E.V.: Colorimetric enantiodiscrimination of α-amino acids in protic media. J. Am. Chem. Soc. 127, 7986–7987 (2005)CrossRefGoogle Scholar
  5. 5.
    Impellizzeri, G., Maccarrone, G., Rizzarelli, E., Vecchio, G., Corradini, R., Marchelli, R.: 6-Deoxy-6-N-histamino-ß-cyclodextrin copper(II) complex, a new enantioselective receptor for aromatic amino acids. Angew. Chem. Int. Ed. Engl. 30, 1348–1349 (1991)CrossRefGoogle Scholar
  6. 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. 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
  8. 8.
    Corradini, R., Dossena, A., Galaverna, G., Marchelli, R., Panagia, A., Sartor, G.: Fluorescent chemosensor for organic guests and copper(II) ion based on dansylethylenetriamine-modified-β-cyclodextrin. J. Org. Chem., 18, 6283–6289 (1997)CrossRefGoogle Scholar
  9. 9.
    Davankov, V.A., Navratil, J.D., Walton, H.F.: Ligand exchange chromatography. Boca Raton, CRC Press (1988)Google Scholar
  10. 10.
    Pagliari, S., Corradini, R., Galaverna, G., Sforza, S., Dossena, A., Marchelli, R.: Enantioselective sensing of amino acids by copper(II) complexes of phenylalanine-based fluorescent β-cyclodextrins. Tetrahedron Lett. 41, 3691–3695 (2000)CrossRefGoogle Scholar
  11. 11.
    Pagliari, S., Corradini, R., Galaverna, G., Sforza, S., Dossena, A., Montalti, M., Prodi, L., Zaccheroni, N., Marchelli, R.: Enantioselective fluorescence sensing of amino acids by modified cyclodextrins: role of the cavity and sensing mechanism. Chem. Eur. J. 10, 2749 (2004)CrossRefGoogle Scholar
  12. 12.
    Corradini, R., Paganuzzi, C., Marchelli, R., Pagliari, S., Sforza, S., Dossena, A., Galaverna, G., Duchateau, A.: Design and synthesis of fluorescent β-cyclodextrins for the enantioselective sensing of α-amino acids. Chirality 15, S30–S39 (2003)CrossRefGoogle Scholar
  13. 13.
    Corradini, R., Paganuzzi, C., Marchelli, R., Pagliari, S., Sforza, S., Dossena, A., Galaverna, G., Duchateau, A.: Fast parallel enantiomeric analysis of unmodified amino acids with fluorescent cyclodextrins. J. Mater. Chem. 15, 2741–2746 (2005)CrossRefGoogle Scholar
  14. 14.
    Fava Gasparri, G., Ferrari Belicchi, M., Corradini, R., Marchelli, R., Dossena, A.: The effect of N2-mono- and dimethylation on the crystal structures of bis[(S)-phenylalaninamidato]copper(II) complexes. Tetrahedron Asymmetry 3, 387–400 (1992)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  • Roberto Corradini
    • 1
  • Cristina Paganuzzi
    • 1
  • Rosangela Marchelli
    • 1
  • Sara Pagliari
    • 1
    • 3
  • Arnaldo Dossena
    • 1
  • Alexander Duchateau
    • 2
  1. 1.Dipartimento di Chimica Organica e IndustrialeUniversità di Parma Parco Area delle ScienzeParmaItaly
  2. 2.DSM ResearchGeleenThe Netherlands
  3. 3.Callegari S.p.A.ParmaItaly

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