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Amino Acids

, Volume 40, Issue 4, pp 1065–1075 | Cite as

Novel highly emissive non-proteinogenic amino acids: synthesis of 1,3,4-thiadiazolyl asparagines and evaluation as fluorimetric chemosensors for biologically relevant transition metal cations

  • Cátia I. C. Esteves
  • M. Manuela M. Raposo
  • Susana P. G. Costa
Original Article

Abstract

Highly emissive heterocyclic asparagine derivatives bearing a 1,3,4-thiadiazolyl unit at the side chain, functionalised with electron donor or acceptor groups, were synthesised and evaluated as amino acid-based fluorimetric chemosensors for metal cations, such as Cu2+, Zn2+, Co2+ and Ni2+. The results suggest that there is a strong interaction through the donor heteroatoms at the side chain of the various asparagine derivatives, with high sensitivity towards Cu2+ in a ligand–metal complex with 1:2 stoichiometry. Association constants and detection limits for Cu2+ were calculated. The photophysical and metal ion sensing properties of these asparagine derivatives confirm their potential as fluorimetric chemosensors and suggest that they can be suitable for incorporation into chemosensory peptidic frameworks.

Keywords

Non-proteinogenic amino acids Asparagine Thiadiazole Fluorescence Chemosensors Transition metals 

Notes

Acknowledgments

Thanks are due to the Fundação para a Ciência e Tecnologia (Portugal) for financial support through project PTDC/QUI/66250/2006 (FCOMP-01-0124-FEDER-007428) and a research grant to C. Esteves. The NMR spectrometer Bruker Avance III 400 is part of the National NMR Network and was purchased within the framework of the National Program for Scientific Re-equipment, contract REDE/1517/RMN/2005 with funds from POCI 2010 (FEDER) and FCT.

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Copyright information

© Springer-Verlag 2010

Authors and Affiliations

  • Cátia I. C. Esteves
    • 1
  • M. Manuela M. Raposo
    • 1
  • Susana P. G. Costa
    • 1
  1. 1.Centro de QuímicaUniversidade do MinhoBragaPortugal

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