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Evaluation of an unnatural amino acid as a fluorimetric chemosensor for anion recognition

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Resumo:Molecular recognition is the basis for most biological functions and in recent years the research on compounds capable of recognizing and binding organic and inorganic molecules involved in biological pathways has evolved to mimic as much as possible the natural mechanisms of organization [1]. The development of artificial receptors for recognizingcationic, neutral, and anionic species is growing and has attracted much interest in molecular recognition study and supramolecular chemistry because they play an important role in a wide range of biological, environmental, and chemical processes [2]. The insertion of coded and unnatural amino acids into the backbone of both natural and synthetic polymers can lead to the development of macromolecules possessing biomimetic characteristics, with unique structural and biological properties. By synthetic manipulation at the side chain of the coded amino acids, new functions and functional relationships can be generated as well as altered physicochemical properties, such as luminescence, conducting ability, higher thermal stability and metal ion and other analytes recognition ability, among other properties [3]. Anion coordination by natural amino acids can arise from side chain OH and NH groups (in serine, threonine, tyrosine or arginine and tryptophan, respectively), as well from additional binding withamide NH groups from the backbone, which act as hydrogen-bond donors to the anion [4]. Following our research interests on the synthesis and application of fluorimetric probes for anions and metal cations based on heterocycles and amino acids[5], we now report the evaluation of an unnatural alanine derivative as a fluorimetric chemosensor for the recognition of anions with analytical, biological, and medicinal relevance, through the introduction of oxygen and nitrogen heterocycles as recognition/reporting units in an alanine core. Benzoxazolyl-alanine 1with an imidazole was evaluated for its ability to respond, viachanges in the fluorescence spectra, in the presence of organic and inorganic anions such as halides, through spectrofluorometrictitrations.
Autores principais:Esteves, Cátia I. C.
Outros Autores:Raposo, M. Manuela M.; Costa, Susana P. G.
Ano:2012
País:Portugal
Tipo de documento:outro
Tipo de acesso:acesso restrito
Instituição associada:Universidade do Minho
Idioma:inglês
Origem:RepositóriUM - Universidade do Minho

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