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Recognition of metallic ions by unnatural amino acids bearing nitrogen and oxygen heterocycles : synthesis and interaction studies with relevant metals

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Resumo:Molecular recognition phenomena play important roles in a variety of physical, chemical, and biological events, and are a field of convergence of knowledge from organic, inorganic, analytical and physical chemistry. Therefore, in recent years there have been considerable efforts on the design, synthesis and application of novel fluorescent molecular probes that selectively and specifically respond to the presence of specific analytes (ions and neutral molecules), as fluorescence allows the highest sensitivity (up to detection of single molecules) in sensory applications [1]. Metal ions are key parts in all aspects of human life, and recently amino acids have attracted great interest for constructing bio-analogous metal-organic frameworks materials since amino acid residues are the origin for the highly selective substrate- binding ability of proteins [2]. Metal coordination to amino acids and peptides could give rise to metal-organic frameworks in which amino acid residues may offer flexible hydrogen bonding to induce molecular recognition. The design of peptides that coordinate metals, by incorporation of modified amino acids, has potential applications in the study of protein-protein interactions mediated by metals, protein binding to nanoparticles and metal surfaces, and the development of selective chemosensors for metals for use in vitro and in vivo [3]. Bearing these facts in mind and following our research interests that include the synthesis and application of fluorimetric probes for metallic ions based on heterocycles and amino acids [4], we now report the synthesis and evaluation of unnatural alanine derivatives as fluorimetric chemosensors for the recognition of metallic ions through the introduction of five-membered nitrogen and oxygen heterocycles as coordinating/reporting units in a benzoxazolyl-alanine core in order to obtain new chemosensors
Autores principais:Costa, Susana P. G.
Outros Autores:Ferreira, R. Cristina M.; Afonso, E. R. M.; Raposo, M. Manuela M.
Ano:2011
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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author Costa, Susana P. G.
author2 Ferreira, R. Cristina M.
Afonso, E. R. M.
Raposo, M. Manuela M.
author2_role author
author
author
author_facet Costa, Susana P. G.
Ferreira, R. Cristina M.
Afonso, E. R. M.
Raposo, M. Manuela M.
author_role author
contributor_name_str_mv RepositóriUM - Universidade do Minho
country_str PT
creators_json_txt [{\"Person.name\":\"Costa, Susana P. G.\"},{\"Person.name\":\"Ferreira, R. Cristina M.\"},{\"Person.name\":\"Afonso, E. R. M.\"},{\"Person.name\":\"Raposo, M. Manuela M.\"}]
datacite.contributors.contributor.contributorName.fl_str_mv RepositóriUM - Universidade do Minho
datacite.creators.creator.creatorName.fl_str_mv Costa, Susana P. G.
Ferreira, R. Cristina M.
Afonso, E. R. M.
Raposo, M. Manuela M.
datacite.date.Accepted.fl_str_mv 2011-01-01T00:00:00Z
datacite.date.available.fl_str_mv 2012-03-16T18:56:46Z
datacite.date.embargoed.fl_str_mv 2012-03-16T18:56:46Z
datacite.rights.fl_str_mv http://purl.org/coar/access_right/c_16ec
datacite.titles.title.fl_str_mv Recognition of metallic ions by unnatural amino acids bearing nitrogen and oxygen heterocycles : synthesis and interaction studies with relevant metals
dc.contributor.none.fl_str_mv RepositóriUM - Universidade do Minho
dc.creator.none.fl_str_mv Costa, Susana P. G.
Ferreira, R. Cristina M.
Afonso, E. R. M.
Raposo, M. Manuela M.
dc.date.Accepted.fl_str_mv 2011-01-01T00:00:00Z
dc.date.available.fl_str_mv 2012-03-16T18:56:46Z
dc.date.embargoed.fl_str_mv 2012-03-16T18:56:46Z
dc.format.none.fl_str_mv application/pdf
dc.identifier.none.fl_str_mv https://hdl.handle.net/1822/17873
dc.language.none.fl_str_mv eng
dc.publisher.none.fl_str_mv Elsevier
dc.rights.none.fl_str_mv http://purl.org/coar/access_right/c_16ec
dc.title.fl_str_mv Recognition of metallic ions by unnatural amino acids bearing nitrogen and oxygen heterocycles : synthesis and interaction studies with relevant metals
dc.type.none.fl_str_mv http://purl.org/coar/resource_type/c_1843
description Molecular recognition phenomena play important roles in a variety of physical, chemical, and biological events, and are a field of convergence of knowledge from organic, inorganic, analytical and physical chemistry. Therefore, in recent years there have been considerable efforts on the design, synthesis and application of novel fluorescent molecular probes that selectively and specifically respond to the presence of specific analytes (ions and neutral molecules), as fluorescence allows the highest sensitivity (up to detection of single molecules) in sensory applications [1]. Metal ions are key parts in all aspects of human life, and recently amino acids have attracted great interest for constructing bio-analogous metal-organic frameworks materials since amino acid residues are the origin for the highly selective substrate- binding ability of proteins [2]. Metal coordination to amino acids and peptides could give rise to metal-organic frameworks in which amino acid residues may offer flexible hydrogen bonding to induce molecular recognition. The design of peptides that coordinate metals, by incorporation of modified amino acids, has potential applications in the study of protein-protein interactions mediated by metals, protein binding to nanoparticles and metal surfaces, and the development of selective chemosensors for metals for use in vitro and in vivo [3]. Bearing these facts in mind and following our research interests that include the synthesis and application of fluorimetric probes for metallic ions based on heterocycles and amino acids [4], we now report the synthesis and evaluation of unnatural alanine derivatives as fluorimetric chemosensors for the recognition of metallic ions through the introduction of five-membered nitrogen and oxygen heterocycles as coordinating/reporting units in a benzoxazolyl-alanine core in order to obtain new chemosensors
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person_str_mv Costa, Susana P. G.
Ferreira, R. Cristina M.
Afonso, E. R. M.
Raposo, M. Manuela M.
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spelling engElsevierporMolecular recognition phenomena play important roles in a variety of physical, chemical, and biological events, and are a field of convergence of knowledge from organic, inorganic, analytical and physical chemistry. Therefore, in recent years there have been considerable efforts on the design, synthesis and application of novel fluorescent molecular probes that selectively and specifically respond to the presence of specific analytes (ions and neutral molecules), as fluorescence allows the highest sensitivity (up to detection of single molecules) in sensory applications [1]. Metal ions are key parts in all aspects of human life, and recently amino acids have attracted great interest for constructing bio-analogous metal-organic frameworks materials since amino acid residues are the origin for the highly selective substrate- binding ability of proteins [2]. Metal coordination to amino acids and peptides could give rise to metal-organic frameworks in which amino acid residues may offer flexible hydrogen bonding to induce molecular recognition. The design of peptides that coordinate metals, by incorporation of modified amino acids, has potential applications in the study of protein-protein interactions mediated by metals, protein binding to nanoparticles and metal surfaces, and the development of selective chemosensors for metals for use in vitro and in vivo [3]. Bearing these facts in mind and following our research interests that include the synthesis and application of fluorimetric probes for metallic ions based on heterocycles and amino acids [4], we now report the synthesis and evaluation of unnatural alanine derivatives as fluorimetric chemosensors for the recognition of metallic ions through the introduction of five-membered nitrogen and oxygen heterocycles as coordinating/reporting units in a benzoxazolyl-alanine core in order to obtain new chemosensorsapplication/pdfporRecognition of metallic ions by unnatural amino acids bearing nitrogen and oxygen heterocycles : synthesis and interaction studies with relevant metalsCosta, Susana P. G.Ferreira, R. Cristina M.Afonso, E. R. M.Raposo, M. Manuela M.HostingInstitutionOrganizationalRepositóriUM - Universidade do Minhoe-mailmailto:repositorium@usdb.uminho.ptrepositorium@usdb.uminho.pt2012-03-16T18:56:46Z20112011-01-01T00:00:00ZHandlehttps://hdl.handle.net/1822/17873http://purl.org/coar/access_right/c_16ecrestricted access199984 bytesother research producthttp://purl.org/coar/resource_type/c_1843otherhttp://purl.org/coar/access_right/c_16ecapplication/pdffulltexthttps://repositorium.uminho.pt/bitstreams/52dfc626-5a72-4f8b-8e7f-159f964b0f9a/download
spellingShingle Recognition of metallic ions by unnatural amino acids bearing nitrogen and oxygen heterocycles : synthesis and interaction studies with relevant metals
Costa, Susana P. G.
status SINGLETON
title Recognition of metallic ions by unnatural amino acids bearing nitrogen and oxygen heterocycles : synthesis and interaction studies with relevant metals
title_full Recognition of metallic ions by unnatural amino acids bearing nitrogen and oxygen heterocycles : synthesis and interaction studies with relevant metals
title_fullStr Recognition of metallic ions by unnatural amino acids bearing nitrogen and oxygen heterocycles : synthesis and interaction studies with relevant metals
title_full_unstemmed Recognition of metallic ions by unnatural amino acids bearing nitrogen and oxygen heterocycles : synthesis and interaction studies with relevant metals
title_short Recognition of metallic ions by unnatural amino acids bearing nitrogen and oxygen heterocycles : synthesis and interaction studies with relevant metals
title_sort Recognition of metallic ions by unnatural amino acids bearing nitrogen and oxygen heterocycles : synthesis and interaction studies with relevant metals
url https://hdl.handle.net/1822/17873
visible 1