Utilize este identificador para referenciar este registo:
https://hdl.handle.net/1822/22066
Registo completo
Campo DC | Valor | Idioma |
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dc.contributor.author | Ferreira, Paula M. T. | - |
dc.contributor.author | Monteiro, Luís S. | - |
dc.contributor.author | Castanheira, Elisabete M. S. | - |
dc.contributor.author | Pereira, Goreti | - |
dc.contributor.author | Frost, Christopher G. | - |
dc.date.accessioned | 2012-12-21T18:54:43Z | - |
dc.date.available | 2012-12-21T18:54:43Z | - |
dc.date.issued | 2013 | - |
dc.identifier.issn | 1434-193X | por |
dc.identifier.uri | https://hdl.handle.net/1822/22066 | - |
dc.description.abstract | Several arylalanine derivatives containing fluorescent groups were prepared in good yields using a rhodium catalysed conjugate addition of arylboronic acids to N,N-diprotected and N-monoprotected dehydroalanines. The best conditions for these reactions require the use of an excess of aryl boronic acid (4 equiv.), [Rh(COD)2]BF4 as catalyst and CsF as base in dioxane:H2O (10:1) at 110 ºC. These conditions were also applied to several dipeptides with dehydroalanine residues. The photophysical properties of some of the arylalanines were studied in three solvents of different polarity. Due to the absence of the, double bond, the absorption and fluorescence emission of the new compounds are dominated by the photophysical properties of the polycyclic aromatic fluorophores (naphthalene, phenanthrene and pyrene). Considering the relatively high fluorescence quantum yield of these compounds, some of them may be useful as fluorescent markers for peptides and proteins. | por |
dc.description.sponsorship | Thanks are due to the Foundation for Science and Technology (FCT, Portugal), Quadro de Referencia Estrategico Nacional (QREN), and Fundo Europeu de Desenvolvimento Regional/Uniao Europeia (FEDER/EU) for financial support through the research centers, CQ/UM [PEst-C/QUI/UI0686/2011 (FCOMP-01-0124-FEDER-022716)] and CFUM [PEst-C/FIS/UI0607/2011 (F-COMP-01-0124-FEDER-022711)], and project PTDC/QUI/81238/2006 (cofinanced by Fundo Europeu de Desenvolvimento Regional/Programa Operacional Fatores de Competitividade (FEDER/COMPETE), ref. FCOMP-01-0124-FEDER-007467). G. P. acknowledges her PhD grant from Fundacao para a Ciencia e a Tecnologia (FCT), Programa Operacional Potencial Humano/Quadro de Referencia Estrategico Nacional (POPH-QREN), Fundo Social Europeu (FSE) (SFRH/BD/38766/2007). | por |
dc.language.iso | eng | por |
dc.publisher | Wiley-VCH Verlag | por |
dc.relation | info:eu-repo/grantAgreement/FCT/5876-PPCDTI/81238/PT | - |
dc.rights | openAccess | por |
dc.subject | Dehydroalanines | por |
dc.subject | Rhodium-catalysis | por |
dc.subject | Arylboronic acids | por |
dc.subject | Conjugate addition | por |
dc.subject | Fluorescent marker | por |
dc.subject | Amino acids | por |
dc.subject | Rhodium | por |
dc.subject | Homogeneous catalysis | por |
dc.subject | Fluorescent probes | por |
dc.title | Synthesis of fluorescent alanines by a rhodium catalysed conjugate addition of arylboronic acids to dehydroalanine derivatives | por |
dc.type | article | por |
dc.peerreviewed | yes | por |
dc.relation.publisherversion | http://dx.doi.org/10.1002/ejoc.201201198 | - |
sdum.publicationstatus | published | por |
oaire.citationStartPage | 550 | por |
oaire.citationEndPage | 556 | por |
oaire.citationIssue | 3 | por |
oaire.citationTitle | European Journal of Organic Chemistry | por |
dc.identifier.doi | 10.1002/ejoc.201201198 | - |
dc.subject.wos | Science & Technology | por |
sdum.journal | European Journal of Organic Chemistry | por |
Aparece nas coleções: | CDF - FAMO - Artigos/Papers (with refereeing) CDQuim - Artigos (Papers) |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
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2012-Eur. J. Org. Chem.pdf | 1,85 MB | Adobe PDF | Ver/Abrir |