Please use this identifier to cite or link to this item: http://hdl.handle.net/1822/11744

TitleA mild high yielding synthesis of oxazole-4-carboxylate derivatives
Author(s)Ferreira, Paula M. T.
Castanheira, Elisabete M. S.
Monteiro, Luís S.
Pereira, Goreti
Vilaça, Helena
KeywordsN-Acyl-threonine derivatives
N-Acyl-b-halodehydroaminobutyric acids
Oxazole-4-carboxylates
Fluorescent probes
Labelled peptides
N-Acyl-β-halodehydroaminobutyric acids
Issue dateDec-2010
PublisherElsevier
JournalTetrahedron
Citation"Tetrahedron". ISSN 0040-4020. 66 (2010) 8672-8680.
Abstract(s)Several 2,5-disubstituted oxazole-4-carboxylates were prepared in high yields from the methyl esters of N-acyl-b-halodehydroaminobutyric acid derivatives by treatment with a 2% solution of DBU in acetonitrile. The scope of this reaction was investigated and it was found that dehydrodipeptides having a b-bromodehydroaminobutyric acid residue gave the corresponding oxazoles in good yields. The photophysical properties of some of the oxazoles prepared were studied in four solvents of different polarity. All compounds have reasonable high fluorescence quantum yields and a moderate solvent sensitivity, which makes them good candidates to be used as fluorescent probes. One of the fluorescent oxazoles prepared was inserted after cleavage of the methyl ester into two model peptides using a conventional solution phase strategy. The photophysical properties of the labelled peptides were studied in ethanol and water and compared with those of the oxazole. The results obtained showed that the oxazole maintains a good fluorescence level and the same solvent sensitivity when linked to a peptide chain.
TypeArticle
URIhttp://hdl.handle.net/1822/11744
DOI10.1016/j.tet.2010.09.014
ISSN0040-4020
Peer-Reviewedyes
AccessRestricted access (UMinho)
Appears in Collections:CDF - FAMO - Artigos/Papers (with refereeing)

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