Utilize este identificador para referenciar este registo: http://hdl.handle.net/1822/48099

TítuloSynthesis and preliminary biological evaluation of new phenolic and catecholic dehydroamino acid derivatives
Autor(es)Monteiro, Luís S.
Oliveira, Sandra
Paiva-Martins, Fátima
Ferreira, Paula M. T.
Pereira, David M.
Andrade, Paula B.
Valentão, P.
Dehydroamino acids
Cell viability studies
CitaçãoLuís S. Monteiro, Sandra Oliveira, Fátima Paiva-Martins, Paula M.T. Ferreira, David M. Pereira, Paula B. Andrade, Patrícia Valentão, Tetrahedron 73 (2017) 6199e6209
Resumo(s)A library of N-phenolic and N-catecholic dehydroamino acid derivatives was prepared using an innovative synthetic strategy that involves mild reaction conditions and simple work-up procedures. The method comprises coupling of phenolic or catecholic acids with β-hydroxyamino acids followed by tert-butyloxycarbonylation of all hydroxyl groups using tert-butyldicarbonate and 4-dimethylaminopyridine as catalyst. Treatment of these amino acids with N,N,N’,N’-tetramethylguanidine affords the corresponding O-tert-butyloxycarbonyldehydro-amino acid derivative. Deprotection of the aromatic hydroxyl groups is carried out with trifluoroacetic acid. This synthetic strategy can be applied in a one-pot procedure and yields compounds that can be easily inserted into peptides or other biomolecules after cleavage of the C-protecting group. Preliminary studies of cell viability show that these new compounds display very low or no toxicity. These dehydroamino acids with a phenolic or catecholic moiety can have intrinsic biological activity or used to prepare new hydrogels that mimic mussel adhesive proteins.
Arbitragem científicayes
Aparece nas coleções:CDQuim - Artigos (Papers)

Ficheiros deste registo:
Ficheiro Descrição TamanhoFormato 
2017-Tetrahedron I.pdf740,89 kBAdobe PDFVer/Abrir

Partilhe no FacebookPartilhe no TwitterPartilhe no DeliciousPartilhe no LinkedInPartilhe no DiggAdicionar ao Google BookmarksPartilhe no MySpacePartilhe no Orkut
Exporte no formato BibTex mendeley Exporte no formato Endnote Adicione ao seu Currículo DeGóis