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https://hdl.handle.net/1822/48099
Título: | Synthesis 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. |
Palavras-chave: | Catechol Dehydroamino acids tert-Butyloxycarbonylation Dehydration Cell viability studies |
Data: | 14-Set-2017 |
Editora: | Elsevier 1 |
Revista: | Tetrahedron |
Citação: | Luís 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. |
Tipo: | Artigo |
URI: | https://hdl.handle.net/1822/48099 |
DOI: | 10.1016/j.tet.2017.09.012 |
ISSN: | 0040-4020 |
Arbitragem científica: | yes |
Acesso: | Acesso aberto |
Aparece nas coleções: | CDQuim - Artigos (Papers) |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
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2017-Tetrahedron I.pdf | 740,89 kB | Adobe PDF | Ver/Abrir |