Synthesis and preliminary biological evaluation of new phenolic and catecholic dehydroamino acid derivatives

• Tipo: Artigo em Revista Científica Internacional
• Data: 2017

Autores

Monteiro, LS (Autor) Outra; Oliveira, S (Autor) Outra; Fatima Paiva Martins (Autor) FCUP; Ferreira, PMT (Autor) Outra; David M Pereira (Autor) FFUP; Paula B Andrade (Autor) FFUP; Patricia Valentao (Autor) FFUP

Revista

Título: Tetrahedron

Vol. 73

Páginas: 6199-6209

ISSN: 0040-4020

Editora: Elsevier

Indexação

ISI Web of Knowledge - 7 Citações

Scopus - 8 Citações

Outras Informações

ID Authenticus: P-00N-1PP

DOI: 10.1016/j.tet.2017.09.012

Abstract (EN): 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 beta-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-butyloxycarbonyldehydroamino 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.

Idioma: Inglês

Tipo (Avaliação Docente): Científica

Nº de páginas: 11