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|Synthesis and preliminary biological evaluation of new phenolic and catecholic dehydroamino acid derivatives
|Monteiro, Luís S.
Ferreira, Paula M. T.
Pereira, David M.
Andrade, Paula B.
Cell viability studies
|Luís S. Monteiro, Sandra Oliveira, Fátima Paiva-Martins, Paula M.T. Ferreira, David M. Pereira, Paula B. Andrade, Patrícia Valentão, Tetrahedron 73 (2017) 6199e6209
|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.
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