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

• Type: Article in International Scientific Journal
• Date: 2017

Authors

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

Journal

Title: Tetrahedron

Vol. 73

Pages: 6199-6209

ISSN: 0040-4020

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 7 Citations

Scopus - 8 Citations

Other information

Authenticus ID: 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.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 11