Photolabile protection for amino acids: studies on the release from novel benzoquinolone cages


Autoria(s): Fonseca, Andrea Susana Cabral da; Soares, Ana M. S.; Gonçalves, M. Sameiro T.; Costa, Susana P. G.
Data(s)

23/07/2015

Resumo

The synthesis of a novel fused nitrogen heterocycle, benzoquinolone, for evaluation as a photocleavable protecting group is described for the first time, by coupling to model amino acids (alanine, phenylalanine and glutamic acid). Conversion of the phenylalanine ester conjugate to the thionated derivative was accomplished by reaction with Lawesson’s reagent. Photocleavage studies of the carbonyl and thiocarbonyl benzoquinolone conjugates in various solvents and at different wavelengths (300, 350 and 419 nm) showed that the most interesting result was obtained at 419 nm for the thioconjugate, revealing that the presence of the thiocarbonyl group clearly improved the photolysis rates, giving practicable irradiations times for the release of the amino acids (less than 1 minute).

Fundação para a Ciência e Tecnologia (FCT)

Identificador

Andrea S. C. Fonseca, Ana M. S. Soares, M. Sameiro T. Gonçalves, Susana P. G. Costa, Amino Acids, 2015, 47, 2573-2582.

0939-4451

http://hdl.handle.net/1822/38793

10.1007/s00726-015-2048-4

Idioma(s)

eng

Publicador

Springer

Relação

info:eu-repo/grantAgreement/FCT/5876-PPCDTI/69607/PT

info:eu-repo/grantAgreement/FCT/COMPETE/132953/PT

http://link.springer.com/article/10.1007%2Fs00726-015-2048-4

Direitos

info:eu-repo/semantics/restrictedAccess

Palavras-Chave #Quinolone #Coumarin #Amino acids #Phototriggers #Photolabile protecting groups
Tipo

info:eu-repo/semantics/article