Photoactivation of butyric acid from 6-aminobenzocoumarin cages


Autoria(s): Soares, Ana M. S.; Hungerford, Graham; Costa, Susana P. G.; Gonçalves, M. Sameiro T.
Data(s)

01/07/2015

Resumo

A new benzocoumarin bearing an amino group is proposed as a photocleavable protecting group for carboxylic acids. The novel heterocycle, 6-amino-4-chloromethyl-2-oxo-2H-naphtho[1,2-b]pyran was used in the preparation of ester conjugates of butyric acid, and of the corresponding mono- and di-methylated or ethylated derivatives. The photolability of the ester conjugates was studied by irradiation at selected wavelengths in methanol/HEPES buffer (80:20) solutions, and the release of butyric acid was followed with HPLC/UV and 1H NMR monitoring. Release of the carboxylic acid was faster for the monoalkylated derivatives (approximately within 20 min), at the longer wavelengths of irradiation (350 and 419 nm). The photophysics of the heterocyclic conjugates was also evaluated by both steady state and time-resolved methods.

Fundação para a Ciência e Tecnologia (FCT)

Thanks are due to the Fundação para a Ciência e Tecnologia (FCT, Portugal) for financial support to the NMR portuguese network (PTNMR, Bruker Avance III 400- Univ. Minho), FCT and FEDER (European Fund for Regional Development)- COMPETE-QREN-EU for financial support to the research centre CQ/UM [PEst[C/QUI/UI0686/2013 (FCOMP-01-0124-FEDER-022716)] and a PhD grant to A.M.S.S. (SFRH/BD/80813/2011) is also acknowledged.

Identificador

A. M. S. Soares, G. Hungerford, S. P. G. Costa, M. S. T. Gonçalves, Eur. J. Org. Chem., 2015, 5979-5986.

1099-0690

http://hdl.handle.net/1822/39215

10.1002/ejoc.201500396

Idioma(s)

eng

Publicador

Wiley-VCH

Relação

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

http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201500396/epdf

Direitos

info:eu-repo/semantics/restrictedAccess

Palavras-Chave #Coumarins #Butyric acid #Photolabile protecting groups #Fluorescence
Tipo

info:eu-repo/semantics/article