Azaheterocycles as caging groups: synthesis and photolysis studies with a model carboxylic acid

Abstract

The (acridin-9-yl)methyl and (9-ethyl-9H-carbazol-3-yl)methyl groups were evaluated as photocleavable protecting groups by using butyric acid as a model carboxylic acid. Photocleavage studies of the corresponding ester conjugates were conducted in a Rayonet RPR-100 photochemical reactor in a mixture of methanol or acetonitrile with aqueous HEPES buffer (in a 80:20 proportion) at different wavelengths of irradiation. It was found that the most efficient release of butyric acid occurred from the corresponding (acridin-9-yl)methyl ester conjugate in methanol/HEPES buffer (80:20) solutions.