Photorelease of amino acids from novel thioxobenzo[f]benzopyran ester conjugates |
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Authors: | Ana M Piloto Ana M S Soares Susana P G Costa M Sameiro T Gon?alves |
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Institution: | 1. Centro de Química, Universidade do Minho, Campus de Gualtar, 4710-057, Braga, Portugal
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Abstract: | Aiming at the enhancement of the performance of (9-methoxy-3-oxo-3H-benzof]benzopyran-1-yl) methyl ester as photocleavable protecting group for the carboxylic acid function at long-wavelengths, 9-methoxy-3-thioxo-3H-benzof]benzopyran-l-valine and l-phenylalanine model conjugates were prepared through a thionation reaction of the corresponding oxo-benzobenzopyrans. These thioxobenzobenzopyran derivatives were subjected to photocleavage reactions in the same conditions as the parent oxo-benzobenzopyrans at different wavelengths of irradiation, and photocleavage data were obtained. It was found that the exchange of the carbonyl by a thiocarbonyl group enhanced the performance of the heterocyclic protecting group at 419?nm by improving the photolysis rates, making it an appropriate group for practical applications at long wavelengths. |
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