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Development of the 8-aza-3-bromo-7-hydroxycoumarin-4-ylmethyl group as a new entry of photolabile protecting groups
Authors:Hikaru Takano  Tetsuo Narumi  Nami Ohashi  Akinobu Suzuki  Toshiaki Furuta  Wataru Nomura  Hirokazu Tamamura
Institution:1. Institution of Biomaterial and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kandasurugadai, Chiyoda-ku, Tokyo 101-0062, Japan;2. Department of Biomolecular Science, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan
Abstract:A significant substitution effect of the position of the bromo group on the photosensitivity of the 8-azacoumarin chromophore leads to the development of a highly photosensitive 8-aza-3-bromo-7-hydroxycoumarin-4-ylmethyl (aza-3-Bhc) group that shows excellent photolytic efficiency and hydrophilicity with long-wavelength absorption maxima. The newly identified aza-3-Bhc group can be applied to caged glutamates for ester-type and carbamate-type protections of carboxyl and amino functionalities.
Keywords:Azacoumarin  Photolabile protecting groups  Caged compounds  Photolytic efficiency  Hydrophilicity
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