New photoremovable protecting groups for carboxylic acids with high photolytic efficiencies at near-UV irradiation. Application to the photocontrolled release of L-glutamate.

@article{Specht2006NewPP,
  title={New photoremovable protecting groups for carboxylic acids with high photolytic efficiencies at near-UV irradiation. Application to the photocontrolled release of L-glutamate.},
  author={Alexandre Specht and Jean-S{\'e}bastien Thomann and Karine Alarcon and Weerawut Wittayanan and David Ogden and Toshiaki Furuta and Yuji Kurakawa and Maurice Goeldner},
  journal={Chembiochem : a European journal of chemical biology},
  year={2006},
  volume={7 11},
  pages={1690-5}
}
We report here the syntheses and the photolytic properties of 3-(4,5-dimethoxy-2-nitrophenyl)-2-butyl (DMNPB) esters as new photoremovable groups for carboxylic acids, and their use for the caging of L-glutamate. A high-yielding synthesis of the DMNPB esters led to a 4:1 threo/erythro diastereomeric mixture, which could be separated by HPLC. While these esters were stable in neutral buffer, photolysis at 364 nm induced a > or =95 % release of the carboxylic acid, with a 0.26 quantum yield for L… CONTINUE READING