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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: Specht A, Thomann JS, Alarcon K, Wittayanan W, Ogden D, Furuta T, Kurakawa Y, Goeldner M. Journal: Chembiochem; 2006 Nov; 7(11):1690-5. PubMed ID: 16991166. Abstract: 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-glutamate formation. L-Glutamate release was also possible by two-photon photolysis with an action cross section of 0.17 GM at 720 nm. Laser photolysis at 350 nm generated a transient species at around 410 nm, attributed to a quinonoid aci-nitro intermediate that decayed in the submillisecond time range (t(1/2)=0.53 ms) for the faster gamma-L-glutamyl threo-esters. Given the absorbance of these esters (lambda(max)=350 nm; epsilon=4500), the threo DMNPB esters represent new caging groups that can be efficiently photolyzed at near-UV wavelengths. An efficient and rapid photolytic release of L-glutamate has been demonstrated on hippocampal neurons in primary culture.[Abstract] [Full Text] [Related] [New Search]