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| - An Antenna-Sensitized Nitroindoline Precursor to EnablePhotorelease of l-Glutamate in High Concentrations
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| - 1-Acyl-7-nitroindolines are useful reagents for rapid release of carboxylates upon flash photolysisin aqueous solution and have been particularly effective for rapid (submicrosecond) release ofneuroactive amino acids such as l-glutamate in biological experiments. In model systems theefficiency of photorelease has been shown to be greatly improved by attachment of a benzophenonetriplet-sensitizing antenna. The present work describes synthesis and initial biological evaluationof the l-glutamate precursor 3. A significant improvement in the overall synthesis uses double Bocprotection of the glutamate amino group to avoid side reactions during introduction of the nitrogroup. To accommodate the multiple functionalities in 3, linkage of the nitroindoline andbenzophenone moieties is carried out late in the synthesis. Photolysis of 3 occurs with near-quantitative stoichiometry and the released l-glutamate efficiently activates neuronal glutamateion channels.
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