An antenna-sensitized nitroindoline precursor to enable photorelease of L-glutamate in high concentrations
An antenna-sensitized nitroindoline precursor to enable photorelease of L-glutamate in high concentrations
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DOI：
10.1021/jo049071x
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发表时间：
2004-10-15
影响因子：
3.6
通讯作者：
Corrie, JET
中科院分区：
文献类型：
--
作者：
Papageorgiou, G;Ogden, D;Corrie, JET
1-酰基-7-硝基吲哚类化合物是水溶液中快速光解羧酸盐的有用试剂，在生物实验中对l-谷氨酸等神经活性氨基酸的快速（亚微秒）释放特别有效。在模型系统中，通过附加二苯甲酮三致敏天线可以大大提高光释放效率。本文介绍了l -谷氨酸前体3的合成和初步生物学评价。在整个合成中有一个显著的改进，使用谷氨酸氨基的双Boc保护，以避免硝基引入时的副反应。为了适应3中的多个功能，在合成后期进行硝基吲哚和二苯甲酮部分的连接。3的光解发生在接近定量的化学计量学中，释放的l -谷氨酸有效地激活神经元谷氨酸离子通道。
1-Acyl-7-nitroindolines are useful reagents for rapid release of carboxylates upon flash photolysis in aqueous solution and have been particularly effective for rapid (submicrosecond) release of neuroactive amino acids such as L-glutamate in biological experiments. In model systems the efficiency of photorelease has been shown to be greatly improved by attachment of a benzophenone triplet-sensitizing antenna. The present work describes synthesis and initial biological evaluation of the L-glutamate precursor 3. A significant improvement in the overall synthesis uses double Boc protection of the glutamate amino group to avoid side reactions during introduction of the nitro group. To accommodate the multiple functionalities in 3, linkage of the nitroindoline and benzophenone moieties is carried out late in the synthesis. Photolysis of 3 occurs with near-quantitative stoichiometry and the released L-glutamate efficiently activates neuronal glutamate ion channels.