Boinapally Srikanth, Huang Bo, Abe Manabu, Katan Claudine, Noguchi Jun, Watanabe Satoshi, Kasai Haruo, Xue Bing, Kobayashi Takayoshi
Department of Chemistry, Graduate School of Science, Hiroshima University (HIRODAI) , 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan.
J Org Chem. 2014 Sep 5;79(17):7822-30. doi: 10.1021/jo501425p. Epub 2014 Aug 13.
Caging and photochemical uncaging of the excitatory neurotransmitter l-glutamate (glu) offers a potentially valuable tool for understanding the mechanisms of neuronal processes. Designing water-soluble caged glutamates with the appropriate two-photon absorption property is an attractive strategy to achieve this. This paper describes the design, synthesis, and photochemical reactivity of caged glutamates with π-extended 1,2-dihydronaphthalene structures, which possess a two-photon cross-section of ∼120 GM and an excellent buffer solubility (up to 115 mM). High yields up to 99% glutamate were observed in the photolysis of two caged glutamates. Suzuki-Miyaura cross-coupling and Buchwald-Hartwig amination were used as the key reactions to synthesize the caged compounds.
对兴奋性神经递质L-谷氨酸（glu）进行笼化和光化学解笼化，为理解神经元过程的机制提供了一种潜在的有价值工具。设计具有合适双光子吸收特性的水溶性笼化谷氨酸是实现这一目标的一种有吸引力的策略。本文描述了具有π-扩展1,2-二氢萘结构的笼化谷氨酸的设计、合成和光化学反应性，其双光子截面约为120 GM，缓冲溶解度极佳（高达115 mM）。在两种笼化谷氨酸的光解过程中观察到高达99%的谷氨酸高产率。铃木-宫浦交叉偶联反应和布赫瓦尔德-哈特维希胺化反应被用作合成笼化化合物的关键反应。
