Caged Glutamates with 蟺-Extended 1,2-Dihydronaphthalene Chromophore: Design, Synthesis, Two-Photon Absorption Property, and Photochemical Reactivity

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• 作者：Srikanth Boinapally ; Bo Huang ; Manabu Abe ; Claudine Katan ; Jun Noguchi ; Satoshi Watanabe ; Haruo Kasai ; Bing Xue ; Takayoshi Kobayashi
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：September 5, 2014
• 年：2014
• 卷：79
• 期：17
• 页码：7822-7830
• 全文大小：539K
• ISSN：1520-6904

文摘

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 蟺-extended 1,2-dihydronaphthalene structures, which possess a two-photon cross-section of 鈭?20 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鈥揗iyaura cross-coupling and Buchwald鈥揌artwig amination were used as the key reactions to synthesize the caged compounds.