期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 79, 期 17, 页码 7822-7830出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo501425p
关键词
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资金
- Ministry of Education, Culture, Sports, Science and Technology, Japan [24109008, 21108516, 19350021]
- Tokuyama Science Foundation
- Grants-in-Aid for Scientific Research [26250004, 26111706, 21000009, 26430005] Funding Source: KAKEN
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 pi-extended 1,2-dihydronaphthalene structures, which possess a two-photon cross-section of similar to 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.
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