Caged Glutamates with π-Extended 1,2-Dihydronaphthalene Chromophore: Design, Synthesis, Two-Photon Absorption Property, and Photochemical Reactivity - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2014

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

Résumé

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.
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Dates et versions

hal-01061379 , version 1 (24-11-2016)

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Srikanth Boinapally, Bo Huang, Manabu Abe, Claudine Katan, Jun Noguchi, et al.. Caged Glutamates with π-Extended 1,2-Dihydronaphthalene Chromophore: Design, Synthesis, Two-Photon Absorption Property, and Photochemical Reactivity. Journal of Organic Chemistry, 2014, 79 (17), pp.7822-7830. ⟨10.1021/jo501425p⟩. ⟨hal-01061379⟩
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