title: Caged glutamates with π-extended 1,2-dihydronaphthalene chromophore: design, synthesis, two-photon absorption property, and photochemical reactivity.
abstract: 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.
authors.affiliation: Department of Chemistry, Graduate School of Science, Hiroshima University (HIRODAI) , 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan.
authors.forename: Srikanth
authors.initials: S
authors.lastname: Boinapally
authors.forename: Bo
authors.initials: B
authors.lastname: Huang
authors.forename: Manabu
authors.initials: M
authors.lastname: Abe
authors.forename: Claudine
authors.initials: C
authors.lastname: Katan
authors.forename: Jun
authors.initials: J
authors.lastname: Noguchi
authors.forename: Satoshi
authors.initials: S
authors.lastname: Watanabe
authors.forename: Haruo
authors.initials: H
authors.lastname: Kasai
authors.forename: Bing
authors.initials: B
authors.lastname: Xue
authors.forename: Takayoshi
authors.initials: T
authors.lastname: Kobayashi
mesh_terms: D000586:Amination; D003374:Coumarins / Q000737:chemistry*; D005971:Glutamates / Q000138:chemical synthesis* / Q000737:chemistry*; D009281:Naphthalenes / Q000737:chemistry*; D018377:Neurotransmitter Agents / Q000138:chemical synthesis* / Q000737:chemistry; D055668:Photochemical Processes; D017785:Photons
chemical_list: D003374:Coumarins; D005971:Glutamates; D009281:Naphthalenes; D018377:Neurotransmitter Agents; C086079:1,2-dihydronaphthalene