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• W2066672090 abstract "The application of the desyl or 2-oxo-1,2-diphenylethyl moiety as a photolabile ligand for the release of phosphates such as cAMP and inorganic phosphate (Pi)1,2 is extended to include selected excitatory amino acids. The synthesis and photochemical studies of N- and O-desyl-caged versions of the endogenous amino acid neurotransmitters glutamate and γ-aminobutyric acid (GABA) are reported. Photolysis at 350 nm of solutions of γ-O-desyl glutamate (11) and O-desyl GABA (14) in 1:1 H2O−acetonitrile cleanly produced free glutamate and GABA, respectively, with rate constants of ca. 107 s-1; 2-phenylbenzo[b]furan (2) was the only photobyproduct detected by HPLC. Photolysis quantum efficiencies for the disappearance of O-desyl amino acid esters were in the range of 0.29−0.31, and the appearance efficiencies of furan 2 (and the corresponding amino acid) were 0.14. The photolysis of 14 was efficiently quenched with sodium 2-naphthalenesulfonate, yielding a triplet lifetime of ca. 10 ns. Photolysis of 11 in mammalian brain tissue slices resulted in glutamate receptor activation, as indicated by whole cell electrophysiological measurements. Photolysis of the other desyl amino acids resulted in decomposition and produced several products but did not lead to the formation of furan 2." @default.
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• W2066672090 date "1996-01-01" @default.
• W2066672090 modified "2023-09-30" @default.
• W2066672090 title "Desyl Esters of Amino Acid Neurotransmitters. Phototriggers for Biologically Active Neurotransmitters" @default.
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• W2066672090 doi "https://doi.org/10.1021/jo951635x" @default.
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