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Proceedings of the National Academy of Sciences of the United States of America logoLink to Proceedings of the National Academy of Sciences of the United States of America
. 1994 Sep 13;91(19):8752–8756. doi: 10.1073/pnas.91.19.8752

Photolabile precursors of glutamate: synthesis, photochemical properties, and activation of glutamate receptors on a microsecond time scale.

R Wieboldt 1, K R Gee 1, L Niu 1, D Ramesh 1, B K Carpenter 1, G P Hess 1
PMCID: PMC44684  PMID: 8090718

Abstract

Newly synthesized photolabile derivatives of glutamate, caged glutamate, that release free glutamate on a microsecond time scale after a pulse of UV laser light are described. 2-Nitrobenzyl derivatives were attached to the amino or carboxyl groups of glutamate. Substitution with a -CO2- group at the benzylic carbon accelerates the photolysis reaction when compared to -H and -CH3 substituents. gamma-O-(alpha-Carboxy-2-nitrobenzyl)glutamate is stable at neutral pH. In 100 mM phosphate buffer at pH 7.0, the compound is photolyzed at 308 nm with a quantum product yield of 0.14. The half-life of the major component of the photolytic reaction, as judged by the transient absorbance change at 430 nm, is 21 microseconds (approximately 90%); the half-life of a minor component (approximately 10%) is 0.2 ms. The amino-linked derivatives have half-lives in the millisecond region and a 4-fold lower quantum yield. The potential of the newly synthesized compound for use in rapid chemical kinetic investigations of glutamate receptors is demonstrated. (i) The caged glutamate at 1 mM concentration does not desensitize glutamate receptors in rat hippocampal neurons. (ii) Caged glutamate (1 mM) does not inhibit activation of the receptors by 50 microM glutamate. (iii) Photolysis of the compound induces rapid onset of transmembrane currents in rat hippocampal neurons.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

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