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Improved Synthesis of Caged Glutamate and Caging Each Functional Group
- Source :
- ACS Chemical Neuroscience. 9:2713-2721
- Publication Year :
- 2018
- Publisher :
- American Chemical Society (ACS), 2018.
-
Abstract
- Glutamate is an excitatory neurotransmitter that controls numerous pathways in the brain. Neuroscientists make use of photoremovable protecting groups, also known as cages, to release glutamate with precise spatial and temporal control. Various cage designs have been developed and amongst the most effective has been the nitroindolinyl caging of glutamate. We, hereby, report an improved synthesis of one of the current leading molecules of caged glutamate, 4-carboxymethoxy-5,7-dinitroindolinyl glutamate (CDNI-Glu), which possesses efficiencies with the highest reported quantum yield of at least 0.5. We present the shortest route, to date, for the synthesis of CDNI-Glu in 4 steps, with a total reaction time of 40 h and an overall yield of 20%. We also caged glutamate at the other two functional groups, thereby, introducing two new cage designs: α-CDNI-Glu and N-CDNI-Glu. We included a study of their photocleavage properties using UV-vis, NMR, as well as a physiology experiment of a two-photon uncaging of CDNI-Glu in acute hippocampal brain slices. The newly introduced cage designs may have the potential to minimize the interference that CDNI-Glu has with the GABA(A) receptor. We are broadly disseminating this to enable neuroscientists to use these photoactivatable tools.
- Subjects :
- 0301 basic medicine
Indoles
Magnetic Resonance Spectroscopy
Patch-Clamp Techniques
Physiology
Cognitive Neuroscience
Glutamic Acid
Caged glutamate
Hippocampus
Biochemistry
Article
Excitatory neurotransmitter
Mice
03 medical and health sciences
chemistry.chemical_compound
0302 clinical medicine
Glutamates
Animals
GABA-A Receptor Antagonists
Photons
Photolysis
Glutamate receptor
Cell Biology
General Medicine
Receptors, GABA-A
030104 developmental biology
chemistry
Yield (chemistry)
Functional group
Biophysics
030217 neurology & neurosurgery
Subjects
Details
- ISSN :
- 19487193
- Volume :
- 9
- Database :
- OpenAIRE
- Journal :
- ACS Chemical Neuroscience
- Accession number :
- edsair.doi.dedup.....5632bacb5c3633eeb04b1a0fe662ad5f