C4147
γ-Carboxy-L-glutamic acid
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About This Item
Empirical Formula (Hill Notation):
C6H9NO6
CAS Number:
Molecular Weight:
191.14
EC Number:
258-825-9
UNSPSC Code:
12352200
PubChem Substance ID:
Beilstein/REAXYS Number:
2417114
MDL number:
InChI key
UHBYWPGGCSDKFX-VKHMYHEASA-N
InChI
1S/C6H9NO6/c7-3(6(12)13)1-2(4(8)9)5(10)11/h2-3H,1,7H2,(H,8,9)(H,10,11)(H,12,13)/t3-/m0/s1
SMILES string
N[C@@H](CC(C(O)=O)C(O)=O)C(O)=O
storage temp.
−20°C
Gene Information
rat ... Grm2(24415)
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Biochem/physiol Actions
Gamma-carboxy-L-glutamic acid (GLA) is used as a metabotropic glutamate receptor (mGluR) subtype ligand wherein GLA is a group-II mGlu2 receptor and group-III mGlu7, mGlu8 antagonist and group-III mGlu4, mGlu6 agonist.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Hilde Lavreysen et al.
Current medicinal chemistry, 15(7), 671-684 (2008-03-14)
Metabotropic glutamate (mGlu) receptors have received much attention, driven by a strong belief in the potential of these modulatory glutamate receptors as drug targets. So far, major drug discovery programs have largely focused on group I (mGlu1 and 5) and
I Brabet et al.
Neuropharmacology, 37(8), 1043-1051 (1998-12-02)
In a previous study we reported that the addition of a carboxylic group to the mGlu receptor agonist aminocyclopentane-1,3-dicarboxylate (ACPD) changes its properties from agonist to antagonist at both mGlu1 and mGlu2 receptors, and resulted in an increase in affinity
Randal X Moldrich et al.
European journal of pharmacology, 476(1-2), 3-16 (2003-09-13)
Metabotropic glutamate (mGlu) receptors have multiple actions on neuronal excitability through G-protein-linked modifications of enzymes and ion channels. They act presynaptically to modify glutamatergic and gamma-aminobutyric acid (GABA)-ergic transmission and can contribute to long-term changes in synaptic function. The recent
G Gerber et al.
Neuroscience, 100(2), 393-406 (2000-09-29)
The effects of group II and group III metabotropic glutamate receptor agonists on synaptic responses evoked by primary afferent stimulation in the dorsal horn, but mostly substantia gelatinosa, neurons were studied in the spinal cord slice preparation using conventional intracellular
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