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C4147

γ-Carboxy-L-glutamic acid

Name: γ-Carboxy-<SC>L</SC>-glutamic acid
Brand: SIGMA

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About This Item

Fórmula empírica (notación de Hill):

C₆H₉NO₆

Número de CAS:

53861-57-7

Peso molecular:

191.14

Beilstein/REAXYS Number:

2417114

EC Number:

258-825-9

MDL number:

MFCD00011673

UNSPSC Code:

12352200

PubChem Substance ID:

24892669

storage temp.

−20°C

SMILES string

N[C@@H](CC(C(O)=O)C(O)=O)C(O)=O

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

InChI key

UHBYWPGGCSDKFX-VKHMYHEASA-N

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Therapeutic potential of group III metabotropic glutamate receptors.

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

Glutamate metabotropic receptors as targets for drug therapy in epilepsy.

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

Comparative effect of L-CCG-I, DCG-IV and gamma-carboxy-L-glutamate on all cloned metabotropic glutamate receptor subtypes.

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

Group II and group III metabotropic glutamate receptor agonists depress synaptic transmission in the rat spinal cord dorsal horn.

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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