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Merck
CN

C195

(2S,3R,4S)-α-(Carboxycyclopropyl)glycine

solid

Synonym(s):

(2S,1′R,2′S)-2-(2-Carboxycyclopropyl)glycine, (2S,3R,4S)-CCG, L-CCG-IV

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About This Item

Empirical Formula (Hill Notation):
C6H9NO4
CAS Number:
117857-95-1
Molecular Weight:
159.14
NACRES:
NA.22
PubChem Substance ID:
329774918
UNSPSC Code:
12352209
MDL number:
MFCD00210186

Key Documents

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InChI

1S/C6H9NO4/c7-4(6(10)11)2-1-3(2)5(8)9/h2-4H,1,7H2,(H,8,9)(H,10,11)/t2-,3+,4+/m1/s1

SMILES string

[H][C@]1(C[C@@H]1C(O)=O)[C@H](N)C(O)=O

InChI key

GZOVEPYOCJWRFC-UZBSEBFBSA-N

form

solid

optical activity

[α]/D +69.5°, c = 0.4 in H2O(lit.)

reaction suitability

reaction type: solution phase peptide synthesis

color

off-white

solubility

H2O: soluble

application(s)

peptide synthesis

Related Categories

Biochem/physiol Actions

Potent NMDA receptor agonist.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
090K1712

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Jennifer A Feeley Kearney et al.
Experimental neurology, 184 Suppl 1, S30-S36 (2003-11-05)
Metabotropic glutamate receptors (mGluRs) are G-protein-coupled excitatory amino acid (glutamate) receptors and are abundantly expressed in basal ganglia nuclei. We used behavioral, regional glucose uptake metabolic mapping, and FOS protein expression to examine the effects of stimulating striatal and subthalamic
Ke-Zhong Shen et al.
The Journal of physiology, 553(Pt 2), 489-496 (2003-09-23)
Patch pipettes were used to record currents in whole-cell configuration to study the effects of group II metabotropic glutamate receptor (mGluR) stimulation on synaptic transmission in slices of rat subthalamic nucleus. Evoked glutamatergic excitatory postsynaptic currents (EPSCs) were reversibly reduced
Cynthia Levinthal et al.
Pharmacology, 83(2), 88-94 (2008-12-10)
Protons act as neuromodulators and produce significant effects on synaptic transmission. The molecular basis of neuromodulation by extracellular protons is partially explained by their effects on certain neurotransmitter receptors and ion channels. The metabotropic glutamate receptors (mGluRs) are a family
Timo Kirschstein et al.
Neuropharmacology, 47(2), 157-162 (2004-06-30)
Specific agonists of metabotropic glutamate receptors (mGluRs) provide powerful tools to discriminate afferent fibers originating from different presynaptic neurons. The group II mGluR agonists L-CCG-I ((2S,1'S,2'S)-2-(2-carboxycyclopropyl)glycine) and DCG-IV ((2S,2'R,3'R)-2-(2',3'-dicarboxy-cyclopropyl)glycine) are commonly used to distinguish between mossy fiber and associational-commissural (A/C)
M Llansola et al.
Neuroscience, 133(1), 185-191 (2005-05-17)
Hyperammonemia impairs signal transduction associated to glutamate receptors and phosphorylation of some neuronal proteins including microtubule-associated protein 2 (MAP-2). The aim of this work was to analyze the effects of hyperammonemia on modulation of MAP-2 phosphorylation by metabotropic glutamate receptors
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