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Key Documents

C195

Sigma-Aldrich

(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:
Molecular Weight:
159.14
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.22

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

SMILES string

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

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

InChI key

GZOVEPYOCJWRFC-UZBSEBFBSA-N

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Biochem/physiol Actions

Potent NMDA receptor agonist.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
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
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
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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