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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:
117857-95-1
Molecular Weight:
159.14
MDL number:
MFCD00210186
UNSPSC Code:
12352209
PubChem Substance ID:
329774918
NACRES:
NA.22
Pricing and availability is not currently available.

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
090K1712

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Joanna M Wierońska et al.
Pharmacological reports : PR, 57(6), 734-743 (2005-12-31)
Several lines of evidence indicate that activation of group II and III metabotropic glutamate (mGlu) receptors produces anxiolytic-like effects in rodents. On the other hand neuropeptide Y (NPY) induces an anxiolytic effect in rats after intraventricular or intraamygdalar administration. Therefore
Michael Meredith et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 24(25), 5719-5725 (2004-06-25)
Chemosignals related to reproductive and social status (pheromones) carry messages between opposite-sex and same-sex individuals in many species. Each individual must distinguish signals relevant to its own social behavior with conspecifics from signals used by other (heterospecific) species relevant to
Chew L Lau et al.
Neurochemical research, 35(5), 735-742 (2010-02-10)
Astrocytic excitatory amino acid transporters (EAATs) regulate excitatory transmission and limit excitotoxicity. Evidence for a functional interface between EAATs and glial fibrillary acidic protein (GFAP) relevant to astrocytic morphology led to investigations of actions of transportable (D-Aspartate (D-Asp) and (2S,3S,4R)-2-(carboxycyclopropyl)glycine
Christopher M Nolte et al.
Physiology & behavior, 86(3), 314-323 (2005-10-12)
The accessory olfactory bulb normally receives chemosensory input from the vomeronasal organ. Input from accessory bulb to medial amygdala for natural pheromone-containing conspecific chemosignals activates both anterior and posterior medial amygdala and elicits or modulates reproductive and social behavior. Here
Y Tan et al.
Cellular and molecular neurobiology, 26(4-6), 915-924 (2006-08-10)
1. The effects of three metabotropic glutamate receptor (mGluR) agonists were tested in two pathways of rat piriform cortex. The group I, II and III mGluR agonists used were RS-3,5-dihydroxyphenenylglycine (DHPG) (10-100 microM), (2S,1'S,2'S)-2-Carboxycyclopropyl (L-CCG) (20-100 microM) and L(+)-2-amino-4-phosphonobutyric acid
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