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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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Chao-Yin Chen et al.
The Journal of physiology, 562(Pt 2), 535-551 (2004-11-13)
The nucleus tractus solitarii (NTS) is essential for coordinating arterial baroreflex control of blood pressure. The primary baroreceptor afferent fibres make their first excitatory synaptic contact at second-order NTS neurones with glutamate as the major neurotransmitter. Glutamate regulates its own
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
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
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
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
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