QUISQUALIC ACID

QUISQUALIC ACID Basic information
Product Name:QUISQUALIC ACID
Synonyms:3-(3,5-DIOXO-1,2,4-OXADIAZOLIDIN-2-YL)-L-ALANINE;L(+)-QUISQUALIC ACID;L-QUISQUALIC ACID;L-(+)-A-AMINO-3,5-DIOXO-1,2,4-OXADIAZOLIDINE-2-PROPANOIC ACID;(L)-(+)-ALPHA-AMINO-3,5-DIOXO-1,2,4-OXADIAZOLIDINE-2-PROPANOIC ACID;BETA-[3,5-DIOXO-1,2,4-OXADIAZOLIDIN-2-YL]-L-ALANINE;BETA-(3,5-DIOXO-1,2,4-OXADIZOLIDIN-2-YL)-L-ALANINE;(+)-QUISQUALIC ACID
CAS:52809-07-1
MF:C5H7N3O5
MW:189.13
EINECS:
Product Categories:Heterocycles;Glutamate;Amino Acids 13C, 2H, 15N;Amino Acids & Derivatives;Neurochemicals;Glutamate receptor
Mol File:52809-07-1.mol
QUISQUALIC ACID Structure
QUISQUALIC ACID Chemical Properties
Melting point 185-187°C dec.
alpha D20 +17.0° (c = 2.0 in 6M HCl)
Boiling point 324.36°C (rough estimate)
density 1.6649 (rough estimate)
refractive index 1.6190 (estimate)
storage temp. 2-8°C
solubility NH4OH 1 M: 20 mg/mL, clear, colorless
form powder
pka2.12±0.10(Predicted)
color white to off-white
Water Solubility Soluble in ethanol, water. Insoluble in organic solvents.
Merck 13,8177
BRN 1078734
Stability:Stable. Incompatible with strong oxidizing agents.
Safety Information
Hazard Codes Xn
Risk Statements 20/21/22
Safety Statements 26-36
WGK Germany 3
10
MSDS Information
ProviderLanguage
SigmaAldrich English
QUISQUALIC ACID Usage And Synthesis
DescriptionL-Quisqualic acid is a natural analog of glutamate that acts as an agonist at AMPA-selective and metabotropic glutamate receptors (EC50s = 170, 10, 40, and 29 nM at GluR-A, mGluR1, mGluR3, and mGluR5, respectively), as well as the ionotropic kainate receptor (GRIK4; Ki = 6.43 nM). L-Quisqualic acid is used to study receptor dynamics and as an excitotoxin to selectively destroy neurons in the brain or spinal cord.
Chemical PropertiesOff-White Solid
UsesAn amino acid that is able to function as an agonist at multiple excitatory amino acid receptor substrates in the central nervous system. It also has high affinity for the kainate, AMPA and the metabotropic receptors. Inhibits the Ca2+/Cl-dependent glutamic acid uptake system in brain synaptic plasma membrane preparations.
UsesQuisqualic acid has been used to test ligand-gated receptors in spiral ganglion neurons.
UsesQuisqualic acid is used to differentiate between mGluR-1 and mGluR-4. L-Quisqualic acid is an activator of GluR.
DefinitionChEBI: Quisqualic acid is a non-proteinogenic alpha-amino acid.
General DescriptionQuisqualate/ Quisqualic acid is obtained from the fruits and seeds of Quisqualis chinensis. It is an agonist at two subsets of excitatory amino acid receptors metabotropic receptors that indirectly mediate calcium mobilization from intracellular stores and, ionotropic receptors that directly control membrane channels. L-quisqualic acid is an agonist of the neurotransmitter L-glutamate.
Biological ActivityGlutamate receptor agonist acting at AMPA receptors and metabotropic glutamate receptors positively linked to phosphoinositide hydrolysis. Sensitizes neurons in hippocampus to depolarization by L-AP6 (the so called 'quis' effect). Also available as part of the Group I mGlu Receptor Tocriset™ .
Biochem/physiol ActionsActive enantiomer of quisqualic acid; excitatory amino acid at glutamate receptors.
storageStore at RT
Purification MethodsIt has been purified by ion-exchange chromatography on Dowex 50W (x 8, H+ form); the desired fractions are lyophilised and recrystallised from H2O/EtOH. It has IR (KBr) : 3400-2750br, 1830s, 1775s, 1745s and 1605s cm-1;maxand 1H NMR (NaOD/D2O, pH 13) : 3.55-3.57 (1H m, X of ABX, H-2), 3.72-3.85 (2H, AB of ABX, H-3), 1 3C NMR (D2O) : 50.1t, 53.4d, 154.8s, 159.7s and 171.3s. [Baldwin et al. J Chem Soc, Chem Commun 256 1985.] It is a quasiqualate receptor agonist [Joels et al. Proc Natl Acad Sci USA 86 3404 1989].
QUISQUALIC ACID Preparation Products And Raw materials
IBOTENIC ACID L-AP4 AIDA 4-Phosphonophenylglycine MPPG (+-)-2-AMINO-3-PHOSPHONOPROPIONIC ACID ( AP-3)NMDA ANTAGONIST 1-Hydroxy-3-methylurea [3H]QUISQUALIC ACID 2,3-Diaminopropionic acid 1,2,4-OXADIAZOLIDINE-3,5-DIONE Albizziin 3-(N-Methylamino)-L-alanine 3-UREIDOPROPIONIC ACID 2-(2-AMINO-ETHYL)-[1,2,4]OXADIAZOLIDINE-3,5-DIONE ALPHA-BENZYLQUISQUALIC ACID Hydroxyurea QUISQUALIC ACID L-2,3-Diaminopropionic acid

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