CID 6971145

Base Information

• Chemical Name: CID 6971145
• CAS No.: 52809-07-1
• Molecular Formula: C5H7N3O5
• Molecular Weight: 189.128
• Hs Code.: 2934999090
• Mol file: 52809-07-1.mol

Synonyms:2jbk;2or4;3fee

Chemical Property of CID 6971145

Chemical Property:

• Appearance/Colour: off-white solid
• Melting Point: 185-187 °C
• Refractive Index: 1.571
• Boiling Point: 324.36°C (rough estimate)
• PKA: 2.12±0.10(Predicted)
• PSA: 131.32000
• Density: 1.679 g/cm³
• LogP: -1.75820
• Storage Temp.: 2-8°C
• Solubility.: NH4OH 1 M: 20 mg/mL, clear, colorless
• Water Solubility.: Soluble in ethanol, water. Insoluble in organic solvents.
• XLogP3: -3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 189.03857033
• Heavy Atom Count: 13
• Complexity: 259

Purity/Quality:

≥97% ^*data from raw suppliers

L-Quisqualic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C(C(=O)[O-])[NH3+])N1C(=O)NC(=O)O1
• Isomeric SMILES: C([C@@H](C(=O)[O-])[NH3+])N1C(=O)NC(=O)O1
• Description: L-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.
• Uses: An 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. Quisqualic acid has been used to test ligand-gated receptors in spiral ganglion neurons. Quisqualic acid is used to differentiate between mGluR-1 and mGluR-4. L-Quisqualic acid is an activator of GluR.

Technology Process of CID 6971145

There total 7 articles about CID 6971145 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 10.0%

O-acetyl-L-serine (5147-00-2,25248-96-8,44901-25-9) + [1,2,4]oxadiazolidine-3,5-dione (24603-68-7) → quisqualic acid (52809-07-1)

Guidance literature:

With gallium(III) nitrate; pyridoxal 5'-phosphate; In water; at 62 - 65 ℃; for 2h; pH=5.0;

Reference yield:

(S)-2-tert-Butoxycarbonylamino-3-(3,5-dioxo-[1,2,4]oxadiazolidin-2-yl)-propionic acid tert-butyl ester → quisqualic acid (52809-07-1)

Guidance literature:

With Amberlite IR-45; methoxybenzene; trifluoroacetic acid; In N,N-dimethyl-formamide; at 0 ℃; for 16h; Yield given;

DOI:10.1016/0040-4039(96)01061-1

Reference yield:

L-Cysteine (52-90-4) + [1,2,4]oxadiazolidine-3,5-dione (24603-68-7) → quisqualic acid (52809-07-1)

Guidance literature:

With Tris-HCl buffer; at 30 ℃; for 0.166667h; β-cyano-L-alanine synthase (from Spinacia oleracea, Chenopodiaceae);

DOI:10.1016/0031-9422(88)80087-6

upstream raw materials:

L-serin

[1,2,4]oxadiazolidine-3,5-dione

L-Cysteine

O-acetyl-L-serine

Downstream raw materials:

L-2-Amino-3-ureido-propanoic acid

Refernces

• 1、 Ikegami, Fumio,Komada, Yumiko,Kobori, Masuko,Hawkins, Douglas R.,Murakoshi, Isamu. "BIOSYNTHESIS OF β-(1,2,4-TRIAZOL-1-YL)ALANINE IN HIGHER PLANTS". . p. 2507 - 2508. Retrieved 2007/10/02.
• 2、 Murakoshi, Isamu,Ikegami, Fumio,Yoneda, Yoshihiro,Ihara, Harumi,Sakata, Kumiko,Koide, Chiharu. "Biomimetic Synyhesis of Heterocyclic β-Substituted Alanines by Pyridoxal 5'-Phosphate-Catalyzed Chemical Reactions". . p. 1473 - 1478. Retrieved 2007/10/02.