Tricholomic acid

Base Information

• Chemical Name: Tricholomic acid
• CAS No.: 2644-49-7
• Molecular Formula: C₅H₈N₂O₄
• Molecular Weight: 160.13
• Wikipedia: Tricholomic_acid
• ChEMBL ID: CHEMBL408899
• Mol file: 2644-49-7.mol

Synonyms:amino-(3'-hydroxy-4',5'-dihydroisoxazol-5'-yl)acetic acid;tricholomic acid

Chemical Property of Tricholomic acid

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 101.65000
• Density: 1.507g/cm³
• LogP: -0.75250
• XLogP3: -4.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 160.04840674
• Heavy Atom Count: 11
• Complexity: 193

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(ONC1=O)C(C(=O)O)N
• General Description: Alpha-amino-3-oxo-5-isoxazolidineacetic acid, also known as tricholomic acid or erythro-cycloglutamic acid, is a glutamate receptor agonist with stereochemistry-dependent pharmacological activity. The four enantiopure isomers of alpha-amino-3-oxo-5-isoxazolidineacetic acid exhibit distinct activity and selectivity profiles at ionotropic (iGluRs) and metabotropic (mGluRs) glutamate receptors, as demonstrated through binding assays, calcium imaging, and second messenger studies. The stereochemistry of its two chiral centers significantly influences its receptor interactions, making it a valuable tool for studying glutamate receptor subtypes.

Technology Process of Tricholomic acid

There total 6 articles about Tricholomic acid 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: 43.0%

threo-DL-N-benzyloxycarbonyl-α-amino-3-oxo-5-isoxazolidineacetic acid (80132-08-7,80132-09-8,104832-74-8) → threo-DL-tricholomic acid (2190-77-4,2644-48-6,2644-49-7,17268-06-3,23150-59-6,23150-60-9,24135-90-8,24135-91-9)

Guidance literature:

With ammonia; lithium; Heating;

DOI:10.1016/S0040-4020(01)96774-2

Reference yield:

α-ketoglutaric acid (328-50-7) → threo-DL-tricholomic acid (2190-77-4,2644-48-6,2644-49-7,17268-06-3,23150-59-6,23150-60-9,24135-90-8,24135-91-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 71 percent / 4 h / 80 °C / 10 - 15 Torr

2: 91 percent / Et₃N / ethyl acetate / 2 h / Heating

3: 99 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene (DBU) / tetrahydrofuran / 0.5 h / 0 °C

4: 1.) N-hydroxysuccinimide, N,N-dicyclohexylcarbodiimide (DCC) / 1.) THF, 2.) RT

5: 57 percent / thiophenol, Zn-Cu complex / dimethylformamide / 1 h / 65 °C

6: 86 percent / 1N NaOH / H₂O / 0.67 h / Heating

7: 43 percent / anhyd liquid ammonia, Li / Heating

With sodium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; ammonia; lithium; copper; thiophenol; triethylamine; dicyclohexyl-carbodiimide; 1,5-Diazabicyclo[5.4.0]undec-5-ene; zinc; In tetrahydrofuran; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)96774-2

Reference yield:

N-benzyloxycarbonyl-2-aminotetrahydro-5-oxo-2-furancarboxylic acid (104754-51-0) → threo-DL-tricholomic acid (2190-77-4,2644-48-6,2644-49-7,17268-06-3,23150-59-6,23150-60-9,24135-90-8,24135-91-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 91 percent / Et₃N / ethyl acetate / 2 h / Heating

2: 99 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene (DBU) / tetrahydrofuran / 0.5 h / 0 °C

3: 1.) N-hydroxysuccinimide, N,N-dicyclohexylcarbodiimide (DCC) / 1.) THF, 2.) RT

4: 57 percent / thiophenol, Zn-Cu complex / dimethylformamide / 1 h / 65 °C

5: 86 percent / 1N NaOH / H₂O / 0.67 h / Heating

6: 43 percent / anhyd liquid ammonia, Li / Heating

With sodium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; ammonia; lithium; copper; thiophenol; triethylamine; dicyclohexyl-carbodiimide; 1,5-Diazabicyclo[5.4.0]undec-5-ene; zinc; In tetrahydrofuran; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)96774-2

upstream raw materials:

threo-DL-N-benzyloxycarbonyl-α-amino-3-oxo-5-isoxazolidineacetic acid

α-ketoglutaric acid

N-benzyloxycarbonyl-2-aminotetrahydro-5-oxo-2-furancarboxylic acid

N-benzyloxycarbonyl-(Z)-α,β-dehydroglutamic-γ-hydroxamic acid

Refernces

Synthesis and pharmacological characterization at glutamate receptors of the four enantiopure isomers of tricholomic acid

10.1021/jm701394a

The research focuses on the synthesis and pharmacological characterization of the four enantiopure isomers of tricholomic acid at glutamate receptors. The study involves the synthesis of erythro- and threo-amino-(3′-hydroxy-4′,5′-dihydro-isoxazol-5′-yl)-acetic acids, which were prepared via the 1,3-dipolar cycloaddition of bromonitrile oxide to (R)- or (S)-3-(tert-butoxycarbonyl)2,2-dimethyl-4-vinyloxazolidine. The pharmacological profiles of these amino acids were evaluated to understand the relationship between their activity/selectivity and the stereochemistry of the two stereogenic centers. The experiments utilized various reactants, including dibromoformaldoxime and NaHCO3, and analytical techniques such as 1H NMR and 13C NMR spectroscopy, HPLC, and optical rotation measurements to determine the enantiomeric excess and absolute configuration of the synthesized compounds. The synthesized enantiomers were then tested for their activity at iGluRs and mGluRs using in vitro binding assays, calcium imaging assays on HEK cells expressing different iGluR subtypes, and second messenger assays on CHO cells expressing mGluR subtypes.

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