(2S)-2-[[(1S)-1-carboxy-3-methylbutyl]carbamoylamino]pentanedioic acid

Base Information

• Chemical Name: (2S)-2-[[(1S)-1-carboxy-3-methylbutyl]carbamoylamino]pentanedioic acid
• CAS No.: 723331-20-2
• Molecular Formula: C₁₂H₂₀N₂O₇
• Molecular Weight: 304.3
• ChEMBL ID: CHEMBL596351
• DSSTox Substance ID: DTXSID60471136
• Nikkaji Number: J2.054.600J
• Pharos Ligand ID: NVBYFAQB3Y7B
• Wikidata: Q76421900
• Mol file: 723331-20-2.mol

Synonyms:ZJ43

Chemical Property of (2S)-2-[[(1S)-1-carboxy-3-methylbutyl]carbamoylamino]pentanedioic acid

Chemical Property:

• PSA: 153.03000
• LogP: 0.88470
• Storage Temp.: Store at -20°C
• Solubility.: Soluble in DMSO (up to at least mg/ml) or in Water (up to at least 25 mg/ml)
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 304.12705098
• Heavy Atom Count: 21
• Complexity: 408

Purity/Quality:

98% ^*data from raw suppliers

ZJ43 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(C(=O)O)NC(=O)NC(CCC(=O)O)C(=O)O
• Isomeric SMILES: CC(C)C[C@@H](C(=O)O)NC(=O)N[C@@H](CCC(=O)O)C(=O)O
• Description: ZJ43 (723331-20-2) is potent inhibitor of glutamate carboxypeptidases II (Ki = 0.8 nM) and III (Ki = 23 nM).1?It potently (IC50?= 2.4 nM) inhibited the ability of glutamate carboxypeptidase II to hydrolyze the neurotransmitter N-acetylaspartylglutamate (NAAG) resulting in an increase in synaptic levels of group II mGluRs. Peripherally administered ZJ43 increased the activation of mGluR3 by NAAG released from peripheral sensory neurites resulting in analgesia.2,3?ZJ43 has also shown efficacy in other inflammatory pain models.4,5
• Uses: ZJ 43 is a glutamate carboxypeptidase II (GCPII) and N-acetylaspartylglutamate (NAAG) inhibitor that reduces the deleterious effects of excessive extracellular glutamate.

Technology Process of (2S)-2-[[(1S)-1-carboxy-3-methylbutyl]carbamoylamino]pentanedioic acid

There total 6 articles about (2S)-2-[[(1S)-1-carboxy-3-methylbutyl]carbamoylamino]pentanedioic 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: 100.0%

(S)-dibenzyl 2-(3-((S)-1-(benzyloxy)-4-methyl-1-oxopentan-2-yl)ureido)pentanedioate → ZJ-43 (723331-20-2)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In ethyl acetate; for 12h; under 1551.49 Torr;

DOI:10.1016/j.bmc.2018.11.022

Reference yield: 98.0%

C20H36N2O7 → ZJ-43 (723331-20-2)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 1.33333h;

DOI:10.1002/anie.201806966

Reference yield: 39.0%

(S)-di-tert-butyl 2-(3-((S)-1-(tert-butoxy)-4-methyl-1-oxopentan-2-yl)ureido)pentanedioate → ZJ-43 (723331-20-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 3h;

DOI:10.1016/j.bioorg.2020.104304

upstream raw materials:

L-glutamic acid di-tert-butyl ester hydrochloride

L-leucine hydrochloride

L-Leucine benzyl ester

dibenzyl L-glutamate