N-Oxalylglycine

Base Information

• Chemical Name: N-Oxalylglycine
• CAS No.: 5262-39-5
• Molecular Formula: C4H5NO5
• Molecular Weight: 147.087
• Hs Code.: 2918300090
• European Community (EC) Number: 687-281-9
• UNII: VVW38EB8YS
• DSSTox Substance ID: DTXSID20200601
• Nikkaji Number: J499.245H
• Wikipedia: N-Oxalylglycine
• Pharos Ligand ID: QLM2JCMLHYJD
• ChEMBL ID: CHEMBL90852
• Mol file: 5262-39-5.mol

Synonyms:dimethyloxalylglycine;DMOG cpd;glycine, N-(carboxycarbonyl)-;N-(carboxycarbonyl)glycine;N-oxalylglycine;oxaloglycine;oxalylglycine;oxamic acid, (carboxymethyl)-

Chemical Property of N-Oxalylglycine

Chemical Property:

• Appearance/Colour: colourless solid
• Refractive Index: 1.521
• PKA: 2.83±0.20(Predicted)
• PSA: 103.70000
• Density: 1.638 g/cm³
• LogP: -1.33730
• Storage Temp.: 2-8°C
• Solubility.: deionized water: >10mg/mL
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 147.01677226
• Heavy Atom Count: 10
• Complexity: 175

Purity/Quality:

98%,99%, ^*data from raw suppliers

NOG ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(C(=O)O)NC(=O)C(=O)O
• Uses: The jumonji domain-containing protein 2 (JMJD2) subfamily of histone demethylases have been shown to catalyze demethylation of the methylated forms of histone 3 lysine 9 (H3K9) and H3K36 in vitro and in cells. Because histone demethylases are implicated in certain diseases, including cancer, selective inhibitors are candidate anticancer agents as well as potential tools for elucidating the biological functions of JMJDs. N-Oxalylglycine, the amide analog of α-ketoglutarate, is a cell permeable inhibitor of α-ketoglutarate-dependent enzymes, including JMJD2A, JMJD2C, and JMJD2E (IC50s = 250, 500, and 24 μM, respectively). It can also inhibit the prolyl hydroxylase domain-containing proteins PHD1 and PHD2 with IC50 values of 2.1 and 5.6 μM, respectively.[Cayman Chemical] Oxalylglycine is a broad-spectrum 2OG oxygenase inhibitor that is used in studies of the hypoxic response and chromatin modifications in animals. Oxalylglycine is present as a natural product in rhubarb and spinach leaves. It is also used as a reagent in the synthesis of bipyridinedicarboxylates which are inhibitors of CP4H and therefore may be used in the treatment of fibrotic diseases and metastatic breast cancer.

Technology Process of N-Oxalylglycine

There total 1 articles about N-Oxalylglycine 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:

2-(2,3-dioxo-3-phenylpropanamido)acetic acid (1159923-08-6) → N-oxalylglycine (5262-39-5) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With iron(III) sulfate; water; at 25 ℃; pH=4;

DOI:10.1002/anie.200806296

Reference yield: 77.0%

N-oxalylglycine (5262-39-5) + [κ3-N,N,O-bis(3,5-dimethyl-4-vinylpyrazol-1-yl)acetato](triphenylphosphine)chlororuthenium(I) → (κ3-N,N,O-bis(3,5-dimethyl-4-vinylpyrazol-1-yl)acetato)(κ2-N-oxalylglycinato)(triphenylphosphine)ruthenium(II)

Guidance literature:

With CH₃COOTl; In dichloromethane; (inert atm.), soln. of Ru complex in CH2Cl2 treated with TlOAc and N-oxalylglycinate (Ru:Tl:L=1:1.2:1.25), stirred at room temp. for 24 h; evapd.(vac.), washed (H2O, Et2O), crystd.(DMF/Et2O), elem. anal.;

DOI:10.1002/ejic.201000115

Reference yield: 75.0%

N-oxalylglycine (5262-39-5) + (κ3-N,N,O-bis(3,5-dimethyl-1-yl)acetato)(κ2-acetato)(triphenylphosphine)ruthenium(II) → (κ3-N,N,O-bis(3,5-dimethyl-4-vinylpyrazol-1-yl)acetato)(κ2-N-oxalylglycinato)(triphenylphosphine)ruthenium(II)

Guidance literature:

In dichloromethane; (inert atm.), soln. of Ru complex in CH2Cl2 treated with N-oxalylglycine, stirred at room temp. for 5 h; filtered, washed (CH2Cl2), dried (vac.), crystd.(CH3OH), elem. anal.;

DOI:10.1002/ejic.201000115

upstream raw materials:

2-(2,3-dioxo-3-phenylpropanamido)acetic acid

Refernces