gamma-Carboxyglutamate

Base Information

• Chemical Name: gamma-Carboxyglutamate
• CAS No.: 56271-99-9
• Molecular Formula: C6H9NO6
• Molecular Weight: 191.141
• Hs Code.: 2922499990
• European Community (EC) Number: 260-087-8
• UNII: 1K3CGY068S
• DSSTox Substance ID: DTXSID50872037
• Nikkaji Number: J2.206.709E
• Wikipedia: Carboxyglutamic_acid
• Wikidata: Q2823245
• Mol file: 56271-99-9.mol

Synonyms:1 Carboxyglutamic Acid;1-Carboxyglutamic Acid;3-Amino-1,1,3-propanetricarboxylic Acid;gamma Carboxyglutamate;gamma Carboxyglutamic Acid;gamma-Carboxyglutamate;gamma-Carboxyglutamic Acid

Chemical Property of gamma-Carboxyglutamate

Chemical Property:

• Appearance/Colour: Crystalline
• Vapor Pressure: 3.71E-08mmHg at 25°C
• Melting Point: 167 °C
• Refractive Index: 1.569
• Boiling Point: 418 °C at 760 mmHg
• PKA: 2.13±0.10(Predicted)
• Flash Point: 206.6 °C
• PSA: 137.92000
• Density: 1.649 g/cm³
• LogP: -0.72590
• Storage Temp.: 2-8°C
• XLogP3: -3.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 191.04298701
• Heavy Atom Count: 13
• Complexity: 223

Purity/Quality:

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

GLA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(C(C(=O)O)C(=O)O)C(C(=O)O)N

Technology Process of gamma-Carboxyglutamate

There total 8 articles about gamma-Carboxyglutamate 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: 73.0%

N-benzyloxycarbonyl-γ-carboxy-DL-glutamic acid (97458-26-9) → 2-amino-4-carboxypentanedioic acid (56271-99-9,53445-96-8)

Guidance literature:

With hydrogen; palladium; In methanol; water;

Reference yield: 5.0%

ethyl (+/-)-2,2-dimethyl-α-nitro-4,6-dioxo-1,3-dioxane-5-propanoate (176237-26-6) → 2-amino-4-carboxypentanedioic acid (56271-99-9,53445-96-8) + 5-Oxo-pyrrolidine-2,4-dicarboxylic acid 2-ethyl ester

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1055/s-1996-4201

Reference yield:

Z-γ,γ,-di-tert-butyl-D,L-carboxyglutamic acid methyl ester (56877-40-8) → 2-amino-4-carboxypentanedioic acid (56271-99-9,53445-96-8)

Guidance literature:

Multi-step reaction with 3 steps

1: KOH / ethanol

2: H₂ / Pd-C / methanol; ethyl acetate

3: aq. CF₃CO₂H

With potassium hydroxide; hydrogen; trifluoroacetic acid; palladium on activated charcoal; In methanol; ethanol; ethyl acetate;

DOI:10.1002/hlca.19750580525

upstream raw materials:

2-Benzyloxycarbonyl-4-benzyloxycarbonylamino-pentanedioic acid dibenzyl ester

γ,γ'-Di-tert-butyl-DL-γ-carboxyglutamic acid

N-benzyloxycarbonyl-γ-carboxy-DL-glutamic acid

ethyl (+/-)-2,2-dimethyl-α-nitro-4,6-dioxo-1,3-dioxane-5-propanoate

Downstream raw materials:

4-carboxy-4-D-5-phenylproline

4,4-dicarboxy-5-(p-methoxyphenyl)proline

4,4-dicarboxy-5-phenylproline

4,4-dicarboxy-5-(p-nitrophenyl)proline

Refernces

• 1、 Cerovsky, Vaclav,Jost, Karel. "ENZYMATIC RESOLUTION OF γ-CARBOXY-DL-GLUTAMIC ACID". . p. 2562 - 2565. Retrieved 2007/10/02.
• 2、 Maerki,Schwyzer. "Preparation of DL-N-benzyloxycarbonyl-gamma-carboxy-glutamic acid-gamma, gamma'-di-t-butyl-alpha-methyl ester, a suitable derivative for peptide synthesis with the new aminotricarboxylic acid from prothrombin". . p. 1471 - 1477. Retrieved 2007/10/07.