(2R)-5-amino-2-azaniumyl-5-oxopentanoate

Base Information

• Chemical Name: (2R)-5-amino-2-azaniumyl-5-oxopentanoate
• CAS No.: 5959-95-5
• Molecular Formula: C5H10N2O3
• Molecular Weight: 146.146
• Hs Code.: 29241900
• Mol file: 5959-95-5.mol

Synonyms:glutamide;D-glutamine zwitterion;CHEBI:58000;(2R)-5-amino-2-azaniumyl-5-oxopentanoate

Chemical Property of (2R)-5-amino-2-azaniumyl-5-oxopentanoate

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 184-185 °C
• Refractive Index: -33 ° (C=5, 5mol/L HCl)
• Boiling Point: 445.6 °C at 760 mmHg
• PKA: 2.27±0.10(Predicted)
• Flash Point: 223.3 °C
• PSA: 106.41000
• Density: 1.321 g/cm³
• LogP: 0.06440
• Storage Temp.: -15°C
• Solubility.: Water (Slightly, Sonicated)
• Water Solubility.: 42.53g/L(temperature not stated)
• XLogP3: -2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 146.06914219
• Heavy Atom Count: 10
• Complexity: 140

Purity/Quality:

99% ^*data from raw suppliers

D-Glutamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 36/37/39-26-27-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CC(=O)N)C(C(=O)[O-])[NH3+]
• Isomeric SMILES: C(CC(=O)N)[C@H](C(=O)[O-])[NH3+]
• Uses: D-Glutamine is an unnatural isomer of L-Glutamine (G597000) that is present in human plasma an is a source of liberated ammonia. D-Glutamine can be synthesized by enzymatic means or can be found in cheeses, wine and vinegars as well. It is often used to determine the activity of Glutamine synthetase, an enzyme that is commonly found in the mammalian liver and brain that controls the use of nitrogen in cells. D-Glutamine has been used to study its role in conferring protection against acetaldehyde-induced disruption of barrier function in Caco-2 cell monolayer.

Technology Process of (2R)-5-amino-2-azaniumyl-5-oxopentanoate

There total 28 articles about (2R)-5-amino-2-azaniumyl-5-oxopentanoate 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: 90.0%

2-phthalimidoglutaramic acid (7607-72-9,2110-19-2,174591-46-9) → GLUTAMINE (56-85-9,585-21-7,5959-95-5,6899-04-3,26700-71-0)

Guidance literature:

With hydrazine hydrate; In water; at 20 ℃; for 48h;

DOI:10.1016/j.molstruc.2020.128600

Reference yield:

→ GLUTAMINE (56-85-9,585-21-7,5959-95-5,6899-04-3,26700-71-0) + Glutamic acid (617-65-2,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6)

Guidance literature:

Reference yield:

N-phthalylglutamic acid (6349-98-0,2301-52-2) → GLUTAMINE (56-85-9,585-21-7,5959-95-5,6899-04-3,26700-71-0)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic anhydride / 0.25 h / Reflux

2: ammonia / 0.33 h / 20 °C

3: hydrazine hydrate / water / 48 h / 20 °C

With ammonia; acetic anhydride; hydrazine hydrate; In water;

DOI:10.1016/j.molstruc.2020.128600

upstream raw materials:

6-oxo-1,4,5,6-tetrahydropyridazine-3-carboxylic acid

L-glutamine

theanyl-L-alanine (H-Tea-L-Ala-OH)

ammonia

Downstream raw materials:

Nα-benzyloxycarbonyl-glutamine

nicotinamide

N-benzoylglutamine

4-Carbamoyl-2-(2,2,2-trifluoro-acetylamino)-butyric acid

Refernces

• 1、 Du, Qinglin,Zhang, Xiangyang,Pan, Xinru,Zhang, Hongjuan,Yang, Yu-Shun,Liu, Junzhong,Jiao, Qingcai. "A novel strategy for efficient chemoenzymatic synthesis of D-glutamine using recombinant Escherichia coli cells". . . Retrieved 2020/06/17.
• 2、 Wu, Peng,Wu, Yuping,Zhang, Junhui,Lu, Zhenyu,Zhang, Mei,Chen, Xuexian,Yuan, Liming. "Chromatographic Resolution of α-Amino Acids by (R)-(3,3'-Halogen Substituted-1,1'-binaphthyl)-20-crown-6 Stationary Phase in HPLC". supporting information. p. 1037 - 1042. Retrieved 2017/07/25.