Glutamine

Base Information

• Chemical Name: Glutamine
• CAS No.: 56-85-9
• Deprecated CAS: 32640-56-5,2087491-51-6
• Molecular Formula: C5H10N2O3
• Molecular Weight: 146.146
• Hs Code.: 2932999099
• European Community (EC) Number: 200-292-1
• NSC Number: 760081,759628
• UNII: 0RH81L854J
• DSSTox Substance ID: DTXSID1023100
• Nikkaji Number: J9.170G
• Wikipedia: Glutamine
• Wikidata: Q181619
• NCI Thesaurus Code: C522
• RXCUI: 4885
• Pharos Ligand ID: QB951RW7GUA9
• Metabolomics Workbench ID: 37346
• ChEMBL ID: CHEMBL930
• Mol file: 56-85-9.mol

Synonyms:D Glutamine;D-Glutamine;Glutamine;L Glutamine;L-Glutamine

Chemical Property of Glutamine

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 3.3E-24mmHg at 25°C
• Melting Point: 185 °C (dec.)(lit.)
• Refractive Index: 6.8 ° (C=4, H2O)
• Boiling Point: 445.6 °C at 760 mmHg
• Flash Point: 223.3 °C
• PSA: 106.41000
• Density: 1.321 g/cm³
• LogP: 0.06440
• Water Solubility.: H2O: 25 mg/mL
• XLogP3: -3.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 146.06914219
• Heavy Atom Count: 10
• Complexity: 146

Purity/Quality:

99% min ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi:刺激性物质
• Statements: R36:刺激眼睛
• Safety Statements: S24/25:

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Drug Classes: Sickle Cell Disease Agents
• Canonical SMILES: C(CC(=O)N)C(C(=O)O)N
• Isomeric SMILES: C(CC(=O)N)[C@@H](C(=O)O)N
• Recent ClinicalTrials: Efficacy of Glutamine in Management of Radiation Mucositis
• Recent EU Clinical Trials: ENSAYO CLíNICO ALEATORIZADO, DOBLE CIEGO Y CONTROLADO CON PLACEBO PARA EVALUAR EL USO DE LA GLUTAMINA COMO AGENTE PROTECTOR EN LA MUCOSITIS ORAL Y LA RADIODERMITIS INDUCIDA POR LA RADIOTERAPIA Y/O QUIMIOTERAPIA EN EL TRATAMIENTO DEL CáNCER DE CABEZA Y CUELLO
• Recent NIPH Clinical Trials: HMB study
• Abundance: Glutamine is the most abundant amino acid in the body, comprising 60% of the total pool of free amino acids.
• Synthesis Sources: The main synthesis sources of glutamine circulating in plasma are skeletal muscle, adipose tissue, and lungs.
• Nitrogen Transport: Glutamine performs most of the transport of nitrogen from skeletal muscle to visceral tissues.
• Primary Fuel: Glutamine is used as a glucose-efficient primary fuel for rapidly dividing cells, including enterocytes, colonocytes, lymphocytes, and fibroblasts.
• Acid-Base Balance: Glutamine plays a role in acid-base balance through ammonia production in the kidney.
• Biosynthesis Substrate: Its oxidized form provides the substrate for the synthesis of purines and pyrimidines necessary for DNA, RNA, and messenger RNA.
• Precursor to Glutathione: Glutamine is a precursor to glutathione, a powerful endogenously produced antioxidant.
• Research Importance: Glutamine is one of the most researched amino acids in medical nutritional care, including conditions such as gastrointestinal diseases, oncology, burn injury, HIV/AIDS, and chronic wound management.
• Role in Cell Metabolism: Glutamine supplies carbon and nitrogen to fuel biosynthesis, participating in tricarboxylic acid (TCA) cycle supplementation and the biosynthesis of nucleotides, glutathione (GSH), and other nonessential amino acids.
• Glutamine Deprivation: Glutamine deprivation suppresses cancer growth and induces cell death in several cancers due to its metabolic dependency, termed glutamine addiction.
• Glutaminase Inhibition: Specific genetic interference with glutaminase inhibits tumor cell growth, and CB-839, the first glutaminase inhibitor, has entered several clinical trials.
• Mitochondrial Glutamine Transporter: The mitochondrial glutamine transporter, encoded by a transcript variant of the SLC1A5 gene, was only recently discovered.
• Plasma Membrane Glutamine Transporters: Glutamine is transported into cells through plasma membrane glutamine transporters such as SLC1A5, SLC38A1, and SLC38A217, contributing to biosynthesis in the cytoplasm.

Technology Process of Glutamine

There total 67 articles about Glutamine 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:

(S)-4-Carbamoyl-2-[2-(4-methoxy-phenyl)-2-oxo-ethoxycarbonylamino]-butyric acid (125219-08-1) → L-glutamine (56-85-9,26700-71-0) + 1-(4-methoxyphenyl)ethanone (100-06-1)

Guidance literature:

Irradiation; mild conditions;

DOI:10.1016/S0040-4039(00)99608-4

Reference yield:

C48H63N9O13 → L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) + L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + L-glutamine (56-85-9,26700-71-0) + L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + N-methyl-L-tyrosine (537-49-5) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7)

Guidance literature:

With hydrogenchloride; In water; at 110 ℃; for 16h;

DOI:10.1021/np300150h

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

glycine

Refernces

S-2-Amino-4-cyanobutanoic acid (β-cyanomethyl-l-Ala) as an atom-efficient solubilising synthon for l-glutamine

10.1016/j.tetlet.2011.08.017

The study focuses on the development of an atom-efficient synthetic strategy for incorporating L-glutamine (L-Gln) into peptides during solution-phase synthesis. L-Gln is challenging to incorporate due to poor solubility and side reactions such as dehydration. The researchers propose using Na-Cbz-β-cyanomethyl-L-Ala (β-cyanomethyl-L-Ala) as a soluble and atom-efficient synthon for L-Gln. This synthon is stable under various conditions used in peptide synthesis and can be quantitatively hydrated to regenerate L-Gln within a peptide sequence. Key chemicals used include Cbz-L-Gln, dicyclohexylcarbodiimide (DCC), pyridine, hydrogen peroxide, and various protecting groups like Boc and OBut. These chemicals serve to dehydrate L-Gln to form the nitrile, protect and deprotect functional groups during synthesis, and facilitate peptide coupling reactions. The study demonstrates the utility of β-cyanomethyl-L-Ala in several peptide synthesis examples, showing its potential as a useful and efficient alternative for L-Gln incorporation in peptides.

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