(2S)-2-amino-4-carbamoylbutanoic acid

• ChemBase ID: 16
• Molecular Formular: C5H10N2O3
• Molecular Mass: 146.1445
• Monoisotopic Mass: 146.06914219
• SMILES: OC(=O)[C@@H](N)CCC(=O)N
• Canonical SMILES: NC(=O)CC[C@@H](C(=O)O)N
• InChI: InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m0/s1
• InChIKey: ZDXPYRJPNDTMRX-VKHMYHEASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-carbamoylbutanoic acid
• IUPAC Traditional name: L-glutamine
• Brand Name: Glutamine Fuel Powder (Twinlab); Glutamine Fuel Mega (Twinlab); Glutamine Express (Genetic Evolutionary Nutrition); L-Glutamine Power (Champion Nutrition); Earthlink Science Glutamine Chews Chocolate (Amerifit); Cebrogen; Stimulina; Glavamin; Saforis
• Synonyms: Acustasin; Aesgen 14; Cebrogen; Glumin; L-2-Aminoglutaramidic Acid; L-Glutamic Acid γ-Αmide; NSC 27421; Saforis; γ-Glutamine; L-Glutamine solution; L-Glutamine; Glutamine; (S)-2,5-Diamino-5-oxopentanoic acid; L-Glutamic acid 5-amide; L-2-Aminoglutaramic acid; H-Gln-OH; Proteinogene aminos?uren und stereoisomer D-formen und ihre salze mit gegenionen der WGK 1; Stimulina; Levoglutamide; L-GLUTAMINE, USP GRADE; L-Glutamine Powder; L-Glutamine solution; L-Glutamine Solution 200 mM; 2-Aminoglutaramic acid; Glutamine; L-glutamine; AES-14; L-Glutamine; L-谷氨酰胺 溶液; (S)-2,5-二氨基-5-氧代戊酸; L-谷氨酸-5-酰胺; L-谷氨酰胺; L-谷氨酰胺 溶液; L-谷氨酰胺溶液 200mM

Database IDs

• CAS Number: 56-85-9
• EC Number: 200-292-1
• MDL Number: MFCD00008044
• Beilstein Number: 1723797
• Merck Index: 144471
• PubChem SID: 24872884; 24277983; 24895342; 160963479; 24895088; 24895310; 24895232; 46505866; 24895254
• PubChem CID: 5961
• FEMA ID: 3684
• Flavis Number: 17.007

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.1471426
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -4.001106
• LogD (pH = 7.4): -4.0058823
• Log P: -4.0011334
• Molar Refractivity: 33.1099 cm^3
• Polarizability: 13.317601 Å^3
• Polar Surface Area: 106.41 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -3.32
• LOG S: -0.17
• Solubility (Water): 9.78e+01 g/l

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 M at 20 °C, clear, colorless; H2O: soluble25 mg/mL; Slight (0.1-1%); Water
• Apperance: dry powder; powder; solution; White Solid
• Melting Point: 177-179°C; 185 °C (dec.)(lit.); 185°C; 185°C dec.
• Optical Rotation: [α]20/D +33.0±1°, c = 5% in 5 M HCl; [α]20/D +34±2°, c = 5% in 5 M HCl; [α]25/D +31°, c = 2 in 1 M HCl; +33 (c=5 in 5N HCl)
• Absorption Wavelength: λ: 260 nm Amax: 0.01; λ: 280 nm Amax: 0.01
• Hydrophobicity(logP): -4.1
• pH: 5.0-6.0 (25 °C, 0.1 M in H2O)

Safety Information

• Storage Condition: -20°C; Refrigerator; Room Temperature (15-30°C)
• RTECS: MA2275100
• German water hazard class: 1
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; room temp

Pharmacology Properties

• Gene Information: rat ... Ggt1(116568)

Product Information

• Purity: ≥99%; ≥99% (TLC); ≥99.0%; ≥99.0% (NT); ≥99.5% (NT); 97%; 98%; 98.5-101.5%; 99%; 99.0-101.0%; 99-100%
• Concentration: 200 mM
• Grade: certified reference material; Hybri-Max™; ReagentPlus®; SAJ special grade; TraceCERT®; USP
• Salt Data: Free Base
• Packaging: pkg of 1 g; vial of 0.292 g
• Suitability: cell culture tested; meets USP testing specifications; suitable for cell culture; suitable for hybridoma; suitable for manufacturing use
• Ignition Residue: ≤0.1% (as SO4)
• Description: for research or for further manufacturing use
• Impurities: ~0.5% Glutamic acid; ≤0.2% free ammonia.; ≤0.5% foreign amino acids; endotoxin, tested; insoluble matter, passes filter test
• Cation Traces: Al: ≤5 mg/kg; As: ≤0.1 mg/kg; Ba: ≤5 mg/kg; Bi: ≤5 mg/kg; Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Li: ≤5 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: ≤50 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Sr: ≤5 mg/kg; Zn: ≤5 mg/kg
• Antion Traces: chloride (Cl-): ≤50 mg/kg; sulfate (SO42-): ≤50 mg/kg
• Biological Source: from non-animal source
• Sterility: sterile-filtered; γ-irradiated
• Loss on Drying: ≤0.1% loss on drying, 110 °C
• Quality Level: GMP; GMP-COMPENDIA
• Shipped in: dry ice
• λ: 0.1 M in H2O
• Product Line: BioUltra
• Pharmacopeia Traceability: traceable to USP 1294808
• Linear Formula: H2NCOCH2CH2CH(NH2)CO2H

DETAILS

MP Biomedicals - 02101806

Crystalline
Purity: 99-100%
We believe this to be the best material available anywhere. Completely homogeneous by TLC showing one spot.

MP Biomedicals - 02194678

Cell Culture Reagent Crystalline Purity: 99-100%

MP Biomedicals - 02199608

White Crystalline Powder.
Assay: 98.5-101.5%
Specific rotation: +6.3 to +7.3
Loss on drying: <0.3%
Residue on ignition: <0.3%
Chloride: <0.5%
Sulfate: <0.03%
Iron: <0.003%
Heavy metals: <0.0015%
Organic volatile impurities: passes

DrugBank - DB00130

• Drug Groups: approved; nutraceutical; investigational
• Description: A non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from glutamic acid and ammonia. It is the principal carrier of nitrogen in the body and is an important energy source for many cells. [PubChem]
• Indication: Used for nutritional supplementation, also for treating dietary shortage or imbalance.
• Pharmacology: Like other amino acids, glutamine is biochemically important as a constituent of proteins. Glutamine is also crucial in nitrogen metabolism. Ammonia (formed by nitrogen fixation) is assimilated into organic compounds by converting glutamic acid to glutamine. The enzyme which accomplishes this is called glutamine synthetase. Glutamine can then be used as a nitrogen donor in the biosynthesis of many compounds, including other amino acids, purines, and pyrimidines.
• Toxicity: Doses of L-glutamine up to 21 grams daily appear to be well tolerated. Reported adverse reactions are mainly gastrointestinal and not common. They include constipation and bloating. There is one older report of two hypomanic patients whose manic symptoms were exacerbated following the use of 2 to 4 grams daily of L-glutamine. The symptoms resolved when the L-glutamine was stopped. These patients were not rechallenged, nor are there any other reports of this nature.
• Affected Organisms: Humans and other mammals
• Biotransformation: Enterocytes, Hepatic
• Absorption: Absorption is efficient and occurs by an active transport mechanism
• References: Boza JJ, Dangin M, Moennoz D, Montigon F, Vuichoud J, Jarret A, Pouteau E, Gremaud G, Oguey-Araymon S, Courtois D, Woupeyi A, Finot PA, Ballevre O: Free and protein-bound glutamine have identical splanchnic extraction in healthy human volunteers. Am J Physiol Gastrointest Liver Physiol. 2001 Jul;281(1):G267-74. [Pubmed] ; McAnena OJ, Moore FA, Moore EE, Jones TN, Parsons P: Selective uptake of glutamine in the gastrointestinal tract: confirmation in a human study. Br J Surg. 1991 Apr;78(4):480-2. [Pubmed] ; Morlion BJ, Stehle P, Wachtler P, Siedhoff HP, Koller M, Konig W, Furst P, Puchstein C: Total parenteral nutrition with glutamine dipeptide after major abdominal surgery: a randomized, double-blind, controlled study. Ann Surg. 1998 Feb;227(2):302-8. [Pubmed] ; Jian ZM, Cao JD, Zhu XG, Zhao WX, Yu JC, Ma EL, Wang XR, Zhu MW, Shu H, Liu YW: The impact of alanyl-glutamine on clinical safety, nitrogen balance, intestinal permeability, and clinical outcome in postoperative patients: a randomized, double-blind, controlled study of 120 patients. JPEN J Parenter Enteral Nutr. 1999 Sep-Oct;23(5 Suppl):S62-6. [Pubmed]
• External Links: Wikipedia; PDRhealth

Selleck Chemicals - S1749

Research Area: Metabolic Disease
Biological Activity:
L-Glutamine is one of the 20 amino acids encoded by the standard genetic code. Its codons are CAA and CAG. Glutamine is a substance naturally produced in the body to help regulate cell growth and function. There may also be man-made versions of these substances. Glutamine is used along with human growth hormone and a specialized diet to treat short bowel syndrome. 

Sigma Aldrich - 59202C

Biochem/physiol Actions
L-glutamine is an essential amino acid that is a crucial component of culture media that serves as a major energy source for cells in culture. L-glutamine is very stable as a dry powder and as a frozen solution. In liquid media or stock solutions, however, L-glutamine degrades relatively rapidly. Optimal cell performance usually requires supplementation of the media with L-glutamine prior to use.
Protocols & Applications
ECACC Handbook-Fundamental Techniques in Cell Culture

Sigma Aldrich - G6392

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
L-谷氨酰胺是一种基本氨基酸，是作为细胞培养主要能源的培养基所必不可少的组成部分。L-谷氨酰胺干粉和冷冻溶液十分稳定。但液体培养基或储存液中的 L-谷氨酰胺分解相对较快。使用前，通常需要补充含·L-谷氨酰胺的培养基，以获得最佳细胞性能。
L-glutamine is an essential amino acid that is a crucial component of culture media, and serves as a major energy source for cells in culture. Optimal cell performance usually requires supplementation of the medium with L-glutamine prior to use.
包装
50 mL amber serum vial with rubber stopper.
Reconstitution
Prepares a 200 mM solution when reconstituted to 10 mL with sterile water.
Suitability
Qualified for use in cell culture applications, especially serum-free cell culture.
Other Notes
The dipeptide L-Ala-LGln is frequently used in modern serum-free media formulations because it provides a more stable form of glutamine in vitro.

Sigma Aldrich - G3126

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
L-谷氨酰胺是一种基本氨基酸，是作为细胞培养主要能源的培养基所必不可少的组成部分。L-谷氨酰胺干粉和冷冻溶液十分稳定。但液体培养基或储存液中的 L-谷氨酰胺分解相对较快。使用前，通常需要补充含·L-谷氨酰胺的培养基，以获得最佳细胞性能。
包装
1 kg in poly bottle
100, 250, 500 g in poly bottle
法律信息
ReagentPlus 注册商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - G8540

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
L-谷氨酰胺是一种基本氨基酸，是作为细胞培养主要能源的培养基所必不可少的组成部分。L-谷氨酰胺干粉和冷冻溶液十分稳定。但液体培养基或储存液中的 L-谷氨酰胺分解相对较快。使用前，通常需要补充含·L-谷氨酰胺的培养基，以获得最佳细胞性能。
包装
10 mg in autosmp vl

Sigma Aldrich - 49419

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
L-Glutamine is an essential amino acid that is a crucial component of culture media that serves as a major energy source for cells in culture. L-Glutamine is very stable as a dry powder and as a frozen solution. In liquid media or stock solutions, however, L-glutamine degrades relatively rapidly. Optimal cell performance usually requires supplementation of the media with L-glutamine prior to use.
Other Notes
In culture medium for hypothalamic neurons1; Spacer in isotachophoresis of serum proteins2; Growth requirement of various microorganisms3.

Sigma Aldrich - G7513

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
L-谷氨酰胺是一种基本氨基酸，是作为细胞培养主要能源的培养基所必不可少的组成部分。L-谷氨酰胺干粉和冷冻溶液十分稳定。但液体培养基或储存液中的 L-谷氨酰胺分解相对较快。使用前，通常需要补充含 L-谷氨酰胺的培养基，以获得最佳细胞性能。
Preparation Note
用细胞培养级超纯水制备。
Application
L-glutamine is an essential amino acid that is a crucial component of culture media, which serves as a major energy source for cells in culture. Optimal cell performance usually requires supplementation of the medium with L-glutamine prior to use.

Sigma Aldrich - G2150

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
L-谷氨酰胺是一种基本氨基酸，是作为细胞培养主要能源的培养基所必不可少的组成部分。L-谷氨酰胺干粉和冷冻溶液十分稳定。但液体培养基或储存液中的 L-谷氨酰胺分解相对较快。使用前，通常需要补充含 L-谷氨酰胺的培养基，以获得最佳细胞性能。
Preparation Note
Prepared in cell culture grade water.
法律信息
Hybri-Max 商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - G5792

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
L-Glutamine is an essential amino acid that is a crucial component of culture media that serves as a major energy source for cells in culture. L-Glutamine is very stable as a dry powder and as a frozen solution. In liquid media or stock solutions, however, L-glutamine degrades relatively rapidly. Optimal cell performance usually requires supplementation of the media with L-glutamine prior to use.
Packaging
Manufactured and packaged under cGMP

Sigma Aldrich - 90114C

Biochem/physiol Actions
L-Glutamine is an essential amino acid that is a crucial component of culture media that serves as a major energy source for cells in culture. L-Glutamine is very stable as a dry powder and as a frozen solution. In liquid media or stock solutions, however, L-glutamine degrades relatively rapidly. Optimal cell performance usually requires supplementation of the media with L-glutamine prior to use.

Sigma Aldrich - W368401

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
L-Glutamine is an essential amino acid that is a crucial component of culture media that serves as a major energy source for cells in culture. L-Glutamine is very stable as a dry powder and as a frozen solution. In liquid media or stock solutions, however, L-glutamine degrades relatively rapidly. Optimal cell performance usually requires supplementation of the media with L-glutamine prior to use.
Packaging
1 kg in poly bottle

Sigma Aldrich - G3202

Biochem/physiol Actions
L-Glutamine is an essential amino acid that is a crucial component of culture media that serves as a major energy source for cells in culture. L-Glutamine is very stable as a dry powder and as a frozen solution. In liquid media or stock solutions, however, L-glutamine degrades relatively rapidly. Optimal cell performance usually requires supplementation of the media with L-glutamine prior to use.
Packaging
2.5 g in glass bottle

Sigma Aldrich - 12-0950

Biochem/physiol Actions
L-Glutamine is an essential amino acid that is a crucial component of culture media that serves as a major energy source for cells in culture. L-Glutamine is very stable as a dry powder and as a frozen solution. In liquid media or stock solutions, however, L-glutamine degrades relatively rapidly. Optimal cell performance usually requires supplementation of the media with L-glutamine prior to use.

Sigma Aldrich - 76523

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Analysis Note
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34. This CRM is traceable to NIST SRM.
Biochem/physiol Actions
L-Glutamine is an essential amino acid that is a crucial component of culture media that serves as a major energy source for cells in culture. L-Glutamine is very stable as a dry powder and as a frozen solution. In liquid media or stock solutions, however, L-glutamine degrades relatively rapidly. Optimal cell performance usually requires supplementation of the media with L-glutamine prior to use.
General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 49420

Biochem/physiol Actions
L-Glutamine is an essential amino acid that is a crucial component of culture media that serves as a major energy source for cells in culture. L-Glutamine is very stable as a dry powder and as a frozen solution. In liquid media or stock solutions, however, L-glutamine degrades relatively rapidly. Optimal cell performance usually requires supplementation of the media with L-glutamine prior to use.

Sigma Aldrich - PHR1125

Biochem/physiol Actions
L-Glutamine is an essential amino acid that is a crucial component of culture media that serves as a major energy source for cells in culture. L-Glutamine is very stable as a dry powder and as a frozen solution. In liquid media or stock solutions, however, L-glutamine degrades relatively rapidly. Optimal cell performance usually requires supplementation of the media with L-glutamine prior to use.
General description
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34.
Other Notes
Values of analytes vary lot to lot.

Toronto Research Chemicals - G597000

L-Glutamine is an essential amino acid that is a crucial component of culture media that serves as a major energy source for cells in culture. L-Glutamine is very stable as a dry powder and as a frozen solution. In liquid media or stock solutions, however

REFERENCES

• Boza JJ, Dangin M, Moennoz D, Montigon F, Vuichoud J, Jarret A, Pouteau E, Gremaud G, Oguey-Araymon S, Courtois D, Woupeyi A, Finot PA, Ballevre O: Free and protein-bound glutamine have identical splanchnic extraction in healthy human volunteers. Am J Physiol Gastrointest Liver Physiol. 2001 Jul;281(1):G267-74. Pubmed
• McAnena OJ, Moore FA, Moore EE, Jones TN, Parsons P: Selective uptake of glutamine in the gastrointestinal tract: confirmation in a human study. Br J Surg. 1991 Apr;78(4):480-2. Pubmed
• Morlion BJ, Stehle P, Wachtler P, Siedhoff HP, Koller M, Konig W, Furst P, Puchstein C: Total parenteral nutrition with glutamine dipeptide after major abdominal surgery: a randomized, double-blind, controlled study. Ann Surg. 1998 Feb;227(2):302-8. Pubmed
• Jian ZM, Cao JD, Zhu XG, Zhao WX, Yu JC, Ma EL, Wang XR, Zhu MW, Shu H, Liu YW: The impact of alanyl-glutamine on clinical safety, nitrogen balance, intestinal permeability, and clinical outcome in postoperative patients: a randomized, double-blind, controlled study of 120 patients. JPEN J Parenter Enteral Nutr. 1999 Sep-Oct;23(5 Suppl):S62-6. Pubmed
• Rivett, A., et al.: J. Biol. Chem., 260, 300 (1985)
• Watford, M., et al.: Metabolism, 49, 141 (1985)
• Wilmore, D., et al.: J. Nutr., 131, 2543S (1985)