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56-85-9 molecular structure
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(2S)-2-amino-4-carbamoylbutanoic acid

ChemBase ID: 16
Molecular Formular: C5H10N2O3
Molecular Mass: 146.1445
Monoisotopic Mass: 146.06914219
SMILES and InChIs

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

Cite this record

CBID:16 http://www.chembase.cn/molecule-16.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
2-Aminoglutaramic acid
Glutamine
L-glutamine
AES-14
L-Glutamine
(S)-2,5-Diamino-5-oxopentanoic acid
L-Glutamic acid 5-amide
Proteinogene aminos?uren und stereoisomer D-formen und ihre salze mit gegenionen der WGK 1
Stimulina
Levoglutamide
L-GLUTAMINE, USP GRADE
L-2-Aminoglutaramic acid
L-Glutamine
L-Glutamine solution
L-Glutamine Solution 200 mM
Glutamine
Acustasin
Aesgen 14
Cebrogen
Glumin
L-2-Aminoglutaramidic Acid
L-Glutamic Acid γ-Αmide
NSC 27421
Saforis
L-Glutamine Powder
H-Gln-OH
γ-Glutamine
L-Glutamine solution
(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
L-谷氨酰胺 溶液
CAS Number
56-85-9
EC Number
200-292-1
MDL Number
MFCD00008044
Beilstein Number
1723797
Merck Index
144471
PubChem SID
46505866
160963479
24895088
24895342
24277983
24895310
24895232
24895254
24872884
PubChem CID
5961
FEMA ID
3684
Flavis Number
17.007

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 2.1471426  H Acceptors
H Donor LogD (pH = 5.5) -4.001106 
LogD (pH = 7.4) -4.0058823  Log P -4.0011334 
Molar Refractivity 33.1099 cm3 Polarizability 13.317601 Å3
Polar Surface Area 106.41 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -3.32  LOG S -0.17 
Solubility (Water) 9.78e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
H2O: soluble0.1 M at 20 °C, clear, colorless expand Show data source
H2O: soluble25 mg/mL expand Show data source
Slight (0.1-1%) expand Show data source
Water expand Show data source
Apperance
dry powder expand Show data source
powder expand Show data source
solution expand Show data source
White Solid expand Show data source
Melting Point
177-179°C expand Show data source
185 °C (dec.)(lit.) expand Show data source
185°C expand Show data source
185°C dec. expand Show data source
Optical Rotation
[α]20/D +33.0±1°, c = 5% in 5 M HCl expand Show data source
[α]20/D +34±2°, c = 5% in 5 M HCl expand Show data source
[α]25/D +31°, c = 2 in 1 M HCl expand Show data source
+33 (c=5 in 5N HCl) expand Show data source
Absorption Wavelength
λ: 260 nm Amax: 0.01 expand Show data source
λ: 280 nm Amax: 0.01 expand Show data source
Hydrophobicity(logP)
-4.1 expand Show data source
pH
5.0-6.0 (25 °C, 0.1 M in H2O) expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
Room Temperature (15-30°C) expand Show data source
RTECS
MA2275100 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
TSCA Listed
expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
room temp expand Show data source
Gene Information
rat ... Ggt1(116568) expand Show data source
Purity
≥99% expand Show data source
≥99% (TLC) expand Show data source
≥99.0% expand Show data source
≥99.0% (NT) expand Show data source
≥99.5% (NT) expand Show data source
97% expand Show data source
98% expand Show data source
98.5-101.5% expand Show data source
99% expand Show data source
99.0-101.0% expand Show data source
99-100% expand Show data source
Concentration
200 mM expand Show data source
Grade
certified reference material expand Show data source
Hybri-Max™ expand Show data source
ReagentPlus® expand Show data source
SAJ special grade expand Show data source
TraceCERT® expand Show data source
USP expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Packaging
pkg of 1 g expand Show data source
vial of 0.292 g expand Show data source
Suitability
cell culture tested expand Show data source
meets USP testing specifications expand Show data source
suitable for cell culture expand Show data source
suitable for hybridoma expand Show data source
suitable for manufacturing use expand Show data source
Ignition Residue
≤0.1% (as SO4) expand Show data source
Description
for research or for further manufacturing use expand Show data source
Impurities
~0.5% Glutamic acid expand Show data source
≤0.2% free ammonia. expand Show data source
≤0.5% foreign amino acids expand Show data source
endotoxin, tested expand Show data source
insoluble matter, passes filter test expand Show data source
Cation Traces
Al: ≤5 mg/kg expand Show data source
As: ≤0.1 mg/kg expand Show data source
Ba: ≤5 mg/kg expand Show data source
Bi: ≤5 mg/kg expand Show data source
Ca: ≤10 mg/kg expand Show data source
Cd: ≤5 mg/kg expand Show data source
Co: ≤5 mg/kg expand Show data source
Cr: ≤5 mg/kg expand Show data source
Cu: ≤5 mg/kg expand Show data source
Fe: ≤5 mg/kg expand Show data source
K: ≤50 mg/kg expand Show data source
Li: ≤5 mg/kg expand Show data source
Mg: ≤5 mg/kg expand Show data source
Mn: ≤5 mg/kg expand Show data source
Mo: ≤5 mg/kg expand Show data source
Na: ≤50 mg/kg expand Show data source
Ni: ≤5 mg/kg expand Show data source
Pb: ≤5 mg/kg expand Show data source
Sr: ≤5 mg/kg expand Show data source
Zn: ≤5 mg/kg expand Show data source
Antion Traces
chloride (Cl-): ≤50 mg/kg expand Show data source
sulfate (SO42-): ≤50 mg/kg expand Show data source
Biological Source
from non-animal source expand Show data source
Sterility
sterile-filtered expand Show data source
γ-irradiated expand Show data source
Loss on Drying
≤0.1% loss on drying, 110 °C expand Show data source
Quality Level
GMP expand Show data source
GMP-COMPENDIA expand Show data source
Shipped in
dry ice expand Show data source
λ
0.1 M in H2O expand Show data source
Product Line
BioUltra expand Show data source
Pharmacopeia Traceability
traceable to USP 1294808 expand Show data source
Linear Formula
H2NCOCH2CH2CH(NH2)CO2H expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich DrugBank DrugBank TRC TRC
Selleck Chemicals - S1749 external link
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. 
MP Biomedicals - 02101806 external link
Crystalline
Purity: 99-100%
We believe this to be the best material available anywhere. Completely homogeneous by TLC showing one spot.
MP Biomedicals - 02194678 external link
Cell Culture Reagent Crystalline Purity: 99-100%
MP Biomedicals - 02199608 external link
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
Sigma Aldrich - G6392 external link
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 external link
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 - 90114C external link
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 - 59202C external link
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 - 49420 external link
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 external link
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 - G5792 external link
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 - PHR1125 external link
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.
Sigma Aldrich - G8540 external link
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 - G7513 external link
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 - 49419 external link
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 - 76523 external link
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 - G2150 external link
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 - G3202 external link
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 external link
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.
DrugBank - DB00130 external link
Item Information
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
Toronto Research Chemicals - G597000 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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