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L-Glutamine

Names

[ CAS No. ]:
56-85-9

[ Name ]:
L-Glutamine

[Synonym ]:
UNII-U5JDO2770Z
EINECS 200-292-1
(2S)-2-((2S)-2-Aminopropanoylamino)-4-carbamoylbutanoic acid
ZY1&VMYVQ2VZ &&L-L Form
glutaminic acid
Gln
L-Ala-L-Gln
glutamine
L-Gln
Pentanoic acid, 2,5-diamino-5-oxo-, (S)-
L-Alanyl-L-glutamine
Levoglutamide
(S)-5-Amino-2-[(S)-2-aminopropanamido]-5-oxopentanoic acid
L-Glutamine,L-alanyl
2,5-Diamino-5-oxopentanoic acid, (S)-
(2S)-2-amino-4-carbamoylbutanoic acid
Alanyl-glutamine,Glutamine-S
MFCD00008044
Ala-Gln
L-(+)-Glutamine
2-Aminoglutaramic acid, L-
(S)-(+)-Glutamine
5-Hydroxy-5-imino-L-norvaline
N(2)-L-alanyl-L-glutamine
Glutamine-S
Alanyl-glutamine
L-Norvaline, 5-hydroxy-5-imino-
L-Glutamic Acid g-Amide
L-Glutamic acid γ-amide
N-L-alanyl-L-glutamine
L-Glutamine, N2-L-alanyl-
L-Glutamine
l-alanyl-l-glutamin
l-(+)-glutamic acid-5-amide
L-Glutamic acid 5-amide
H-Ala-Gln-OH
GLUTAMINE, L-
(2S)-5-Amino-2-{[(2S)-2-aminopropanoyl]amino}-5-oxopentanoic acid
L-Glutamine, L-alanyl-
S(+)-Glutamic acid 5-amide
H-Gln-OH

Biological Activity

[Description]:

L-Glutamine is a non-essential amino acid present abundantly throughout the body and is involved in gastrointestinal disorders.Target: mGluRGlutamine (abbreviated as Gln or Q) is one of the 20 amino acids encoded by the standard genetic code. It is not recognized as an essential amino acid, but may become conditionally essential in certain situations, including intensive athletic training or certain gastrointestinal disorders. Its side-chain is an amide formed by replacing the side-chain hydroxyl of glutamic acid with an amine functional group, making it the amide of glutamic acid. Its codons are CAA and CAG. In human blood, glutamine is the most abundant free amino acid, with a concentration of about 500-900 μmol/L. Glutamine is synthesized by the enzyme glutamine synthetase from glutamate and ammonia. The most relevant glutamine-producing tissue is the muscle mass, accounting for about 90% of all glutamine synthesized. Glutamine is also released, in small amounts, by the lung and the brain. Although the liver is capable of relevant glutamine synthesis, its role in glutamine metabolism is more regulatory than producing, since the liver takes up large amounts of glutamine derived from the gut. The most eager consumers of glutamine are the cells of intestines, the kidney cells for the acid-base balance, activated immune cells, and manycancer cells. In respect to the last point mentioned, different glutamine analogues, such as DON, Azaserine or Acivicin, are tested as anticancer drugs.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> mGluR
Research Areas >> Metabolic Disease
Natural Products >> Others

[Target]

Human Endogenous Metabolite


[References]

[1]. Brosnan JT. Interorgan amino acid transport and its regulation. J Nutr. 2003 Jun;133(6 Suppl 1):2068S-2072S.

[2]. Newsholme P, et al. Glutamine and glutamate as vital metabolites. Braz J Med Biol Res. 2003 Feb;36(2):153-63. Epub 2003 Jan 29.

[3]. Newsholme P. Why is L-glutamine metabolism important to cells of the immune system in health, postinjury, surgery or infection? J Nutr. 2001 Sep;131(9 Suppl):2515S-22S; discussion 2523S-4S.


[Related Small Molecules]

3-Methyladenine | Hydrocortisone | Acetylcysteine(N-acetylcysteine) | Retinoic acid | Melatonine | Dinoprostone | Nicotinamide | Adenosine triphosphate | 4-Acetamidophenol | Prostaglandin E1 | Dehydroepiandrosterone | Corticosterone | Progesterone | Docosahexaenoic Acid | NAD+

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
353.5±52.0 °C at 760 mmHg

[ Melting Point ]:
185ºC

[ Molecular Formula ]:
C5H10N2O3

[ Molecular Weight ]:
146.145

[ Flash Point ]:
167.6±30.7 °C

[ Exact Mass ]:
146.069138

[ PSA ]:
106.41000

[ LogP ]:
-1.28

[ Vapour Pressure ]:
0.0±1.8 mmHg at 25°C

[ Index of Refraction ]:
1.564

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
MA2275100
CHEMICAL NAME :
Glutamine, L-
CAS REGISTRY NUMBER :
56-85-9
BEILSTEIN REFERENCE NO. :
1723797
LAST UPDATED :
199706
DATA ITEMS CITED :
7
MOLECULAR FORMULA :
C5-H10-N2-O3
MOLECULAR WEIGHT :
146.17
WISWESSER LINE NOTATION :
ZV2YZVQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
27 mg/kg/1W-I
TOXIC EFFECTS :
Behavioral - euphoria
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
7500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
21700 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
260 mg/kg/30D-I
TOXIC EFFECTS :
Behavioral - food intake (animal) Blood - changes in spleen Related to Chronic Data - death

MUTATION DATA

TYPE OF TEST :
Sister chromatid exchange
TEST SYSTEM :
Human Lymphocyte
DOSE/DURATION :
10 mg/L
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 372,75,1996 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4814 No. of Facilities: 841 (estimated) No. of Industries: 4 No. of Occupations: 14 No. of Employees: 8491 (estimated) No. of Female Employees: 5700 (estimated)

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36

[ Safety Phrases ]:
S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
MA2275100

[ HS Code ]:
2932999099

Synthetic Route

Precursor & DownStream

Customs

[ HS Code ]: 2924199090

[ Summary ]:
2924199090. other acyclic amides (including acyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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