L-Glutamine

Modify Date: 2024-01-02 17:38:57

L-Glutamine Structure
L-Glutamine structure
 Common Name L-Glutamine
CAS Number 56-85-9 Molecular Weight 146.145
Density 1.5±0.1 g/cm3 Boiling Point 353.5±52.0 °C at 760 mmHg
Molecular Formula C5H10N2O3 Melting Point 185ºC
MSDS Chinese USA Flash Point 167.6±30.7 °C

 Use of L-Glutamine


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.

 Names

Name L-glutamine
Synonym More Synonyms

 L-Glutamine 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
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.

 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

 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

 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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 Synonyms

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
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