Gln

Glutamine

L-Glutamine
Names
IUPAC name Glutamine
Other names L-Glutamine (levo)glutamide 2-Amino-4-carbamoylbutanoic acid Endari
Identifiers
CAS Number	56-85-9 Y
3D model (JSmol)	Interactive image
Abbreviations	Gln, Q
ChEBI	CHEBI:28300 Y
ChEMBL	ChEMBL930 N
ChemSpider	718 Y
ECHA InfoCard	100.000.266
EC Number	200-292-1
IUPHAR/BPS	723
KEGG	C00303 Y
PubChem CID	738
UNII	0RH81L854J Y
InChI InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10) Y Key: ZDXPYRJPNDTMRX-UHFFFAOYSA-N Y InChI=1/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10) Key: ZDXPYRJPNDTMRX-UHFFFAOYAL
SMILES O=C(N)CCC(N)C(=O)O
Properties
Chemical formula	C5H10N2O3
Molar mass	146.15 g·mol−1
Melting point	decomposes around 185°C
Solubility in water	soluble
Acidity (pKa)	2.2 (carboxyl), 9.1 (amino)
Chiral rotation ([α]D)	+6.5º (H2O, c = 2)
Pharmacology
ATC code	A16AA03 (WHO)
Supplementary data page
Structure and properties	Refractive index (n), Dielectric constant (εr), etc.
Thermodynamic data	Phase behaviour solid–liquid–gas
Spectral data	UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Glutamine (symbol Gln or Q; encoded by the codons CAA and CAG) is an α-amino acid that is used in the biosynthesis of proteins. Its side chain is similar to that of glutamic acid, except the carboxylic acid group is replaced by an amide. It is classified as a charge-neutral, polar amino acid. It is non-essential and conditionally essential in humans, meaning the body can usually synthesize sufficient amounts of it, but in some instances of stress, the body's demand for glutamine increases, and glutamine must be obtained from the diet.

In human blood, glutamine is the most abundant free amino acid.

The dietary sources of glutamine includes especially the protein-rich foods like beef, chicken, fish, dairy products, eggs, vegetables like beans, beets, cabbage, spinach, carrots, parsley, vegetable juices and also in wheat, papaya, brussel sprouts, celery, kale and fermented foods like miso.

Glutamine plays a role in a variety of biochemical functions:

On the level of tissue, glutamine plays a role in maintaining the normal integrity of the intestinal mucosa., but randomised trials provide no evidence of any benefit of nutritional supplementation.

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 lungs and 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 many cancer cells.

Glutamine is the most abundant naturally occurring, nonessential amino acid in the human body, and one of the few amino acids that can directly cross the blood–brain barrier. Humans obtain glutamine through catabolism of proteins in foods they eat. In states where tissue is being built or repaired, like growth of babies, or healing from wounds or severe illness, glutamine becomes conditionally essential.