Glutamine

From Infogalactic: the planetary knowledge core
Jump to: navigation, search

<templatestyles src="Module:Hatnote/styles.css"></templatestyles>

"Gln" redirects here. For other uses, see GLN (disambiguation).
L-Glutamine
Glutamine physiological pH.svg
Skeletal formula of the L-isomer
Sample of L-Glutamine.jpg
Names
IUPAC name
Glutamine
Other names
L-Glutamine
(levo)glutamide
2-Amino-4-carbamoylbutanoic acid
Identifiers
56-85-9 YesY
Abbreviations Gln, Q
ChEBI CHEBI:28300 YesY
ChEMBL ChEMBL930 N
ChemSpider 718 YesY
EC Number 200-292-1
723
Jmol 3D model Interactive image
KEGG C00303 YesY
PubChem 738
UNII 0RH81L854J YesY
  • InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10) YesY
    Key: ZDXPYRJPNDTMRX-UHFFFAOYSA-N YesY
  • 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
  • O=C(N)CCC(N)C(=O)O
Properties[1]
C5H10N2O3
Molar mass 146.15 g·mol−1
Melting point decomposes around 185°C
soluble
Acidity (pKa) 2.2 (carboxyl), 9.1 (amino)
+6.5º (H2O, c = 2)
Pharmacology
ATC code A16AA03
Vapor pressure {{{value}}}
Supplementary data page
Refractive index (n),
Dielectric constant (εr), etc.
Thermodynamic
data
 Phase behaviour
solid–liquid–gas
UV, IR, NMR, MS
N verify (what is YesYN ?)
Infobox references

Glutamine (abbreviated as Gln or Q; encoded by the codons CAA and CAG) is an ɑ-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated -+NH3 form under biological conditions), an α-carboxylic acid group (which is in the deprotonated –COO- form under biological conditions), and a side chain amide which replaces the side chain hydroxyl of glutamic acid with an amine functional group, classifying it as a charge neutral, polar (at physiological pH) 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.[2][3]

In human blood, glutamine is the most abundant free amino acid, with a concentration of about 500–900 µmol/l.[4]

Functions

Glutamine plays a role in a variety of biochemical functions:

Producing and consuming organs

Producers

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.[8] 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.[4]

Consumers

The most eager consumers of glutamine are the cells of intestines,[4] the kidney cells for the acid-base balance, activated immune cells,[9] and many cancer cells.[7]

Medical uses

In catabolic states of injury and illness, glutamine becomes conditionally essential requiring intake from food or supplements.[10]

Glutamine has been used as a component of oral supplementation to reverse cachexia (muscle wasting) in patients with advanced cancer[11] or HIV/AIDS.[12]

Glutamine oral supplementation significantly reduces the risk of systemic infections originating from the gut such as in critically ill individuals and in individuals who have had abdominal surgery. The reduction in rates of infections in these groups of people are due to glutamine improving intestinal barrier function including reducing increased intestinal permeability. Intravenous administration does not appear to produce these benefits, however.[13]

Supplementation does not appear to have an effect in infants with significant problems of the stomach or intestines.[14]

Research

In biological research, L-glutamine is commonly added to the media in cell culture.[15][16] However, the high level of glutamine in the culture media may inhibit other amino acid transport activities.[17]

Structure

Glutamine zwitterionic forms at neutral pH: L-glutamine (left) and D-glutamine

Nutrition

Occurrences in nature

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.[18] In the body, it is found circulating in the blood, as well as stored in the skeletal muscles. It becomes conditionally essential (requiring intake from food or supplements) in states of illness or injury.[10]

Dietary sources

Dietary sources of L-glutamine include beef, chicken, fish, eggs, milk, dairy products, wheat, cabbage, beets, beans, spinach, and parsley. Small amounts of free L-glutamine are also found in vegetable juices.[10]

See also

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found..
  2. ↑ Dietary Reference Intakes: The Essential Guide to Nutrient Requirements, published by the Institute of Medicine's Food and Nutrition Board, currently available online at http://fnic.nal.usda.gov/dietary-guidance/dietary-reference-intakes/dri-reports
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ 4.0 4.1 4.2 4.3 Lua error in package.lua at line 80: module 'strict' not found.open access publication - free to read
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ 7.0 7.1 Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ 10.0 10.1 10.2 Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  15. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  16. ↑ Yang H, Roth CM, Ierapetritou MG. (2011) Analysis of amino acid supplementation effects on hepatocyte cultures using flux balance analysis, OMICS, A Journal of Integrative Biology, 15(7-8): 449–460.
  17. ↑ Yang H, Ierapetritou MG, Roth CM. (2010) Effects of amino acid transport limitations on cultured hepatocytes, Biophysical Chemistry, 152(1-3):89-98.
  18. ↑ Lua error in package.lua at line 80: module 'strict' not found.

External links

Retrieved from "https://infogalactic.com/w/index.php?title=Glutamine&oldid=42892"