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Glutamine

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Abbreviations
  
Gln, Q

Molar mass
  
146.14 g/mol

IUPAC ID
  
Glutamine

Formula
  
C5H10N2O3

Melting point
  
185 °C

Soluble in
  
Water

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Thermodynamic data
  
Phase behaviour solid–liquid–gas

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Glutamine (abbreviated as Gln or Q; encoded by the codons CAA and CAG) is an α-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.

Contents

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

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Functions

Glutamine plays a role in a variety of biochemical functions:

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  • Protein synthesis, as any other of the 20 proteinogenic amino acids
  • Lipid synthesis, especially by cancer cells.
  • Regulation of acid-base balance in the kidney by producing ammonium
  • Cellular energy, as a source, next to glucose
  • Nitrogen donation for many anabolic processes, including the synthesis of purines
  • Carbon donation, as a source, refilling the citric acid cycle
  • Nontoxic transporter of ammonia in the blood circulation
  • Precursor to the neurotransmitter glutamate
  • On the level of tissue, glutamine plays a role in maintaining the normal integrity of the intestinal mucosa.

    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. 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.

    Consumers

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    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.

    Nutrition

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    In states where tissue is being built or repaired, like growth of infants, or healing from traumtic wounds or severe illness, glutamine becomes conditionally essential.

    Occurrences in nature

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    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. 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.

    Dietary sources

    Humans obtain glutamine through catabolism of proteins in foods they eat.

    Research

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    Glutamine mouthwash may be useful to prevent oral mucositis in people undergoing chemotherapy but intravenous glutamine does not appear useful to prevent mucositis in the GI tract.

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    Glutamine supplementation was thought to have potential to reduce complications in people who are critically ill or who have had abdominal surgery but this was based on poor quality clinical trials; a large randomized clinical trial found worse outcomes in the group that was given glutamine.

    Supplementation does not appear to be useful in adults or children with Crohns disease or inflammatory bowel disease but clinical studies as of 2016 were underpowered.

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

    Medical food

    Several brands of glutamine are marketed as medical food and is prescribed when a medical professional believes a person in their care needs supplementary glutamine due to loss or deficiency of glutamine.

    References

    Glutamine Wikipedia