Global InformationGlutamine information
 Skeletal formula of L-glutamine
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| IUPAC name
Glutamine
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| Other names
L-Glutamine
(levo)glutamide 2,5-Diamino-5-oxopentanoic acid 2-Amino-4-carbamoylbutanoic acid Endari[1] | |||
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CAS Number
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3D model (JSmol)
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| Abbreviations | Gln, Q | ||
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| DrugBank |
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| ECHA InfoCard | 100.000.266 | ||
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PubChem CID
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CompTox Dashboard (EPA)
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InChI
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SMILES
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| Properties[2] | |||
Chemical formula
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C5H10N2O3 | ||
| Molar mass | 146.146 g·mol−1 | ||
| Melting point | decomposes around 185°C | ||
Solubility in water
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soluble | ||
| Acidity (pKa) | 2.2 (carboxyl), 9.1 (amino) | ||
Chiral rotation ([α]D)
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+6.5º (H2O, c = 2) | ||
| Pharmacology | |||
ATC code
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A16AA03 (WHO) | ||
| Supplementary data page | |||
| Glutamine (data page) | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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| Clinical data | |
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| Trade names | Endari, Nutrestore |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a617035 |
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| Routes of administration | By mouth |
| Drug class | Gastrointestinal agent |
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| ECHA InfoCard | 100.000.266 |
| Chemical and physical data | |
| Formula | C5H10N2O3 |
| Molar mass | 146.146 g·mol−1 |
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InChI
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| Glutamine (data page) | |
Glutamine (symbol Gln or Q)[4] 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.[5][6] It is encoded by the codons CAA and CAG. It is named after glutamic acid, which in turn is named after its discovery in cereal proteins, gluten.[7]
In human blood, glutamine is the most abundant free amino acid.[8]
The dietary sources of glutamine include 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, Brussels sprouts, celery, kale and fermented foods like miso.
The one-letter symbol Q for glutamine was assigned in alphabetical sequence to N for asparagine, being larger by merely one methylene –CH2– group. Note that P was used for proline, and O was avoided due to similarity with D. The mnemonic Qlutamine was also proposed.[7]
- ^ Cite error: The named reference
FDA2017Gluwas invoked but never defined (see the help page). - ^ Weast RC, ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: CRC Press. p. C-311. ISBN 0-8493-0462-8..
- ^ "Glutamine Use During Pregnancy". Drugs.com. 30 September 2019. Retrieved 23 April 2020.
- ^ "Nomenclature and Symbolism for Amino Acids and Peptides". IUPAC-IUB Joint Commission on Biochemical Nomenclature. 1983. Archived from the original on 9 October 2008. Retrieved 5 March 2018.
- ^ Food and Nutrition Board of the Institute of Medicine (2006). "Protein and Amino Acids". In Otten JJ, Hellwig JP, Meyers LD (eds.). Dietary Reference Intakes: The Essential Guide to Nutrient Requirements (PDF). Washington, D.C.: National Academies Press. p. 147. ISBN 978-0-309-10091-5. Archived from the original (PDF) on 9 March 2014.
- ^ Lacey JM, Wilmore DW (August 1990). "Is glutamine a conditionally essential amino acid?". Nutrition Reviews. 48 (8): 297–309. doi:10.1111/j.1753-4887.1990.tb02967.x. PMID 2080048.
- ^ a b Saffran M (April 1998). "Amino acid names and parlor games: from trivial names to a one-letter code, amino acid names have strained students' memories. Is a more rational nomenclature possible?". Biochemical Education. 26 (2): 116–118. doi:10.1016/s0307-4412(97)00167-2. ISSN 0307-4412.
- ^ Brosnan JT (June 2003). "Interorgan amino acid transport and its regulation". The Journal of Nutrition. 133 (6 Suppl 1): 2068S–2072S. doi:10.1093/jn/133.6.2068S. PMID 12771367.
