Glutamine

L-glutamine oral powder
Clinical data
Trade names	Endari, Nutrestore
AHFS/Drugs.com	Monograph
MedlinePlus	a617035
License data	US DailyMed: Glutamine;
Routes of; administration	By mouth
Drug class	Gastrointestinal agent
ATC code	A16AA03 (WHO) ;
Legal status
Legal status	US: ℞-only;
Identifiers
	IUPAC name (S)-2,5-diamino-5-oxopentanoic acid;
CAS Number	56-85-9;
PubChem CID	5961;
DrugBank	DB00130;
ChemSpider	5746;
UNII	0RH81L854J;
KEGG	D00015; C00064;
ChEBI	CHEBI:58359;
ChEMBL	ChEMBL930;
PDB ligand	GLN (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID1023100 ;
ECHA InfoCard	100.000.266
Chemical and physical data
Formula	C5H10N2O3
Molar mass	146.146 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C(CC(=O)N)C(C(=O)O)N;
	InChI InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m0/s1; Key:ZDXPYRJPNDTMRX-VKHMYHEASA-N;
Data page
	Glutamine (data page)

Glutamine
	; Skeletal formula of L-glutamine
Ball-and-stick model	Space-filling model
Names
	IUPAC name Glutamine
	Other names L-Glutamine ; (levo)glutamide ; 2,5-Diamino-5-oxopentanoic acid ; 2-Amino-4-carbamoylbutanoic acid; Endari
Identifiers
CAS Number	56-85-9 ;
3D model (JSmol)	Interactive image; Zwitterion: Interactive image;
Abbreviations	Gln, Q
ChEBI	CHEBI:18050 ;
ChEMBL	ChEMBL930 ;
ChemSpider	5746 ;
DrugBank	DB00130 ;
ECHA InfoCard	100.000.266
EC Number	200-292-1;
IUPHAR/BPS	723;
KEGG	C00303 ;
PubChem CID	5961;
UNII	0RH81L854J ;
CompTox Dashboard (EPA)	DTXSID1023100 ;
	InChI InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m0/s1 Key: ZDXPYRJPNDTMRX-VKHMYHEASA-N ;
	SMILES O=C(N)CCC(N)C(=O)O; Zwitterion: O=C(N)CCC([NH3+])C(=O)[O-];
Properties
Chemical formula	C5H10N2O3
Molar mass	146.146 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
	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

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 FDA2017Glu was 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.

[FDA2017Glu-1] Cite error: The named reference FDA2017Glu was invoked but never defined (see the help page).

[2] 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..

[Drugs.com_preganancy-3] "Glutamine Use During Pregnancy". Drugs.com. 30 September 2019. Retrieved 23 April 2020.

[4] "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.

[5] 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.

[6] 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.

[Saffran_1998-7] 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-8] 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.

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