Alanyl-glutamine

Alanyl-glutamine is a chemical compound which in the form L-alanyl-L-glutamine is used in dietary supplementation, in parenteral nutrition, and in cell culture. It is a dipeptide consisting of alanine and glutamine.[1][2]

Alanyl-glutamine
Names
IUPAC name
L-Alanyl-L-glutamine
Identifiers
3D model (JSmol)
Abbreviations Ala-Gln
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.129.824
EC Number
  • 609-717-9
KEGG
UNII
  • InChI=1S/C8H15N3O4/c1-4(9)7(13)11-5(8(14)15)2-3-6(10)12/h4-5H,2-3,9H2,1H3,(H2,10,12)(H,11,13)(H,14,15)/t4-,5-/m0/s1
  • CC(C(=O)NC(CCC(=O)N)C(=O)O)N
  • C[C@@H](C(=O)N[C@@H](CCC(=O)N)C(=O)O)N
Properties
C8H15N3O4
Molar mass 217.225 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Dieterary supplement

As a dietary supplement, alanyl-glutamine protects the gastrointestinal tract.[3][4][5] The protective effect reduces bacterial translocation, thus reducing the risk of infections and infection-related problems such as diarrhea, dehydration, malabsorption, and electrolyte imbalance.[2]

Parenteral nutrition

At room temperature with 1 atmosphere of pressure, L-alanyl-L-glutamine has a solubility of about 586 g/L, which is more than 10 times glutamine's solubility (35 g/L). Also, glutamine does not withstand sterilization procedures, whereas alanyl-glutamine does. Alanyl-glutamine's high solubility makes it valuable in parenteral nutrition.[6][7]

Cell culture

In cell culture, L-alanyl-L-glutamine is sometimes used as a replacement for L-glutamine because this dipeptide is stable in aqueous solution unlike L-glutamine which spontaneously degrades to form ammonia and pyrrolidine carboxylic acid. During cell culture, L-alanyl-L-glutamine is broken down into L-glutamine which is an essential nutrient for the cells. Because the chemical compound L-alanyl-L-glutamine is broken down a little at a time, the cells have time to use the L-glutamine that is formed before it is broken down into ammonia and pyrrolidine carboxylic acid. Ammonia tends to damage the cells, which means that when growing with a medium that uses L-glutamine instead of L-alanyl-L-glutamine, it is necessary to change the cells' growth medium more often.[8][9]

L-Alanyl-L-glutamine is sold under the name GlutaMAX by Thermo Fisher Scientific[10] and under the name AminoStable by Ajinomoto.[11]

References
  1. PubChem. "l-Alanyl-l-glutamine". pubchem.ncbi.nlm.nih.gov.
  2. "NCI Thesaurus". ncit.nci.nih.gov.
  3. Lima, Noélia L.; Soares, Alberto M.; Mota, Rosa MS; Monteiro, Helena SA; Guerrant, Richard L.; Lima, Aldo AM (2007). "Wasting and Intestinal Barrier Function in Children Taking Alanyl-Glutamine–Supplemented Enteral Formula". Journal of Pediatric Gastroenterology & Nutrition. 44 (3): 365–374. doi:10.1097/MPG.0b013e31802eecdd. PMID 17325559. S2CID 44575071.
  4. Zou, T.D.; Deng, C.X.; Wang, Z.R.; Ye, Y.L.; You, J.M. (2019). "Dietary alanyl-glutamine improves growth performance of weaned piglets through maintaining intestinal morphology and digestion–absorption function". Animal. 13 (9): 1826–1833. doi:10.1017/S1751731119000223. PMID 30789107. S2CID 73470476.
  5. Xing, Shen; Zhang, Bolin; Lin, Meng; Zhou, Ping; Li, Jiaolong; Zhang, Lin; Gao, Feng; Zhou, Guanghong (2016). "Effects of alanyl-glutamine supplementation on the small intestinal mucosa barrier in weaned piglets". Asian-Australasian Journal of Animal Sciences. 30 (2): 236–245. doi:10.5713/ajas.16.0077. PMC 5205612. PMID 27383799.
  6. Fürst, Peter; Pogan, Karin; Stehle, Peter (1997). "Glutamine dipeptides in clinical nutrition". Nutrition. 13 (7–8): 731–737. doi:10.1016/S0899-9007(97)83035-3. PMID 9263278.
  7. Luo, Menghua; Fernandez-Estivariz, Concepcion; Jones, Dean P.; Accardi, Carolyn R.; Alteheld, Birgit; Bazargan, Niloofar; Hao, Li; Griffith, Daniel P.; Blumberg, Jeffrey B.; Galloway, John R.; Ziegler, Thomas R. (2008). "Depletion of plasma antioxidants in surgical intensive care unit patients requiring parenteral feeding: Effects of parenteral nutrition with or without alanyl-glutamine dipeptide supplementation". Nutrition. 24 (1): 37–44. doi:10.1016/j.nut.2007.10.004. PMC 2712494. PMID 18065204.
  8. "L-Glutamine & GlutaMAX Supplement - US". www.thermofisher.com.
  9. Zhao, Ming-Hui; Kim, Nam-Hyung; Cui, Xiang-Shun (2016). "GlutaMAX prolongs the shelf life of the culture medium for porcine parthenotes". Theriogenology. 85 (3): 368–375. doi:10.1016/j.theriogenology.2015.08.014. PMID 26462658.
  10. "GlutaMAX™ Supplement". www.thermofisher.com.
  11. "L-Alanyl-L-Glutamine Amino Acid (Ala-Gln)". www.bioprocessonline.com. Archived from the original on 2021-11-13. Retrieved 2021-11-14.
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