Alanyl-glutamine
Chemical compound From Wikipedia, the free encyclopedia
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]
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| IUPAC name
L-Alanyl-L-glutamine | |
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3D model (JSmol) |
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| Abbreviations | Ala-Gln |
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| DrugBank | |
| ECHA InfoCard | 100.129.824 |
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| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| 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).
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Dietary 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.[citation needed] 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
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