Alanyl-glutamine is a chemical compound which in the form <small>L</small>-alanyl-<small>L</small>-glutamine is used in dietary supplementation, in parenteral nutrition, and in cell culture. It is a dipeptide consisting of alanine and glutamine.
As a dietary supplement, alanyl-glutamine protects the gastrointestinal tract. The protective effect reduces bacterial translocation, thus reducing the risk of infections and infection-related problems such as diarrhea, dehydration, malabsorption, and electrolyte imbalance.
At room temperature with 1 atmosphere of pressure, <small>L</small>-alanyl-<small>L</small>-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.
In cell culture, <small>L</small>-alanyl-<small>L</small>-glutamine is sometimes used as a replacement for <small>L</small>-glutamine because this dipeptide is stable in aqueous solution unlike <small>L</small>-glutamine which spontaneously degrades to form ammonia and pyrrolidone carboxylic acid. During cell culture, <small>L</small>-alanyl-<small>L</small>-glutamine is broken down into <small>L</small>-glutamine which is an essential nutrient for the cells. Because the chemical compound <small>L</small>-alanyl-<small>L</small>-glutamine is broken down a little at a time, the cells have time to use the <small>L</small>-glutamine that is formed before it is broken down into ammonia and pyrrolidone carboxylic acid. Ammonia tends to damage the cells, which means that when growing with a medium that uses <small>L</small>-glutamine instead of <small>L</small>-alanyl-<small>L</small>-glutamine, it is necessary to change the cells' growth medium more often.
<small>L</small>-Alanyl-<small>L</small>-glutamine is sold under the name GlutaMAX by Thermo Fisher Scientific and under the name AminoStable by Ajinomoto.