Glutamine

Names IUPAC nameSystematic IUPAC nameOther names Identifiers Abbreviations Gln, QChEBIChEMBLChemSpiderDrugBankECHA InfoCard100.000.266EC NumberKEGGUNIIProperties C₅H₁₀N₂O₃Molar mass146.146 g·mol Melting pointdecomposes around 185°C soluble Acidity (pK_a) 2.2 (carboxyl), 9.1 (amino) +6.5º (H₂O, c = 2) Pharmacology A16AA03 (WHO) Supplementary data page Glutamine (data page)

Glutamine (symbol Gln or Q) 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. 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.

In human blood, glutamine is the most abundant free amino acid.

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.