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16-September-2008 20:42:47 - Glutamine Chemical structure of Glutamine Chemical structure of the amino acid glutamine Chemical structure of L-glutamine Glutamine Systematic IUPAC name 2S-2-amino-4-carbamoyl-butanoic acid Identifiers CAS number 56-85-9 PubChem 738 Chemical data Formula C5H10N2O3 Molar mass 146.15 g/mol SMILES NC@@HCCCN=OCO=O Complete data Glutamine abbreviated as Gln or Q; the abbreviation Glx or Z represents either glutamate or glutamic acid is one of the 20 amino acids encoded by the standard genetic code. Its side chain is an amide formed by replacing the side-chain hydroxyl of glutamic acid with an amine functional group. It can therefore be considered the amide of the acidic amino acid glutamic acid. Its codons are CAA and CAG. Contents 1 Nutrition 1.1 Occurrences in nature 1.1.1 Dietary sources 1.2 Functions 1.3 Use 1.4 Aiding gastrointestinal function 1.5 Aiding recovery after surgery 2 References 3 External links Nutrition Occurrences in nature Glutamine is the most abundant naturally occurring, non-essential amino acid in the human body and one of the only amino acids which directly crosses the blood-brain barrier1. In the body it is found circulating in the blood as well as stored in the skeletal muscles. It becomes conditionally essential requiring intake from food or supplements in states of illness or injury. Dietary sources Dietary sources of L-glutamine include beef, chicken, fish, eggs, milk, dairy products, cabbage, beets, beans, spinach, and parsley. Small amounts of free L-glutamine are also found in vegetable juices and fermented foods, such as miso.2 Functions Glutamine has a variety of biochemical functions including: A substrate for DNA synthesis Major role in protein synthesis Primary source of fuel for enterocytes cells lining the inside of the small intestine. Precursor for rapidly dividing immune cells, thus aiding in immune function Regulation of acid-base balance in the kidney by producing ammonium3 Alternative source of fuel for the brain and helps to block cortisol-induced protein catabolism As a form of fixed nitogen by heterocysts, exchanged for photosynthate from undifferentiated cyanobacterial cells Use In catabolic states of injury and illness, GLN becomes conditionally-essential requiring intake from food or supplements. Glutamine has been studied extensively over the past 10-15 years and has been shown to be useful in treatment of serious illnesses, injury, trauma, burns, cancer and its treatment related side-effects as well as in wound healing for postoperative patients4. That is why it is now also classified as a nutraceutical. Glutamine is also marketed as a supplement used for muscle growth in weightlifting, bodybuilding, endurance and other sports.5 It is also used to reduce muscle wasting in patients with cancer and AIDS6. Glutamine has also been taken to enhance brain function as it fuels two of the brain's most important neurotransmitters: glutamic acid and gamma-aminobutyric acid GABA. It also assists in nitrogen transportation and reduces toxic build up of ammonia in the brain though is contra-indicated for those with Reye's Syndrome. Hence, it has been used to aid memory, increase IQ in those with mental retardation, used to support those with schizophrenia and senility7. It has also been used in the treatment of ADHD, anxiety 8 and depression910. It has also been used in recovery programs to break sugar craving cycles in alchoholics although is contra-indicated for those with cirrhosis of the liver or kidney diseaseand assist people in the management of sugar craving in diabetes1112. It is also used as an anti-inflammatory in the treatment of autoimmune diseases and preserves Glutathione important for detoxification and immune support levels in the liver13. Glutamine is contraindicated for those with Reye's Disease, cirrhosis of the liver and kidney disease14. Aiding gastrointestinal function In recent studies, glutamine-enriched diets have been linked with intestinal effects including maintenance of gut barrier function15, intestinal cell proliferation and differentiation16. It may be used in recovery after gut surgery or in the treatment of gut damage17, the treatment of sepsis18 and irritable bowel syndrome19. This may relate to the fact that the intestinal extraction rate of glutamine is higher than that for other amino acids, and is therefore thought to be the most viable option when attempting to alleviate conditions relating to the gastrointestinal tract. 20 These conditions were discovered after comparing plasma concentration within the gut between glutamine-enriched and non glutamine-enriched diets. However, even though glutamine is thought to have cleansing properties and effects, it is unknown to what extent glutamine has clinical benefits, due to the varied concentrations of glutamine in varieties of food. 20 Aiding recovery after surgery It is also known that glutamine has various effects in reducing healing time after operations. Hospital-stay times after abdominal surgery can be reduced by providing parenteral nutrition regimes containing high amounts of glutamine to patients. Clinical trials have revealed that patients on supplementation regimes containing glutamine have improved nitrogen balances, generation of cysteinyl-leukotrienes from polymorphonuclear neutrophil granulocytes and improved lymphocyte recovery and intestinal permeability in postoperative patients - in comparison to those who had no glutamine within their dietary regime; all without any side-effects. 21 References ^ Template:Http://ajpcell.physiology.org/cgi/content/full/274/4/C1101 ^ Glutamine. Vitamins health supplements. Retrieved on November 1, 2007. ^ Textbook of Medical Physiology Guyton Hall 11th ion, p. 393 ^ Template:Http://www.cfsn.com/ibs.html ^ John Ivy and Portman, Robert, Nutrient Timing,Laguna Beach: Basic Health Publications, 2004, page 57. ^ Template:Cirrhosis ^ Template:Http://www.experiencelifemag.com/issues/november-december-2002/health-wellness/glutamine.html ^ Template:Http://www.neurogenesis.com/Amino-Acids/glutamine.php ^ Template:Http://www.naturalhealthweb.com/articles/esparza1.html ^ Template:Http://intelegen.com/nutrients/add.htm ^ Template:Http://www.sundancevideoonline.com/glutamine.html ^ Template:Http://www.experiencelifemag.com/issues/november-december-2002/health-wellness/glutamine.html ^ Template:Http://www.sundancevideoonline.com/glutamine.html ^ Template:Http://www.naturalhealthtechniques.com/diet nutrition/amino acid list1.htm ^ Template:Http://www.nutri-notes.com/marapr98 simple.htm ^ Template:Http://findarticles.com/p/articles/mi qa3762/is 199905/ai n8828316 ^ Template:Http://findarticles.com/p/articles/mi qa3762/is 199905/ai n8828316 ^ Template:Http://ajpregu.physiology.org/cgi/content/abstract/292/5/R1839?rss=1 ^ Template:Http://www.cfsn.com/ibs.html ^ a b Boza, J.J.; Dangin, M.; Moennoz, D.; Montigon, F.; Vuichoud, J.; Jarret, A.; Pouteau, E.; Gremaud, G.; Oguey-araymon, S.; Courtois, D.; Others, 2001. Free and protein-bound glutamine have identical splanchnic extraction in healthy human volunteers. American Journal of Physiology- Gastrointestinal and Liver Physiology 281 1: 267-274. doi:10.1097/00000658-199802000-00022. PMID 11408280. Retrieved on 2007-11-01. ^ Morlion, B.J.; Stehle, P.; Wachtler, P.; Siedhoff, H.P.; Koller, M.; Konig, W.; Furst, P.; Puchstein, C. 1998. Total parenteral nutrition with glutamine dipeptide after major abdominal surgery: a randomized, double-blind, controlled study. Ann Surg 227 2: 302-8. doi:10.1097/00000658-199802000-00022. Retrieved on 2007-11-01. 1 External links Glutamine details, treatment benefits and precautions Computational Chemistry Wiki Nutrients and HIV: Part Three Supplemental uses v d e The 20 Common Amino Acids dp = data page Branched-chain amino acids Isoleucine dp | Leucine dp | Valine dp Non Branch-chain Alanine dp | Arginine dp | Asparagine dp | Aspartic acid dp | Cysteine dp | Glutamic acid dp | Glutamine dp | Glycine dp | Histidine dp | Lysine dp | Methionine dp | Phenylalanine dp | Proline dp | Serine dp | Threonine dp | Tryptophan dp | Tyrosine dp Other classifications Essential amino acids | Ketogenic amino acid | Glucogenic amino acid Major families of biochemicals Saccharides | Carbohydrates | Glycosides | | Amino acids | Peptides | Proteins | Glycoproteins | | Lipids | Terpenes | Steroids | Carotenoids Alkaloids | Nucleobases | Nucleic acids | | Enzyme cofactors | Flavonoids | Polyketides | Tetrapyrroles v d e Dietary supplements Types Amino acids Bodybuilding supplement Energy drink Energy bar Fatty acids Herbal Supplements Minerals Prebiotics Probiotics Lactobacillus, Bifidobacterium Vitamins Whole food supplements Vitamins and minerals Retinol Vitamin A B vitamins: Thiamine B1 Riboflavin B2 Niacin B3 Pantothenic acid B5 Pyridoxine B6 Biotin B7 Folic acid B9 Cyanocobalamin B12 Ascorbic acid Vitamin C Ergocalciferol and Cholecalciferol Vitamin D Tocopherol Vitamin E Naphthoquinone Vitamin K Calcium Choline Chlorine Chromium Cobalt Copper Fluorine Iodine Iron Magnesium Manganese Molybdenum Phosphorus Potassium Selenium Sodium Sulfur Zinc Other common ingredients Carnitine Chondroitin sulfate Cod liver oil Copper gluconate Creatine/Creatine supplements Dietary fiber Elemental calcium Ephedra Fish oil Folic acid Ginseng Glucosamine Glutamine Iron supplements Japanese Honeysuckle Krill oil Lingzhi Linseed oil Melatonin Red yeast rice Royal jelly Saw palmetto Spirulina Taurine Wheatgrass Wolfberry Yohimbine Zinc gluconate Related articles Codex Alimentarius Enzyte Metabolife Hadacol Nutraceutical Multivitamin Nutrition Retrieved from http://en..org/wiki/Glutamine Categories: Proteinogenic amino acids | Dietary supplements | Glucogenic amino acids Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Català Česky Deutsch Español Esperanto Français í•œêµì–´ Bahasa Indonesia Italiano עברית LatvieÅ¡u Lëtzebuergesch Lietuvių Nederlands 日本語 ‪Norsk bokmÃ¥l‬ Polski Português РуÑ?Ñ?кий SlovenÄ?ina СрпÑ?ки / Srpski Suomi Svenska Türkçe УкраїнÑ?ька ä¸æ–‡ This page was last modified on 4 August 2008, at 17:58
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