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Encyclopedia > Glutamine

Chemical structure of Glutamine
Chemical structure of the amino acid glutamine
Chemical structure of L-glutamine

Glutamine Image File history File links Glutamin_-_Glutamine. ... Image File history File links Size of this preview: 587 × 599 pixelsFull resolution‎ (724 × 739 pixels, file size: 25 KB, MIME type: image/png) File historyClick on a date/time to view the file as it appeared at that time. ...

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 N[C@@H](CCC(N)=O)C(O)=O
Complete data

Glutamine (abbreviated as Gln or Q; Glx or Z represents either glutamine 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 glutamate. Its codons are CAA and CAG. IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... PubChem is a database of chemical molecules. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... This article is about the chemistry of hydrogen. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, symbol, number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, period, block 16, 2, p Appearance colorless (gas) pale blue (liquid) Standard atomic weight 15. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Physical properties Hazard properties Chemical properties Pharmacological properties OrganicBox_complete References a  CID 738 from PubChem (Gln) a  CID 145815 from PubChem (D) a  CID 5961 from PubChem (L) ... Glutamic acid (Glu, E), is the protonated form of glutamate (the anion). ... This article is about the class of chemicals. ... For a non-technical introduction to the topic, see Introduction to Genetics. ... The term Side chain can have different meanings depending on the context: In chemistry and biochemistry a side chain is a part of a molecule attached to a core structure. ... Amide functional group Amides possess a conjugated system spread over the O, C and N atoms, consisting of molecular orbitals occupied by delocalized electrons. ... // Hydroxyl group The term hydroxyl group is used to describe the functional group -OH when it is a substituent in an organic compound. ... Glutamic acid (Glu, E), is the protonated form of glutamate (the anion). ... The general structure of an amine Amines are organic compounds and a type of functional group that contain nitrogen as the key atom. ... In organic chemistry, functional groups (or moieties) are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules. ... Amide functional group Amides possess a conjugated system spread over the O, C and N atoms, consisting of molecular orbitals occupied by delocalized electrons. ... Glutamate is the anion of glutamic acid. ...

Contents

Nutrition

Occurrences in nature

Glutamine is the most abundant naturally occurring, non-essential amino acid in the human body. 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. A top-down view of skeletal muscle Skeletal muscle is a type of striated muscle, usually attached to the skeleton. ...


Dietary sources

Food sources of glutamine include:

  • Animal sources: meat, fish, eggs, milk, yogurt, ricotta cheese, cottage cheese,
  • Plant sources: beans, spinach, parsley, cabbage. Small amounts of free L-glutamine are found in vegetable juices and fermented foods, such as miso [1]

Functions

  1. A substrate for DNA synthesis.
  2. Major role in protein synthesis.
  3. Primary source of fuel for enterocytes (cells lining the inside of the small intestine).
  4. Precursor for rapidly dividing immune cells, thus aiding in immune function.
  5. Regulation of acid-base balance in the kidney.[citation needed]
  6. Alternative source of fuel for the brain and helps to block cortisol-induced protein catabolism.
  7. As a form of fixed nitogen by heterocysts, exchanged for photosynthate from undifferentiated cyanobacterial cells.

Polar (uncharged) Enterocyte is a type of epithelial cell of the superficial layer of the small and large intestine tissue. ... Heterocysts are specialized nitrogen-fixing cells formed by some filamentous cyanobacteria, such as Nostoc punctiforme and Anabaena sperica, during nitrogen starvation. ... Orders The taxonomy is currently under revision. ...


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 patients (citation pending). 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. This article is about the sport of weightlifting. ... Professional Bodybuilder Gustavo Badell posing Bodybuilding is the process of maximizing muscle hypertrophy through the combination of weight training, sufficient caloric intake, and rest. ... The following is a list of sports, divided by category. ...


Aiding gastrointestinal function

There have been several recent studies into the effects of glutamine and what properties it possesses, and, there is now a significant body of evidence that links glutamine-enriched diets with intestinal effects; aiding maintenance of gut barrier function, intestinal cell proliferation and differentiation, as well as generally reducing septic morbidity and the symptoms of Irritable Bowel Syndrome. The reason for such "cleansing" properties is thought to stem from 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. [2] Enterocyte is a type of epithelial cell of the superficial layer of the small and large intestine tissue. ... Drawing of the structure of cork as it appeared under the microscope to Robert Hooke from Micrographia which is the origin of the word cell being used to describe the smallest unit of a living organism Cells in culture, stained for keratin (red) and DNA (green) The cell is the... The term cell growth is used in two different ways in biology. ... Cellular differentiation is a concept from developmental biology describing the process by which cells acquire a type. The morphology of a cell may change dramatically during differentiation, but the genetic material remains the same, with few exceptions. ... Gut redirects here. ...


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. [2]


Aiding recovery after surgery

It is also known that glutamine has various effects in reducing healing time after operations. Hospital waiting times after abdominal surgery are reduced by providing parenteral nutrition regimens containing amounts of glutamine to patients. Clinical trials have revealed that patients on supplementation regimens 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. [3] Wound healing, or wound repair, is the bodys natural process of regenerating dermal and epidermal tissue. ... “Surgeon” redirects here. ... Total parenteral nutrition (TPN), also called hyperalimentation, is the practice of feeding a person without using the gut. ... Leukotrienes are autocrine and paracrine eicosanoid lipid mediators derived from arachidonic acid by 5-lipoxygenase. ... Granulocytes are a category of white blood cells, characterised by the fact that all types have differently staining granules in their cytoplasm on light microscopy. ... A scanning electron microscope (SEM) image of a single human lymphocyte. ... Adverse effect, in medicine, is an abnormal, harmful, undesired and/or unintended side-effect, although not necessarily unexpected, which is obtained as the result of a therapy or other medical intervention, such as drug/chemotherapy, physical therapy, surgery, medical procedure, use of a medical device, etc. ...


See also

Many supplements come in capsule form. ... A dietary supplement is intended to supply nutrients, (vitamins, minerals, fatty acids or amino acids) that are missing or not consumed in sufficient quantity in a persons diet. ...

References

  1. ^ Glutamine. Vitamins & health supplements. Retrieved on November 1, 2007.
  2. ^ 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. Retrieved on 2007-11-01. 
  3. ^ 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. Retrieved on 2007-11-01. 
  4. ^ Jian, Z.M.; Cao, J.D.; Zhu, X.G.; Zhao, W.X.; Yu, J.C.; Ma, E.L.; Wang, X.R.; Zhu, M.W.; Shu, H.; Liu, Y.W. (1999). "The impact of alanyl-glutamine on clinical safety, nitrogen balance, intestinal permeability, and clinical outcome in postoperative patients: a randomized, double-blind, controlled study of 120 patients.". JPEN J Parenter Enteral Nutr 23 (5 Suppl): S62-6. Retrieved on 2007-11-01. 

[4] Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st century. ... is the 305th day of the year (306th in leap years) in the Gregorian calendar. ... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st century. ... is the 305th day of the year (306th in leap years) in the Gregorian calendar. ... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st century. ... is the 305th day of the year (306th in leap years) in the Gregorian calendar. ...


External links


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Analogues of nucleic acids: The 20 Common Amino Acids ("dp" = data page) Analogues of nucleic acids:
Alanine (dp) | Arginine (dp) | Asparagine (dp) | Aspartic acid (dp) | Cysteine (dp) | Glutamic acid (dp) | Glutamine (dp) | Glycine (dp) | Histidine (dp) | Isoleucine (dp) | Leucine (dp) | Lysine (dp) | Methionine (dp) | Phenylalanine (dp) | Proline (dp) | Serine (dp) | Threonine (dp) | Tryptophan (dp) | Tyrosine (dp) | Valine (dp)
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Dietary supplements
Types Amino acids • Bodybuilding supplement • Energy drink • Energy bar • Fatty acids • Herbal Supplements • Minerals • Probiotics • 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 • Dietary fiber • Elemental calcium • Ephedra • Fish oil • Folic acid • Ginseng • Glucosamine • Glutamine • Iron supplements • Japanese Honeysuckle • Krill oil • Lactobacillus • Lingzhi • Linseed oil • Red yeast rice • Royal jelly • Saw palmetto • Spirulina • Taurine • Wheatgrass • Wolfberry • Yohimbine • Zinc gluconate
Related articles Codex Alimentarius • Enzyte • Metabolife • Hadacol • Nutraceutical • Multivitamin

  Results from FactBites:
 
L-Glutamine (2338 words)
The amino acid L-glutamate is metabolized to L-glutamine in a reaction catalyzed by the enzyme glutamine synthase, a reaction which, in addition to L-glutamate, requires ammonia, ATP and magnesium.
Glutamine has been shown to be beneficial when administered in the form of glutamine peptides via TPN in some patients with varying forms of catabolic stress, e.g., some cancer, transplantation, intensive-care, surgical and immune-suppressed patients.
Benefits from enteral glutamine supplementation are generally less pronounced, but preliminary significant results have been reported with the use of oral glutamine in very-low-birth-weight infants and in some major trauma patients in whom glutamine seems to strengthen immunity, particularly in the gastrointestinal tract.
  More results at FactBites »


 

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