Difference between revisions of "Glutamine" - New World Encyclopedia

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'''Glutamine''' (Gln, Q) is one of the 20 [[amino acid]]s encoded by the standard [[genetic code]]. Its [[side chain]] is an [[amide]]; it is formed by replacing a side-chain [[hydroxyl]] of [[glutamic acid]] with an [[amine]] [[functional group]].
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'''Glutamine''' is an α-[[amino acid]] that is found in many [[protein]]s and is a neutralized version of the acidic amino acid [[glutamic acid]], having an [[amide]] side chain that is formed by replacing a side-chain [[hydroxyl]] of glutamic acid with an [[amine]] functional group. Glutamine is the most abundant amino acid in [[human being]]s (Longe 2005). It is important in many [[metabolism|metabolic]] processes, in the elimination of toxic ammonia from the body, and in [[immune system|immunity]], as well as a nutritional supplement in treating a variety of [[disease]]s.
  
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The L-isomer, which is the only form that is involved in protein synthesis, is one of the 20 [[amino acid#standard amino acid|standard amino acids]] common in animal proteins and required for normal functioning in humans. However, it is not considered to be an [[amino acid#essential amino acid|"essential" amino acid]] since it does not have to be taken in with the diet, but can be synthesized by the human body from other compounds through chemical reactions. It is essential in the diet of premature infants, however, who cannot produce glutamine fast enough.
  
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Neutralized version of glutamic acid. Used in proteins and as a storage for ammonia
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STRESS
  
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'''Glutamic acid''',  also referred to as '''glutamate''' (the [[salt]] of glutamic acid), is an acidic, α-[[amino acid]] that is found in many [[protein]]s, and that in free form functions as an important [[neurotransmitter]], a metabolic intermediate in the [[Krebs cycle]], and a compound that can combine with an help in the elimination of toxic ammonia from the body. The salt monosodium glutamate (MSG) is a common food additive and flavor enhancer. Along with [[aspartic acid]], to which is behaves similarly, glutamic acid is classified as an acidic amino acid.
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Glutamine's three letter code is Gln, its one letter code is Q, and its systematic name is 2-Amino-4-carbamoylbutanoic acid(IUPAC-IUB 1983). A three-letter designation for either glutamine (Gln) or glutamic acid (Glu) is '''Glx'''—this is often used in cases in which peptide sequencing reactions may convert glutamine to glutamate (or vice versa), leaving the original identity of the amino acid in doubt.
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The L-isomer, which is the only form that is involved in protein synthesis, is one of the 20 [[amino acid#standard amino acid|standard amino acids]] common in animal proteins and required for normal functioning in humans. However, it is not considered to be an [[amino acid#essential amino acid|"essential" amino acid]] since it does not have to be taken in with the diet, but can be synthesized by the human body from other compounds through chemical reactions.
 
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Glutamic acid is responsible for one of the human senses of [[taste]], termed ''umami'', adding to the classical taste sensations of sweet, salty, sour, and bitter. Umami applies to the sensation of savoriness, the detection of glutamates in such foods as meats, cheese, and other protein-heavy foods. Beyond its practical value, taste adds to the human enjoyment of creation, joining such diverse senses as being able to see various colors, hear different sounds, [[olfaction|smell]] a vast array of odors, and so forth. Such senses allow interaction with nature and touch upon the inner aspect of people. As a source for umami, MSG, the sodium salt of glutamic acid, is used to enhance the flavor of foods.
 
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Glutamic acid's three letter code is Glu, its one letter code is E, and its systematic name is 2-Aminopentanedioic acid(IUPAC-IUB 1983). A three-letter designation for either glutamic acid (Glu) or the amino acid [[glutamine]] (Gln) is '''Glx'''—this is often used in cases in which peptide sequencing reactions may convert glutamine to glutamate (or vice versa), leaving the original identity of the amino acid in doubt.
 
  
 
==Structure==
 
==Structure==
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H2N-CO-[CH2]2-CH(NH2)-COOH
  
  

Revision as of 00:37, 27 June 2007

Chemical structure of GlutamineChemical 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 
Mol. weight 146.15
SMILES N[C@@H](CCC(N)=O)C(O)=O
Complete data


Glutamine is an α-amino acid that is found in many proteins and is a neutralized version of the acidic amino acid glutamic acid, having an amide side chain that is formed by replacing a side-chain hydroxyl of glutamic acid with an amine functional group. Glutamine is the most abundant amino acid in human beings (Longe 2005). It is important in many metabolic processes, in the elimination of toxic ammonia from the body, and in immunity, as well as a nutritional supplement in treating a variety of diseases.

The L-isomer, which is the only form that is involved in protein synthesis, is one of the 20 standard amino acids common in animal proteins and required for normal functioning in humans. However, it is not considered to be an "essential" amino acid since it does not have to be taken in with the diet, but can be synthesized by the human body from other compounds through chemical reactions. It is essential in the diet of premature infants, however, who cannot produce glutamine fast enough.

STRESS

Glutamine's three letter code is Gln, its one letter code is Q, and its systematic name is 2-Amino-4-carbamoylbutanoic acid(IUPAC-IUB 1983). A three-letter designation for either glutamine (Gln) or glutamic acid (Glu) is Glx—this is often used in cases in which peptide sequencing reactions may convert glutamine to glutamate (or vice versa), leaving the original identity of the amino acid in doubt.

Structure

In biochemistry, the term amino acid is frequently used to refer specifically to alpha amino acids: those amino acids in which the amino and carboxylate groups are attached to the same carbon, the so-called α–carbon (alpha carbon). The general structure of these alpha amino acids is: 

     R
     |
 H2N-C-COOH
     |
     H

where R represents a side chain specific to each amino acid.

Most amino acids occur in two possible optical isomers, called D and L. The L amino acids represent the vast majority of amino acids found in proteins. They are called proteinogenic amino acids. As the name "proteinogenic" (literally, protein building) suggests, these amino acid are encoded by the standard genetic code and participate in the process of protein synthesis. In glutamic acid, only the L-stereoisomer is involved in protein synthesis in mammals.

Glutamic acids chemical formula is HOOC-CH(NH2)-(CH2)2-COOH (very similar to aspartic acid's formula, HOOC-CH(NH2)-CH2-COOH), but with an extra CH2), or more generally C5H9NO4. (Aspartic acid's general forumula is C4H7NO4.)


H2N-CO-[CH2]2-CH(NH2)-COOH


Biochemistry

Formation and Nomenclature

Glutamine is genetically coded for by the RNA codons CAA and CAG. Glutamine's three-letter abbreviation is Gln, and its one-letter abbreviation is Q. A three-letter designation for either glutamine or glutamic acid is Glx (one-letter abbreviation: Z).

Like other amino acids, glutamine is biochemically important as a constituent of proteins. Glutamine is also crucial in nitrogen metabolism. Ammonia (formed by nitrogen fixation) is assimilated into organic compounds by converting glutamic acid to glutamine. The enzyme that accomplishes this is called glutamine synthetase. Glutamine can, hence, be used as a nitrogen donor in the biosynthesis of many compounds, including other amino acids, purines, and pyrimidines.

Artificial glutamine synthesis was first reported in 1933 in the Bergmann-Zervas carbobenzoxy method [1]

Nutrition

Occurrences in Nature

Glutamine is found in foods high in proteins, such as fish, red meat, beans, and dairy products.

Use

Glutamine is a supplement that is used in weightlifting, bodybuilding, endurance and other sports, as well as by those who suffer from muscular cramps or pain—particularly elderly people. The main use of glutamine within the diet of either group is as a means of replenishing the body's supply of amino acids that have been used during exercise or everyday activities.

Studies which are looking into problems with excessive consumption of glutamine thus far have proved inconclusive. Normal supplementation is healthy mainly because glutamine is helpful after prolonged periods of exercise (for example, a workout or exercise in which amino acids are required for use) and replenishes amino acid supply; this being the main reason glutamine is recommended during fasting or for people who suffer from physical trauma, immune deficiencies, or cancer.[2] A secondary benefit to bettering body immunity is fortification of the intestinal tract, responsible for roughly 70% of the body's immunity.

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. Template:Ref N

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. Template:Ref N

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. Template:Ref N

See also

  • Bodybuilding supplements
  • Dietitian

References
ISBN links support NWE through referral fees

  1. ↑ Bergmann, M., Zervas, L., and Salzmann, L., Ber. them. Ges., 99, 1233 (1933).
  2. ↑ Glutamine used for the Immune System and Cancer. Retrieved 2006-07-28.
  1. Template:Note N Template:Note N File:Free text.png Boza J.J., Dangin M., Moennoz D., Montigon F., Vuichoud J., Jarret A., Pouteau E., Gremaud G., Oguey-Araymon S., Courtois D., Woupeyi A., Finot P.A. and Ballevre O. Free and protein-bound glutamine have identical splanchnic extraction in healthy human volunteers. Am J Physiol Gastrointest Liver Physiol. 2001 Jul; 281(1): G267-74. PMID 11408280 Free text
  2. Template:Note N McAnena O.J., Moore F.A., Moore E.E., Jones T.N. and Parsons P. Selective uptake of glutamine in the gastrointestinal tract: confirmation in a human study. Br J Surg. 1991 Apr; 78(4): 480-2. PMID 1903318
  3. Template:Note N Morlion B.J., Stehle P., Wachtler P., Siedhoff H.P., Koller M., Konig W., Furst P., Puchstein C. Total parenteral nutrition with glutamine dipeptide after major abdominal surgery. Ann Surg. 1998 Feb; 227(2): 302-8. PMID 9488531
  4. Template:Note N Jiang 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. The impact of alanyl-glutamine on clinical safety, nitrogen balance, intestinal permeability, and clinical outcome in postoperative patients: a randomised, double-blind, controlled study of 120 patients. JPEN J Parenter Enteral Nutr. 1999 Sep-Oct;23(5 Suppl):S62-6. PMID 10483898

External links

Template:ChemicalSources


Major families of biochemicals
Peptides | Amino acids | Nucleic acids | Carbohydrates | Nucleotide sugars | Lipids | Terpenes | Carotenoids | Tetrapyrroles | Enzyme cofactors | Steroids | Flavonoids | Alkaloids | Polyketides | Glycosides
Analogues of nucleic acids:The 20 Common Amino AcidsAnalogues 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)
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

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