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Encyclopedia > Arginine
Skeletal structure of L-arginine

3D structure of L-arginine
Chemical structure of L-arginine

Arginine Image File history File links Arginin_-_Arginine. ... Image File history File links Size of this preview: 800 × 552 pixelsFull resolution (1003 × 692 pixel, file size: 37 KB, MIME type: image/png) Please see the file description page for further information. ...

Systematic (IUPAC) name
2-amino-5-(diaminomethylidene
amino)pentanoic acid
Identifiers
CAS number 74-79-3
PubChem         6322
Chemical data
Formula C6H14N4O2 
Molar mass 174.2 g/mol
SMILES N[C@@H](CCCNC(N)=N)C(O)=O
Complete data

Arginine (abbreviated as Arg or R)[1] is an α-amino acid. The L-form is one of the 20 most common natural amino acids. Its codons are CGU, CGC, CGA and CGG. In mammals, arginine is classified as a semiessential or conditionally essential amino acid, depending on the developmental stage and health status of the individual. Infants are unable to effectively synthesize arginine, making it nutritionally essential for infants. Adults, however, are able to synthesize arginine in the urea cycle. 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). ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... 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) very 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 Flash point - N/A R/S statement R: N/A S: N/A RTECS number: N/A Chemical properties Pharmacological properties OrganicBox_complete References a  EINECS number 205-866-5 ((-)-D-arginine hydrate) a  EINECS number 200-811-1 (for L-arginine) a  CID 71070 from PubChem... Phenylalanine is one of the standard amino acids. ... Optical isomerism is a form of isomerism (specifically stereoisomerism) where the two different isomers are the same in every way except being non-superposable mirror images of each other. ... RNA codons. ... The reactions of the urea cycle. ...


Arginine was first isolated from a lupin seedling extract in 1886 by the Swiss chemist Ernst Schulze. Species 150-200 species, including: Lupinus albus Lupinus angustifolius Lupinus luteus Lupinus albifrons Lupinus arboreus Lupinus arizonicus Lupinus bicolor Lupinus chamissonis Lupinus diffusus Lupinus excubitus Lupinus formosus Lupinus longifolius Lupinus microcarpus Lupinus mutabilis Lupinus nanus Lupinus nootkatensis Lupinus perennis Lupinus polyphyllus Lupinus sparsiflorus Lupinus sulphureus Lupinus texensis Lupinus tidestromii Lupinus...

Contents

Structure

Arginine can be to be a basic amino acid because the part of the side chain nearest to the backbone is long, carbon-containing and hydrophobic, whereas the end of the side chain is a complex guanidinium group. With a pKa of 12.48, the guanidinium group is positively charged in neutral, acidic and even most basic environments. Because of the conjugation between the double bond and the nitrogen lone pairs, the positive charge is delocalized. This group is able to form multiple H-bonds. 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. ... Guanidine is a crystalline compound of strong alkalinity formed by the oxidation of guanine. ... A chemically conjugated system, is a system of atoms covalently bonded with alternating single and double bonds (e. ... An example of a quadruple hydrogen bond between a self-assembled dimer complex reported by Meijer and coworkers. ...


Synthesis

Arginine is synthesized from citrulline by the sequential action of the cytosolic enzymes argininosuccinate synthetase (ASS) and argininosuccinate lyase (ASL). This is energetically costly, as the synthesis of each molecule of argininosuccinate requires hydrolysis of adenosine triphosphate (ATP) to adenosine monophosphate (AMP); i.e., two ATP equivalents. The chemical compound citrulline is an α-amino acid (AA). ... Argininosuccinate synthetase is an enzyme that participates in the urea cycle, which is a sequence of chemical reactions that takes place in the cells of the liver. ... ASL (argininosuccinate lyase) is a human gene that makes the protein argininosuccinate lyase, one of the enzymes controlling a series of reactions called the urea cycle. ... Adenosine 5-triphosphate (ATP) is a multifunctional nucleotide that is most important as a molecular currency of intracellular energy transfer. ... Adenosine monophosphate, also known as 5-adenylic acid and abbreviated AMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside adenosine. ...


Citrulline can be derived from multiple sources:

The pathways linking arginine, glutamine, and proline are bidirectional. Thus, the net utilization or production of these amino acids is highly dependent on cell type and developmental stage. Nitric oxide The nitric oxide synthase (NOS; EC 1. ... Ornithine is an amino acid, whose structure is: NH2-CH2-CH2-CH2-CHNH2-COOH Ornithine is one of the products of the action of the enzyme arginase on L-arginine, creating urea. ... Proline is an α-amino acid with the chemical formula HO2CCH(NH[CH2)3]. L-Proline is one of the twenty DNA-encoded amino acids. ... Glutamine is one of the 20 amino acids encoded by the standard genetic code. ... Glutamate is the anion of glutamic acid. ... Molecular structure of ADMA Asymmetric dimethylarginine (ADMA) is a naturally occurring chemical found in blood plasma. ... Glutamine is one of the 20 amino acids encoded by the standard genetic code. ... Proline is an α-amino acid with the chemical formula HO2CCH(NH[CH2)3]. L-Proline is one of the twenty DNA-encoded amino acids. ...


On a whole-body basis, synthesis of arginine occurs principally via the intestinal–renal axis, wherein epithelial cells of the small intestine, which produce citrulline primarily from glutamine and glutamate, collaborate with the proximal tubule cells of the kidney, which extract citrulline from the circulation and convert it to arginine, which is returned to the circulation. Consequently, impairment of small bowel or renal function can reduce endogenous arginine synthesis, thereby increasing the dietary requirement. In zootomy, epithelium is a tissue composed of a layer of cells. ... In biology the small intestine is the part of the gastrointestinal tract (gut) between the stomach and the large intestine and includes the duodenum, jejunum, and ileum. ... The chemical compound citrulline is an α-amino acid (AA). ... Glutamine is one of the 20 amino acids encoded by the standard genetic code. ... Glutamate is the anion of glutamic acid. ... The kidneys are organs that filter wastes (such as urea) from the blood and excrete them, along with water, as urine. ...


Synthesis of arginine from citrulline also occurs at a low level in many other cells, and cellular capacity for arginine synthesis can be markedly increased under circumstances that also induce iNOS. Thus, citrulline, a coproduct of the NOS-catalyzed reaction, can be recycled to arginine in a pathway known as the citrulline-NO or arginine-citrulline pathway. This is demonstrated by the fact that in many cell types, citrulline can substitute for arginine to some degree in supporting NO synthesis. However, recycling is not quantitative because citrulline accumulates along with nitrate and nitrite, the stable end-products of NO, in NO-producing cells.[2] Nitric oxide The nitric oxide synthase (NOS; EC 1. ...


Function

Arginine plays an important role in cell division, the healing of wounds, removing ammonia from the body, immune function, and the release of hormones. Arginine, taken in combination with proanthocyanidins[3] or yohimbine[4], has also been used as a treatment for erectile dysfunction. Proanthocyanidin (also known as OPC, pycno-genol, leukocyanidin and leucoanthocyanin) is a a class of bioflavonoids. ... Yohimbine, also known under the outdated names quebrachin, aphrodin, corynine, yohimvetol and hydroergotocin, is the principal alkaloid of the bark of the West-African tree Pausinystalia yohimbe Pierre (formerly Corynanthe yohimbe), family Rubiaceae (Madder family). ... Erectile dysfunction (ED) or impotence is a sexual dysfunction characterized by the inability to develop or maintain an erection of the penis. ...


In proteins

The geometry, charge distribution and ability to form multiple H-bonds make arginine ideal for binding negatively charged groups. For this reason arginine prefers to be on the outside of the proteins where it can interact with the polar environment. Incorporated in proteins, arginine can also be converted to citrulline by PAD enzymes. In addition, arginine can be methylated by protein methyltransferases. Methylation is a term used in the chemical sciences to denote the attachment or substitution of a methyl group on various substrates. ...


As a precursor

Arginine is the immediate precursor of NO, urea, ornithine and agmatine; is necessary for the synthesis of creatine; and can also be used for the synthesis of polyamines (mainly through ornithine and to a lesser degree through agmatine), citrulline, and glutamate. For being a precursor of NO, (relaxes blood vessels), arginine is used in many conditions where vasodilation is required. The presence of asymmetric dimethylarginine (ADMA), a close relative, inhibits the nitric oxide reaction; therefore, ADMA is considered a marker for vascular disease, just as L-arginine is considered a sign of a healthy endothelium. R-phrases , , , , S-phrases , , , Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references Nitric oxide or Nitrogen monoxide is a chemical compound with chemical formula NO. This gas is an important signaling molecule in the body of... For the use of creatine to enhance athletic performance, please see Creatine supplements. ... The blood vessels are part of the circulatory system and function to transport blood throughout the body. ... Molecular structure of ADMA Asymmetric dimethylarginine (ADMA) is a naturally occurring chemical found in blood plasma. ... It has been suggested that this article or section be merged with Coronary heart disease. ... The endothelium is the layer of thin, flat cells that lines the interior surface of blood vessels, forming an interface between circulating blood in the lumen and the rest of the vessel wall. ...


Implication in herpes simplex viral replication

Tissues culture studies have shown the suppression of viral replication when the lysine to arginine ratio in vitro favors lysine. The therapeutic consequence of this finding is unclear, but dietary arginine may affect the effectiveness of lysine supplementation.[5] Lysine is one of the 20 amino acids normally found in proteins. ...


Implication in contributing to risk of death from heart disease

A recent Johns Hopkins study testing the addition of L-arginine to standard postinfarction treatment has implicated L-arginine supplementation with an increased risk of death in patients recovering from heart attack.[6] This study has been discussed in some detail in : "Reverse Heart Disease Now" by Stephen T Sinatra MD and James C Roberts MD, publ. Wiley 2006 ISBN 0-471-74704-1 at pp 111 -113.


Growth hormone

Arginine increases the production of growth hormone.[7] Reports of its effects on male muscular development are not clearly proven. Growth hormone (GH) or somatotropin (STH) is a protein hormone which stimulates growth and cell reproduction in humans and other animals. ...


Prolactin

Although there haven't been thorough studies, some sources claim that arginine helps release prolactin, an estrogenic compound which is associated with lactation, and like all estrogenic compounds may curb the secretion of testosterone[citation needed]. Thus some bodybuilders stay away from pure arginine, intaking only amounts naturally found in protein. Prolactin (PRL) is a peptide hormone primarily associated with lactation. ...


Food sources

Arginine is found in chocolate, wheat germ and flour, buckwheat, granola, oatmeal, dairy products (cottage cheese, ricotta, nonfat dry milk, skim yogurt), beef (roasts, steaks), pork (bacon, ham), nuts (coconut, pecans, cashews, walnuts, almonds, Brazil nuts, hazel nuts, peanuts), seeds (pumpkin, sesame, sunflower), poultry (chicken and turkey light meat), wild game (pheasant, quail), seafood (halibut, lobster, salmon, shrimp, snails, tuna in water), chick peas, cooked soybeans[8], and some energy drinks. For other uses, see Chocolate (disambiguation). ... Wheat germ is the heart of the wheat kernel - a concentrated source of several essential nutrients including Vitamin E, folate (folic acid), phosphorus, thiamin, zinc and magnesium. ... Granola is a breakfast food and snack food consisting of rolled oats, nuts and honey which is baked until crispy. ... In the United States and Canada, oatmeal means any crushed oats, rolled oats, or cut oats used in recipes such as oatmeal cookies. ... A tub of cottage cheese Cottage cheese comes from chickens and is a cheese curd product with a mild flavor. ... Ricotta cheese is an Italian cheese made from the whey which results when making cheeses such as mozzarella or provolone. ... Powdered milk is a powder of a substance that when mixed with water creates a milk drink. ... For other uses, see Beef (disambiguation). ... For other uses, see Pork (disambiguation). ... For other uses, see Nut (disambiguation). ... This writeup is about biological seeds; for other meanings see Seed (disambiguation). ... This article does not cite any references or sources. ... Game is any animal hunted for food. ... Spaghetti with seafood (Spaghetti allo scoglio). ... Binomial name Pisum sativum A pea (Pisum sativum) is the small, edible round green seed which grows in a pod on a leguminous vine, hence why it is called a legume. ... Binomial name Glycine max Soybeans (US) or soya beans (UK) (Glycine max) are a high-protein legume (Family Fabaceae) grown as food for both humans and livestock. ... Energy drinks are beverages which contain legal stimulants, vitamins, and minerals, including caffeine, guarana, taurine, various forms of ginseng, maltodextrin, carnitine, creatine, and ginkgo biloba. ...


References

  1. ^ IUPAC-IUBMB Joint Commission on Biochemical Nomenclature. Nomenclature and Symbolism for Amino Acids and Peptides. Recommendations on Organic & Biochemical Nomenclature, Symbols & Terminology etc. Retrieved on 2007-05-17.
  2. ^ Image:Free review.png Enzymes of arginine metabolism J Nutr. 2004 Oct; 134(10 Suppl): 2743S-2747S; PMID 15465778 Free text
  3. ^ Stanislavov, R. and Nikolova. 2003. Treatment of Erectile Dysfunction with Pycnogenol and L-arginine. Journal of Sex and Marital Therapy, 29(3): 207 – 213.
  4. ^ Lebret, T., Hervéa, J. M., Gornyb, P., Worcelc, M. and Botto, H. 2002. Efficacy and Safety of a Novel Combination of L-Arginine Glutamate and Yohimbine Hydrochloride: A New Oral Therapy for Erectile Dysfunction. European Urology 41(6): 608-613.
  5. ^ Griffith RS, Norins AL, Kagan C. (1978). "A multicentered study of lysine therapy in Herpes simplex infection". Dermatologica. 156 (5): 257-267. PubMed. 
  6. ^ Arginine Therapy in Acute Myocardial Infarction JAMA. 2006 Jan; Vol.295 #1: 58-64; PMID 16391217 Abstract
  7. ^ Alba-Roth J, Müller O, Schopohl J, von Werder K (1988). "Arginine stimulates growth hormone secretion by suppressing endogenous somatostatin secretion". J Clin Endocrinol Metab 67 (6): 1186-9. PMID 2903866. 
  8. ^ L-Arginine Supplements Nitric Oxide Scientific Studies Food Sources. Retrieved on 2007-02-20.

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 137th day of the year (138th in leap years) in the Gregorian calendar. ... Image File history File links Free_review. ... 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 51st day of the year in the Gregorian calendar. ...

External links


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

  Results from FactBites:
 
Arginine - Wikipedia, the free encyclopedia (743 words)
Arginine can be considered to be an amphipathic amino acid as the part of the side chain nearest to the backbone is long, carbon-containing and hydrophobic, whereas the end of the side chain is a complex guanidinium group.
On a whole-body basis, synthesis of arginine occurs principally via the intestinal–renal axis, wherein epithelial cells of the small intestine, which produce citrulline primarily from glutamine and glutamate, collaborate with the proximal tubule cells of the kidney, which extract citrulline from the circulation and convert it to arginine, which is returned to the circulation.
Arginine is the immediate precursor of NO, urea, ornithine and agmatine; is necessary for the synthesis of creatine; and can be used for the synthesis of polyamines (mainly through ornithine and to a lesser degree through agmatine), citrulline, and glutamate.
  More results at FactBites »

 
 

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