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20-September-2008 09:55:59 - Arginine Skeletal structure of L-arginine 3D structure of L-arginine Chemical structure of L-arginine Arginine Systematic IUPAC name 2-amino-5-diaminomethylidene aminopentanoic acid Identifiers CAS number 74-79-3 PubChem 6322 Chemical data Formula C6H14N4O2 Molar mass 174.2 g/mol SMILES NC@@HCCCNCN=NCO=O Complete data Arginine abbreviated as Arg or R1 is an α-amino acid. The L-form is one of the 20 most common natural amino acids. Its codons are CGU, CGC, CGA, CGG, AGA, and AGG. 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 meet their requirements and thus arginine is nutritionally essential for infants. Arginine was first isolated from a lupin seedling extract in 1886 by the Swiss chemist Ernst Schultze. Contents 1 Structure 2 Sources 2.1 Dietary Sources 2.2 Biosynthesis 3 Function 3.1 In proteins 3.2 As a precursor 3.3 Treatment of herpes simplex virus 3.4 Possible increases in risk of death from heart disease 3.5 Growth hormone 4 References 5 External links Structure Arginine consists of a 4-carbon aliphatic straight chain, the distal end of which is capped by a complex guanidinium group. With a pKa of 12.48, the guanidinium group is positively charged in neutral, acidic and even most basic environments, and thus imparts basic chemical properties to arginine. Because of the conjugation between the double bond and the nitrogen lone pairs, the positive charge is de-localized, enabling the formation of multiple H-bonds. Sources Dietary Sources Arginine is a nonessential amino acid, meaning it can be manufactured by the human body, and does not need to be obtained directly through the diet. The biosynthetic pathway however does not produce sufficient arginine, and some must still be consumed through diet. Individuals who have poor nutrition or certain physical conditions may be advised to increase their intake of foods containing arginine. Arginine is found in a wide variety of foods, including2: Animal sources: dairy products e.g. cottage cheese, ricotta, milk, yogurt, whey protein drinks, beef, pork e.g. bacon, ham, poultry e.g. chicken and turkey light meat, wild game e.g. pheasant, quail, seafood e.g. halibut, lobster, salmon, shrimp, snails, tuna in water Vegan sources: wheat germ and flour, buckwheat, granola, oatmeal, nuts coconut, pecans, cashews, walnuts, almonds, Brazil nuts, hazel nuts, pine nuts, peanuts, seeds pumpkin, sesame, sunflower, chick peas, cooked soybeans Biosynthesis 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. Citrulline can be derived from multiple sources: from arginine via nitric oxide synthase NOS; from ornithine via catabolism of proline or glutamine/glutamate; from asymmetric dimethylarginine ADMA via DDAH. 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. 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. 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.3 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 proanthocyanidins4 or yohimbine5, has also been used as a treatment for erectile dysfunction. The benefits and functions attributed to oral ingestion of L-arginine include: Precursor for the synthesis of Nitric Oxide NO Stimulation of the release of the most important anti-aging hormone in the body, growth hormone. Improves immune function Reduces healing time of injuries particularly bone Reduces risk of heart disease Increases muscle mass Reduces adipose tissue body fat Helps improve insulin sensitivity Helps decrease blood pressure Alleviates male infertility, improving sperm production and motility Increases circulation throughout the body, including the sex organs 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. 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. Treatment of herpes simplex virus A low ratio of arginine to lysine may be of benefit in the treatment of herpes simplex virus. For more information, refer to Herpes - Treatment. It's also known to sometimes cause hemorrhoidal outbreaks. Possible increases in risk of death from heart disease A clinical trial found that patients taking an L-arginine supplement following a heart attack didn't improve in their vascular tone or their hearts' ability to pump. In fact, more patients died who were taking L-arginine than placebo and the study was stopped early with the recommendation the supplement not be used by heart attack patients. The supplement still is widely marketed.678 Growth hormone Arginine increases the production of growth hormone.9 Reports of its effects on male muscular development are not clearly proven. References ^ 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. ^ L-Arginine Supplements Nitric Oxide Scientific Studies Food Sources. Retrieved on 2007-02-20. ^ Image:Free review.png Enzymes of arginine metabolism J Nutr. 2004 Oct; 13410 Suppl: 2743S-2747S; PMID 15465778 Free text ^ Stanislavov, R. and Nikolova. 2003. Treatment of Erectile Dysfunction with Pycnogenol and L-arginine. Journal of Sex and Marital Therapy, 293: 207 - 213. ^ 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 416: 608-613. ^ Medical College of Georgia. Diabetes Makes It Hard For Blood Vessels To Relax. ScienceDaily 1 February 2008. 1 February 2008 ^ Arginine Therapy in Acute Myocardial Infarction JAMA. 2006 Jan; Vol.295 #1: 58-64; PMID 16391217 Abstract ^ 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. ^ 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. doi:10.1126/science.2237411.br inactive 2008-06-25. PMID 2903866. External links NIST Chemistry Webbook L-Arginine 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 Retrieved from http://en..org/wiki/Arginine Categories: Proteinogenic amino acids | Glucogenic amino acids | Basic amino acids | Essential amino acids | GuanidinesHidden category: Pages with DOIs broken since 2008 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–´ Hrvatski Bahasa Indonesia Italiano עברית LatvieÅ¡u Lëtzebuergesch Lietuvių Nederlands 日本語 پښتو Polski Português РуÑ?Ñ?кий SlovenÄ?ina Suomi Svenska Türkçe УкраїнÑ?ька ä¸æ–‡ This page was last modified on 13 August 2008, at 11:50
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