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14-September-2008 18:38:45 - Citrulline Chemical structure of Citrulline Citrulline Systematic IUPAC name 2-amino-5-carbamoylaminopentanoic acid Identifiers CAS number 372-75-8 PubChem 9750 Chemical data Formula C6H13N3O3 Molar mass 175.2 Complete data The organic compound citrulline is an α-amino acid. Its name is derived from citrullus, the Latin word for watermelon, from which it was first isolated in 1930.1 It has the idealized formula H2NCONHCH23CHNH2CO2H. It is a key intermediate in the urea cycle, the pathway by which mammals excrete ammonia. Contents 1 Biosynthesis 2 Function 3 Sources 4 See also 5 References Biosynthesis Citrulline is made from ornithine and carbamoyl phosphate in one of the central reactions in the urea cycle. It is also produced from arginine as a by-product of the reaction catalyzed by NOS family NOS; EC 1.14.13.39.2 Arginine is first oxidized into N-hydroxyl-arginine, which is then further oxidized to citrulline concomitant with release of nitric oxide. Function Although citrulline is not coded for by DNA directly, several proteins are known to contain citrulline as a result of a posttranslational modification. These citrulline residues are generated by a family of enzymes called peptidylarginine deiminases PADs, which convert arginine into citrulline in a process called citrullination or deimination. Proteins that normally contain citrulline residues include myelin basic protein MBP, filaggrin, and several histone proteins, whereas other proteins, such as fibrin and vimentin are susceptible to citrullination during cell death and tissue inflammation. Patients with rheumatoid arthritis often have detectable antibodies against proteins containing citrulline. Although the origin of this immune response is not known, detection of antibodies reactive with citrulline anti-citrullinated protein antibodies containing proteins or peptides is now becoming an important help in the diagnosis of rheumatoid arthritis.3 In recent studies, citrulline has been found to relax blood vessels.4 Sources Citrulline in the form of citrulline malate is sold as a performance-enhancing athletic dietary supplement which is said to reduce muscle fatigue.5 The rind of watermelon Citrullus lanatus is a good natural source of citrulline.6 See also Citrullinemia References ^ Wada, M 1930. Ãœber Citrullin, eine neue Aminosäure im Presssaft der Wassermelone, Citrullus vulgaris Schrad.. Biochem. Zeit. 224: 420. ^ Nelson, D. L.; Cox, M. M. Lehninger, Principles of Biochemistry 3rd Ed. Worth Publishing: New York, 2000. ISBN 1-57259-153-6. ^ Coenen D, Verschueren P, Westhovens R, Bossuyt X March 2007. Technical and diagnostic performance of 6 assays for the measurement of citrullinated protein/peptide antibodies in the diagnosis of rheumatoid arthritis. Clin. Chem. 53 3: 498-504. doi:10.1373/clinchem.2006.078063. PMID 17259232. ^ Viagra-Like Effects From Watermelon ^ Citrulline/malate promotes aerobic energy producti...Br J Sports Med. 2002 - PubMed Result ^ Watermelon May Have Viagra-effect Retrieved from http://en..org/wiki/Citrulline Categories: Amino acids | Ureas 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 Deutsch Español Français Italiano 日本語 Polski Português РуÑ?Ñ?кий Svenska УкраїнÑ?ька ä¸æ–‡ This page was last modified on 21 August 2008, at 03:05
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