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Revision as of 13:22, 8 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank').← Previous edit		Latest revision as of 16:28, 16 December 2024 edit undoOrangemike (talk | contribs)Autopatrolled, Administrators126,294 editsm →Commercial use: ce
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	{{chembox		{{chembox
			| Verifiedfields = changed
	| verifiedrevid = 443527288
			| Watchedfields = changed
			| verifiedrevid = 443676645
	| ImageFile = L-Citrullin2.svg		| ImageFile = L-Citrullin2.svg
	| ImageSize = 210px		| ImageSize = 230
			| ImageFile_Ref = {{chemboximage|correct|??}}
	| ImageName = Skeletal formula
	| ImageFile1 = Citrulline-3D-balls.png		| ImageFile1 = L-Citrulline zwitterion ball from xtal.png
	| ImageSize1 = 220px		| ImageSize1 = 230
	| ImageName1 = Ball-and-stick model of zwitterion		| ImageName1 = Ball and stick model of zwitterionic citrulline
			| IUPACName = 2-Amino-5-(carbamoylamino)pentanoic acid<ref>{{cite web|title=Citrulline - Compound Summary|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=833&loc=ec_rcs#x291|work=PubChem Compound|publisher=National Center for Biotechnology Information|access-date=1 May 2012|location=USA|date=16 September 2004|at=Identification}}</ref>
	| IUPACName = 2-Amino-5-(carbamoylamino)pentanoic acid
			|Section1={{Chembox Identifiers
	| OtherNames =
			| CASNo = 627-77-0
	| Section1 = {{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| CASNo_Ref = {{cascite|correct|CAS}}
			| CASNo1 = 13594-51-9
	| ChemSpiderID = 9367
			| CASNo1_Ref = {{cascite|correct|CAS}}
			| CASNo1_Comment = (<small>''D''</small>)
			| CASNo2 = 372-75-8
			| CASNo2_Ref = {{cascite|correct|CAS}}
			| CASNo2_Comment = (<small>''L''</small>)
			| PubChem = 833
			| PubChem1 = 637599
			| PubChem1_Comment = <small>''D''</small>
			| PubChem2 = 9750
			| PubChem2_Comment = <small>''L''</small>
			| ChemSpiderID = 810
			| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
			| ChemSpiderID1 = 553200
			| ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}}
			| ChemSpiderID1_Comment = <small>''D''</small>
			| ChemSpiderID2 = 9367
			| ChemSpiderID2_Ref = {{chemspidercite|changed|chemspider}}
			| ChemSpiderID2_Comment = <small>''L''</small>
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 29VT07BGDA		| UNII = 1OYO2NV4NM
	| KEGG_Ref = {{keggcite|correct|kegg}}		| UNII1_Ref = {{fdacite|correct|FDA}}
			| UNII1 = KNS2VUH6P2
			| UNII1_Comment = (''D'')
			| UNII2_Ref = {{fdacite|correct|FDA}}
			| UNII2 = 29VT07BGDA
			| UNII2_Comment = (''L'')
			| EINECS = 211-012-2
			| DrugBank = DB00155
			| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
	| KEGG = D07706		| KEGG = D07706
			| KEGG_Ref = {{keggcite|correct|kegg}}
	| InChI = 1/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)/t4-/m0/s1
			| MeSHName = Citrulline
	| InChIKey = RHGKLRLOHDJJDR-BYPYZUCNBX
			| ChEBI = 18211
	| ChEMBL_Ref = {{ebicite|correct|EBI}}
			| ChEBI_Ref = {{ebicite|changed|EBI}}
	| ChEMBL = 444814		| ChEMBL = 444814
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| StdInChI = 1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)/t4-/m0/s1
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = RHGKLRLOHDJJDR-BYPYZUCNSA-N
	| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 372-75-8
	| PubChem = 9750
	| IUPHAR_ligand = 722		| IUPHAR_ligand = 722
			| Beilstein = 1725417, 1725415 <small>''D''</small>, 1725416 <small>''L''</small>
	| ChEBI_Ref = {{ebicite|correct|EBI}}
			| Gmelin = 774677 <small>''L''</small>
	| ChEBI = 16349
	| DrugBank = DB00155		| 3DMet = B01217
	| SMILES = O=C(O)(N)CCCNC(=O)N		| SMILES = NC(CCCNC(N)=O)C(O)=O
			| StdInChI = 1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)
			| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChIKey = RHGKLRLOHDJJDR-UHFFFAOYSA-N
			| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
			}}
			|Section2={{Chembox Properties
			| C=6 | H=13 | N=3 | O=3
			| Appearance = White crystals
			| Odor = Odourless
			| LogP = −1.373
			| pKa = 2.508
			| pKb = 11.489
			}}
			|Section3={{Chembox Thermochemistry
			| Entropy = 254.4 J K<sup>−1</sup> mol<sup>−1</sup>
			| HeatCapacity = 232.80 J K<sup>−1</sup> mol<sup>−1</sup>
			}}
			|Section4={{Chembox Related
			| OtherFunction_label = alkanoic acids
			| OtherFunction = {{unbulleted list|]|]|]|]}}
			| OtherCompounds = {{unbulleted list|]|]}}
	}}		}}
	| Section2 = {{Chembox Properties
	| Formula =
	| C=6 | H=13 | N=3 | O=3
	| MolarMass = 175.2 g/mol
	| Appearance =
	| Density =
	| MeltingPt =
	| BoilingPt =
	| Solubility = }}
	| Section3 = {{Chembox Hazards
	| MainHazards =
	| FlashPt =
	| Autoignition = }}
	}}		}}
			The ] '''citrulline''' is an α-].<ref name=":0">{{Citation|last=Banerjee|first=Aryamitra|title=Chapter 15 - Gastrointestinal toxicity biomarkers|date=2014-01-01|url=http://www.sciencedirect.com/science/article/pii/B9780124046306000154|work=Biomarkers in Toxicology|pages=269–277|editor-last=Gupta|editor-first=Ramesh C.|place=Boston|publisher=Academic Press|language=en|doi=10.1016/b978-0-12-404630-6.00015-4|isbn=978-0-12-404630-6|s2cid=88798984 |access-date=2020-11-10}}</ref> Its name is derived from '']'', the ] word for ]. Although named and described by ] since the late 19th century, it was first isolated from watermelon in 1914 by ]ese researchers Yatarō Koga (古賀彌太郎) and Ryō Ōtake (大嶽了)<ref name="Koga1914">{{cite journal
			| last1 = Koga
	The ] '''citrulline''' is an α-]. Its name is derived from ''citrullus'', the ] word for ], from which it was first isolated in 1930.<ref>{{cite journal
	| author = Wada, M		| first1 = Yatarō
			| last2 = Ōtake
	| title = Über Citrullin, eine neue Aminosäure im Presssaft der Wassermelone, Citrullus vulgaris Schrad.
			| first2 = Ryō
	| journal = Biochem. Zeit.
			| title = Study report on the constituents of squeezed watermelon
	| volume = 224
			| journal = Tokyo Kagaku Kaishi
	| issue =
	| pages = 420		| volume = 35
	| year = 1930		| number = 5
	| doi = }}</ref>		| pages = 519–528
			| doi = 10.1246/nikkashi1880.35.519
	It has the idealized ] H<sub>2</sub>NC(O)NH(CH<sub>2</sub>)<sub>3</sub>CH(NH<sub>2</sub>)CO<sub>2</sub>H. It is a key intermediate in the ], the pathway by which mammals excrete ].
			| year = 1914
			}}</ref><ref name="Fragkos2011">{{cite journal
			|last1 = Fragkos
			|first1 = Konstantinos C.
			|last2 = Forbes
			|first2 = Alastair
			| title = Was citrulline first a laxative substance? The truth about modern citrulline and its isolation
			| journal = Nihon Ishigaku Zasshi
			| volume = 57
			| number = 3
			| pages = 275–292
			| url = http://jshm.or.jp/journal/57-3/57-3_275.pdf
			| pmid = 22397107
			| year = 2011
			}}</ref> and further codified by Mitsunori Wada of ] in 1930.<ref name="Wada1930a">{{cite journal
			| last = Wada
			| first = Mitsunori
			| title = On the occurrence of a new amino acid in watermelon. Citrullus vulgaris, Schrad.
			| journal = Proceedings of the Imperial Academy
			| volume = 6
			| number = 1
			| pages = 15–17
			| doi = 10.2183/pjab1912.6.15
			| year = 1930
			}}</ref><ref name="Wada1930b">{{cite journal
			| last = Wada
			| first = Mitsunori
			| title = On the occurrence of a new amino acid in watermelon, Citrullus vulgaris, Schrad.
			| journal = Bulletin of the Agricultural Chemical Society of Japan
			| volume = 6
			| number = 1–5
			| pages = 32–34
			| doi = 10.1271/bbb1924.6.32
			| year = 1930
			}}</ref><ref name="Wada1930c">{{cite journal
			| author = Wada, Mitsunori
			| title = Über Citrullin, eine neue Aminosäure im Preßsaft der Wassermelone, Citrullus vulgaris, Schrad.
			| journal = Biochemische Zeitschrift
			| volume = 224
			| pages = 420–429
			| year = 1930
			| language = de
			}}</ref>
			It has the ] H<sub>2</sub>NC(O)NH(CH<sub>2</sub>)<sub>3</sub>CH(NH<sub>2</sub>)CO<sub>2</sub>H. It is a key intermediate in the ], the pathway by which mammals excrete ] by converting it into urea. Citrulline is also produced as a byproduct of the ] production of ] from the amino acid ], catalyzed by ].<ref>{{cite web|title=Nos2 - Nitric Oxide Synthase|url=https://www.uniprot.org/uniprot/P29477|website=Uniprot.org|publisher=Uniprot Consortium|access-date=10 February 2015}}</ref>
	==Biosynthesis==		==Biosynthesis==
			Citrulline can be derived from:
	Citrulline is made from ] and ] in one of the central reactions in the urea cycle. It is also produced from ] as a by-product of the reaction catalyzed by ] family (NOS; EC 1.14.13.39).<ref>{{cite book |author=Cox M, Lehninger AL, Nelson DR |title=Lehninger principles of biochemistry |publisher=Worth Publishers |location=New York |year=2000 |pages= |isbn=1-57259-153-6 |edition=3rd |doi= |accessdate=}}</ref> Arginine is first oxidized into N-hydroxyl-arginine, which is then further oxidized to citrulline concomitant with release of nitric oxide.
			* from arginine via ], as a byproduct of the production of nitric oxide for ] purposes
			* from ] through the breakdown of ] or ]/]
			* from ] via DDAH
			Citrulline is made from ] and ] in one of the central reactions in the urea cycle. It is also produced from ] as a byproduct of the reaction catalyzed by ] family (NOS; ).<ref>{{cite book |vauthors=Cox M, Lehninger AL, Nelson DR |title=Lehninger principles of biochemistry |publisher=Worth Publishers |location=New York |year=2000 |page= |isbn=978-1-57259-153-0 |edition=3rd |access-date= 13 March 2020 |url=https://archive.org/details/lehningerprincip01lehn }}</ref> It is also prevalent in ] at the inner root ] and medulla of hair follicles, where it is synthesized from arginine.<ref>{{Cite journal
			| last1 = Rogers | first1 = G. E.
			| last2 = Rothnagel | first2 = J. A.
			| title = A sensitive assay for the enzyme activity in hair follicles and epidermis that catalyses the peptidyl-arginine-citrulline post-translational modification
			| journal = Current Problems in Dermatology
			| volume = 11
			| pages = 171–184
			| year = 1983
			| pmid = 6653155
			| doi = 10.1159/000408673
			| isbn = 978-3-8055-3752-0
			}}</ref> ] is first oxidized into ''N''-hydroxyl-arginine, which is then further oxidized to citrulline concomitant with release of nitric oxide.
			Citrulline is also made by ] of the small intestine.<ref name=":0" /><ref>{{Citation|last=DeLegge|first=Mark H.|title=Chapter 7 - Enteral Access and Enteral Nutrition in Patients With Short Bowel Syndrome|date=2019-01-01|url=http://www.sciencedirect.com/science/article/pii/B978012814330800007X|work=Adult Short Bowel Syndrome|pages=81–96|editor-last=Corrigan|editor-first=Mandy L.|publisher=Academic Press|language=en|doi=10.1016/b978-0-12-814330-8.00007-x|isbn=978-0-12-814330-8|s2cid=81295089|access-date=2020-11-10|editor2-last=Roberts|editor2-first=Kristen|editor3-last=Steiger|editor3-first=Ezra}}</ref>
	==Function==		==Function==
			Citrulline is a metabolic intermediate within the ], which is the pathway by which mammals excrete ammonia by converting it into urea. Citrulline is also produced as a byproduct of the enzymatic production of nitric oxide from the amino acid arginine, catalyzed by nitric oxide synthase. In the yeast species Saccharomyces cerevisiae, citrulline is a metabolic intermediate in the latter, cytosolic half of the arginine biosynthesis pathway.<ref>{{cite web | url=https://pathway.yeastgenome.org/YEAST/new-image?object=CITRUL-BIO2-PWY | title=Saccharomyces cerevisiae citrulline biosynthesis }}</ref>
	Although citrulline is not coded for by ] directly, several proteins are known to contain citrulline as a result of a ]. These citrulline residues are generated by a family of enzymes called peptidylarginine deiminases (PADs), which convert arginine into citrulline in a process called ] or deimination. Proteins that normally contain citrulline residues include ] (MBP), ], and several ] proteins, whereas other proteins, such as ] and ] are susceptible to citrullination during cell death and tissue ].
			Several proteins contain citrulline as a result of a ]. These citrulline residues are generated by a family of enzymes called ]s (PADs), which convert arginine into citrulline in a process called ] or deimination with the help of calcium ions. Proteins that normally contain citrulline residues include ] (MBP), ], and several ] proteins, whereas other proteins, such as ] and ] are susceptible to citrullination during cell death and tissue ].
	Patients with ] often have detectable antibodies against proteins containing citrulline. Although the origin of this immune response is not known, detection of antibodies reactive with citrulline (]) containing proteins or peptides is now becoming an important help in the ].<ref>{{cite journal |author=Coenen D, Verschueren P, Westhovens R, Bossuyt X |title=Technical and diagnostic performance of 6 assays for the measurement of citrullinated protein/peptide antibodies in the diagnosis of rheumatoid arthritis |journal=Clin. Chem. |volume=53 |issue=3 |pages=498–504 |year=2007 |month=March |pmid=17259232 |doi=10.1373/clinchem.2006.078063 |url=http://www.clinchem.org/cgi/content/full/53/3/498}}</ref>
			Circulating citrulline concentration is a ] of intestinal functionality.<ref>{{Cite journal|last1=Fragkos|first1=Konstantinos C.|last2=Forbes|first2=Alastair|date=2017-10-12|title=Citrulline as a marker of intestinal function and absorption in clinical settings: A systematic review and meta-analysis|journal=United European Gastroenterology Journal|volume=6|issue=2|pages=181–191|language=en|doi=10.1177/2050640617737632|pmid=29511548|pmc=5833233}}</ref><ref>{{cite journal | last1 = Crenn | first1 = P. | display-authors = etal | year = 2000 | title = Post-absorptive plasma citrulline concentration is a marker of intestinal failure in short bowel syndrome patients | journal = Gastroenterology | volume = 119 | issue = 6| pages = 1496–505 | doi=10.1053/gast.2000.20227| pmid = 11113071 | doi-access = free }}</ref>
	In recent studies, citrulline has been found to relax blood vessels.<ref></ref>
	==Sources==		==Commercial use==
			L-citrulline is sold as a ], usually in powder form. Advocates suggest that since L-citrulline boosts nitric oxide production, helping arterial function and thus blood flow throughout the body, this might be helpful in treating or preventing various ailments.
	Citrulline in the form of citrulline ] is sold as a performance-enhancing athletic ], which was shown to reduce muscle fatigue in a preliminary clinical trial.<ref>{{cite journal |author=Bendahan D, Mattei JP, Ghattas B, Confort-Gouny S, Le Guern ME, Cozzone PJ |title=Citrulline/malate promotes aerobic energy production in human exercising muscle |journal=Br J Sports Med |volume=36 |issue=4 |pages=282–9 |year=2002 |month=Aug |pmid=12145119 |pmc=1724533 |url=http://bjsm.bmj.com/cgi/pmidlookup?view=long&pmid=12145119 |doi=10.1136/bjsm.36.4.282}}</ref>
			*Lowering ] in people with elevated blood pressure.
			*Easing symptoms of mild-to-moderate ], with fewer risks than ].
			*Ameliorating circulatory problems such as slow wound healing due to ].
			*Raising muscle protein levels, preventing malnourishment in the elderly and possibly improving athletic performance.
			*Treating intestinal problems, including ], ] and radiation-caused ] damage
			*Various genetic disorders and health conditions such as liver disease, ] and certain ]s.
			These assertions are based on animal studies, and like most dietary supplement claims have not be endorsed by the ].<ref>{{cite web |last1=Miller |first1=Kelli |title=L-citrulline |url=https://www.webmd.com/vitamins-and-supplements/l-citrulline-uses-and-risks |website=WebMD |publisher=WebMD LLC |access-date=16 December 2024}}</ref>
	The rind of ] (''Citrullus lanatus'') is a good natural source of citrulline.<ref></ref>
			L-citrulline is added to certain ]s such as ] and touted for its ] effects.<ref>Label on Reign Inferno Watermelon Overlord can; Reign Beverage Company: Los Angeles, 2020</ref>
	==See also==		==See also==
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	==References==		==References==
	{{reflist}}		{{reflist|20em}}
			{{Non-proteinogenic amino acids}}
	]
			{{Amino acid metabolism intermediates}}
			]
	]		]
	]		]
			]
			]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]