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an amino acid that does not occur in proteins but is an intermediate in the conversion of ornithine to arginine

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/11/03 09:59:21」(JST)

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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 1914 by Koga & Odake. It was finally identified by Wada in 1930.^[2] It has the formula H₂NC(O)NH(CH₂)₃CH(NH₂)CO₂H. It is a key intermediate in the urea cycle, the pathway by which mammals excrete ammonia.

Biosynthesis[edit]

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).^[3] It is made from arginine by the enzyme trichohyalin at the inner root sheath and medulla of hair follicles.^[4] Arginine is first oxidized into N-hydroxyl-arginine, which is then further oxidized to citrulline concomitant with release of nitric oxide.

Function[edit]

Several proteins 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.^[5]

Circulating citrulline concentration is, in humans, a biomarker of intestinal functionality.^[6]

Sources[edit]

Citrulline in the form of citrulline malate is sold as a performance-enhancing athletic dietary supplement, which was shown to reduce muscle fatigue in a preliminary clinical trial.^[7]

The rind of watermelon (Citrullus lanatus) is a good natural source of citrulline.^[8]

References[edit]

^ "Citrulline - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification. Retrieved 1 May 2012.
^ Fearon, William Robert (1939). "The Carbamido Diacetyl Reaction: A Test For Citrulline". Biochemical Journal 33 (6): 902–907.
^ Cox M, Lehninger AL, Nelson DR (2000). Lehninger principles of biochemistry (3rd ed.). New York: Worth Publishers. ISBN 1-57259-153-6.
^ Rogers, G. E.; Rothnagel, J. A. (1983). "A sensitive assay for the enzyme activity in hair follicles and epidermis that catalyses the peptidyl-arginine-citrulline post-translational modification". Current problems in dermatology 11: 171–184. PMID 6653155. edit
^ 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.
^ Crenn P. et al. Post-absorptive plasma citrulline concentration is a marker of intestinal failure in short bowel syndrome patients. Gastroenterology 119 (2000) , 1496-505
^ Bendahan D, Mattei JP, Ghattas B, Confort-Gouny S, Le Guern ME, Cozzone PJ (Aug 2002). "Citrulline/malate promotes aerobic energy production in human exercising muscle". Br J Sports Med 36 (4): 282–9. doi:10.1136/bjsm.36.4.282. PMC 1724533. PMID 12145119.
^ Watermelon May Have Viagra-effect

UpToDate Contents

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1. 尿素サイクル障害：管理 urea cycle disorders management
2. 成人における短腸症候群のマネージメント management of the short bowel syndrome in adults
3. 臨床的に有用な生物学的マーカーによる関節リウマチの診断および転帰評価 clinically useful biologic markers in the diagnosis and assessment of outcome in rheumatoid arthritis
4. 尿素サイクル障害：臨床的特徴および診断 urea cycle disorders clinical features and diagnosis
5. 短腸症候群の病態生理 pathophysiology of the short bowel syndrome

English Journal

Lessons to be learned from periodontitis.

Janssen KM, Vissink A, de Smit MJ, Westra J, Brouwer E.SourceaDepartment of Oral and Maxillofacial Surgery bCenter for Dentistry and Oral Hygiene cDepartment of Rheumatology and Clinical Immunology, University Medical Center Groningen, University of Groningen, Groningen, The Netherlands.
Current opinion in rheumatology.Curr Opin Rheumatol.2013 Mar;25(2):241-7. doi: 10.1097/BOR.0b013e32835d833d.
PURPOSE OF REVIEW: This article reviews the link between periodontitis and rheumatoid arthritis (RA) with regard to similarities in genetic risk factors and immunopathogenesis. Emphasis is paid to the potential role of the periodontal pathogen Porphyromonas gingivalis in the etiopathogenesis of both
PMID 23370377

Citrulline: From metabolism to therapeutic use.

Bahri S, Zerrouk N, Aussel C, Moinard C, Crenn P, Curis E, Chaumeil JC, Cynober L, Sfar S.SourceLaboratoire de Pharmacie Galénique, Faculté de Pharmacie de Monastir, Monastir, Tunisia; Laboratoire de Pharmacie Galénique-Faculté de Pharmacie Université Paris Descartes, Paris, France. Electronic address: senda.bahri@rns.tn.
Nutrition (Burbank, Los Angeles County, Calif.).Nutrition.2013 Mar;29(3):479-84. doi: 10.1016/j.nut.2012.07.002. Epub 2012 Sep 28.
Citrulline possesses a highly specific metabolism that bypasses splanchnic extraction because it is not used by the intestine or taken up by the liver. The administration of citrulline may be used to deliver available nitrogen for protein homeostasis in peripheral tissues and as an arginine precurso
PMID 23022123

Japanese Journal

High Citrulline-to-Arginine Ratio Associated With Blood Pressure Abnormalities in Children With Early Chronic Kidney Disease

Lin Ying-Jui,Hsu Chien-Ning,Lo Mao-Hung,Huang Chien-Fu,Chien Shao-Ju,Tain You-Lin
Circulation Journal 77(1), 181-187, 2013
… NO synthase can metabolize L-arginine (ARG) to generate NO and L-citrulline (CIT). …
NAID 130001870110

長期HPN管理短腸症候群の1例 : 成人小腸移植適応患者の現状

橋詰直樹,飯沼泰史,新田幸壽,内藤真一,平山裕,飯田久貴,山田徹
日本小児外科学会雑誌 48(4), 743-748, 2012-06-20
… 幽門輪から回盲弁まで約4cmであった.術後より中心静脈管理を行い,生後4か月時よりHPNを開始した.22歳となった現在もHPNをほぼ24時間かけて持続投与している.現時点の残存小腸は幽門輪から約30cmであり,血中Citrulline値は5.9nmol/mlと低値であった.カテーテルはこれまでに感染・閉塞・事故抜去などで計21回のカテーテル交換を行なっている.左右内頸静脈は開存しているが,左右鎖骨下静脈は閉塞し挿入不可能である.現時点で …
NAID 110009470929

Related Pictures

★リンクテーブル★

リンク元	「オルニチン回路」「シトルリン」

「オルニチン回路」

Citrulline
	IUPAC name 2-Amino-5-(carbamoylamino)pentanoic acid
Identifiers
CAS number	627-77-0 , 13594-51-9 R , 372-75-8 S
PubChem	833, 637599 R, 9750 S
ChemSpider	810 , 553200 R , 9367 S
UNII	29VT07BGDA
EC number	211-012-2
DrugBank	DB00155
KEGG	D07706
MeSH	Citrulline
ChEBI	CHEBI:18211
ChEMBL	CHEMBL444814
IUPHAR ligand	722
Beilstein Reference	1725417, 1725415 R, 1725416 S
Gmelin Reference	774677 S
3DMet	B01217
Jmol-3D images	Image 1; Image 2
	SMILES NC(CCC[nH]:c(:[nH2]):[o])c(:[o]):[oH] NC(CCCNC(N)=O)C(O)=O ;
	InChI InChI=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) ; Key: RHGKLRLOHDJJDR-UHFFFAOYSA-N ;
Properties
Molecular formula	C6H13N3O3
Molar mass	175.19 g mol−1
Appearance	White crystals
Odor	Odourless
log P	−1.373
Acidity (pKa)	2.508
Basicity (pKb)	11.489
Thermochemistry
Standard molar; entropy So298	254.4 J K−1 mol−1
Specific heat capacity, C	232.80 J K−1 mol−1
Related compounds
Related alkanoic acids	N-Acetylaspartic acid; Aceglutamide; N-Acetylglutamic acid; Pivagabine;
Related compounds	Bromisoval; Carbromal;
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

　　[★]

英: ornithine cycle
同: 尿素サイクル尿素回路 urea cycle、クレブス-ヘンゼライト回路 Krebs-Henseleit cycle、オルニチンサイクル
関: オルニチン、尿素

オルニチン回路に含まれる分子はアミノ酸である：アミノ基とカルボン酸を両方持つもの
最終産物である尿素の窒素は、アンモニアとアスパラギン酸に由来する

ミトコンドリア内の反応

1) アンモニア + 炭酸 + 2ATP → ADP + Pi + カルバモイルリン酸 
　　　　　　　　　　　　5)から
　　　　　　　　　　　　↓
2) カルバモイルリン酸 + オルニチン → シトルリン + Pi 
　　　　　　　　　　　　　　　　　　　↓
　　　　　　　　　　　　　　　　　　　3)へ

サイトソルの反応

　　2)から
　　↓
3) シトルリン + アスパラギン酸 + ATP → AMP + ピロリン酸 + アルギニノコハク酸 
4) アルギニノコハク酸 → フマル酸 + アルギニン 
5) アルギニン + 水 → 尿素 + オルニチン 
　　　　　　　　　　　　　　　↓
　　　　　　　　　　　　　　　2)へ

|
ornithine
|
----------mitochondria
|
ornithine
|
|<-carbamoyl phosphate {ornithine transcarbamoylase}
|
citrulline
|
----------mitochondria
|
citrulline
|
|<-aspartate {argininosuccinate synthase}
|
argininosuccinate
| 
|->fumarate {argininosuccinase}
|
arginine
|
|<-H2O
|           {arginase}
|->urea
|
ornithine
|

臨床関連

尿素サイクル異常症

「シトルリン」

　　[★]

英: citrulline
関

アルギニン残基がペプチジルある銀・デイミナーゼによって変換されたアミノ酸。

[1] "Citrulline - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification. Retrieved 1 May 2012.

[2] Fearon, William Robert (1939). "The Carbamido Diacetyl Reaction: A Test For Citrulline". Biochemical Journal 33 (6): 902–907.

[3] Cox M, Lehninger AL, Nelson DR (2000). Lehninger principles of biochemistry (3rd ed.). New York: Worth Publishers. ISBN 1-57259-153-6.

[4] Rogers, G. E.; Rothnagel, J. A. (1983). "A sensitive assay for the enzyme activity in hair follicles and epidermis that catalyses the peptidyl-arginine-citrulline post-translational modification". Current problems in dermatology 11: 171–184. PMID 6653155. edit

[5] 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.

[6] Crenn P. et al. Post-absorptive plasma citrulline concentration is a marker of intestinal failure in short bowel syndrome patients. Gastroenterology 119 (2000) , 1496-505

[7] Bendahan D, Mattei JP, Ghattas B, Confort-Gouny S, Le Guern ME, Cozzone PJ (Aug 2002). "Citrulline/malate promotes aerobic energy production in human exercising muscle". Br J Sports Med 36 (4): 282–9. doi:10.1136/bjsm.36.4.282. PMC 1724533. PMID 12145119.

[8] Watermelon May Have Viagra-effect

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案内

citrulline