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Record Information
Version	2.0
Creation Date	2012-05-31 13:01:55 -0600
Update Date	2015-09-13 12:56:09 -0600
Secondary Accession Numbers	ECMDB00904
Identification
Name:	Citrulline
Description	Citrulline is an amino acid 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). In this reaction arginine is first oxidized into N-hydroxyl-arginine, which is then further oxidized to citrulline concomitant with the release of nitric oxide.; EC 1.14.13.39). Citrulline's name is derived from citrullus, the Latin word for watermelon, from which it was first isolated.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xb0dfae5c> Close
Synonyms:	α-amino-γ-ureidovalerate α-amino-γ-ureidovaleric acid γureidonorvaline (2S)-2-amino-5-(carbamoylamino)pentanoate (2S)-2-amino-5-(carbamoylamino)pentanoic acid (S)-2-amino-5-(aminocarbonyl)aminopentanoate (S)-2-amino-5-(aminocarbonyl)aminopentanoic acid (S)-2-Amino-5-ureidopentanoate (S)-2-Amino-5-ureidopentanoic acid 2-Amino-5-uredovalerate 2-Amino-5-uredovaleric acid 2-Amino-5-ureidovalerate 2-Amino-5-ureidovaleric acid A-Amino-D-ureidovalerate A-Amino-D-ureidovaleric acid a-amino-delta-Ureidovalerate a-amino-delta-Ureidovaleric acid a-amino-g-Ureidovalerate a-amino-g-Ureidovaleric acid a-amino-δ-Ureidovalerate a-amino-δ-Ureidovaleric acid Alpha-Amino-delta-ureidovalerate Alpha-Amino-delta-ureidovaleric acid Alpha-Amino-gamma-ureidovalerate Alpha-Amino-gamma-ureidovaleric acid Amino-ureidovalerate Amino-ureidovaleric acid CIR CIT Citrulline Cytrulline D-Ureidonorvaline Delta-Ureidonorvaline DL-citrulline Gammaureidonorvaline H-Cit-oh L(+)-2-Amino-5-ureidovalerate L(+)-2-Amino-5-ureidovaleric acid L(+)-Citrulline L-2-Amino-5-ureido-valerate L-2-Amino-5-ureido-valeric acid L-2-Amino-5-ureidovalerate L-2-Amino-5-ureidovaleric acid L-Citrulline L-Cytrulline L-N5-carbamoyl-Ornithine Nγ-carbamylornithine N()-Carbamylornithine N(5)-(Aminocarbonyl)-DL-Ornithine N(delta)-Carbamylornithine N(δ)-Carbamylornithine N-Carbamylornithine N5-(Aminocarbonyl)-L-ornithine N5-(aminocarbonyl)-Ornithine N5-(Aminocarbonyl)ornithine N5-Carbamoyl-L-ornithine N5-carbamoylornithine N5-carbamylornithine Nγ-carbamylornithine N5-(Aminocarbonyl)-L-ornithine N5-(aminocarbonyl)ornithine ND-carbamylornithine Ndelta-carbamy-ornithine Ndelta-carbamylornithine Ngamma-carbamylornithine Sitrulline Ureidonorvaline Ureidovalerate Ureidovaleric acid α-amino-γ-Ureidovalerate α-amino-γ-Ureidovaleric acid α-amino-δ-Ureidovalerate α-amino-δ-Ureidovaleric acid δ-Ureidonorvaline
Chemical Formula:	C6H13N3O3
Weight:	Average: 175.1857 Monoisotopic: 175.095691297
InChI Key:	RHGKLRLOHDJJDR-BYPYZUCNSA-N
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)/t4-/m0/s1
CAS number:	372-75-8
IUPAC Name:	(2S)-2-amino-5-(carbamoylamino)pentanoic acid
Traditional IUPAC Name:	L-citrulline
SMILES:	N[C@@H](CCCNC(N)=O)C(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Sub Class	Amino acids, peptides, and analogues
Direct Parent	L-alpha-amino acids
Alternative Parents	Fatty acids and conjugates Isoureas Amino acids Monocarboxylic acids and derivatives Carboxylic acids Carboximidamides Organopnictogen compounds Organic oxides Monoalkylamines Imines Hydrocarbon derivatives Carbonyl compounds
Substituents	L-alpha-amino acid Fatty acid Isourea Amino acid Carboximidic acid derivative Carboxylic acid Monocarboxylic acid or derivatives Carboximidamide Amine Hydrocarbon derivative Primary amine Organooxygen compound Organonitrogen compound Organic oxide Primary aliphatic amine Organopnictogen compound Imine Organic oxygen compound Organic nitrogen compound Carbonyl group Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	citrulline (CHEBI:16349 ) Other amino acids (C00327 )
Physical Properties
State:	Solid
Charge:	0
Melting point:	235.5 °C
Experimental Properties:	Property Value Source Water Solubility: 212 mg/mL [HMP experimental] PhysProp LogP: -3.19 [SANGSTER (1994)] PhysProp
Predicted Properties	Property Value Source Water Solubility 21.8 g/L ALOGPS logP -3.3 ALOGPS logP -3.9 ChemAxon logS -0.9 ALOGPS pKa (Strongest Acidic) 2.27 ChemAxon pKa (Strongest Basic) 9.23 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 118.44 Ų ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 41.33 m³·mol⁻¹ ChemAxon Polarizability 17.35 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	Carbamoylphosphate + Ornithine + L-Ornithine <> Citrulline + Hydrogen ion + Phosphate L-Aspartic acid + Adenosine triphosphate + Citrulline <> Adenosine monophosphate + Argininosuccinic acid + Hydrogen ion + Pyrophosphate Carbamoylphosphate + Ornithine <> Phosphate + Citrulline Adenosine triphosphate + Citrulline + L-Aspartic acid <> Adenosine monophosphate + Pyrophosphate + Argininosuccinic acid N-Acetyl-L-citrulline + Water <> Acetic acid + Citrulline L-Aspartic acid + Citrulline + Adenosine triphosphate > Hydrogen ion + L-arginino-succinate + Pyrophosphate + Adenosine monophosphate Ornithine + Carbamoylphosphate <> Hydrogen ion + Citrulline + Phosphate Adenosine triphosphate + Citrulline + L-Aspartic acid > Adenosine monophosphate + Pyrophosphate + 2-(N(omega)-L-arginino)succinate Carbamoylphosphate + Ornithine > Inorganic phosphate + Citrulline Adenosine triphosphate + Citrulline + L-Aspartic acid + L-Aspartic acid > Pyrophosphate + Adenosine monophosphate + Argininosuccinic acid Ornithine + Carbamoylphosphate + Ornithine > Phosphate + Hydrogen ion + Citrulline L-Aspartic acid + Adenosine triphosphate + Citrulline <> Adenosine monophosphate + Argininosuccinic acid + Hydrogen ion + Pyrophosphate Carbamoylphosphate + Ornithine + L-Ornithine <> Citrulline + Hydrogen ion + Phosphate L-Aspartic acid + Adenosine triphosphate + Citrulline <> Adenosine monophosphate + Argininosuccinic acid + Hydrogen ion + Pyrophosphate
SMPDB Pathways:	Aspartate metabolism PW000787 arginine metabolism PW000790
KEGG Pathways:	Alanine, aspartate and glutamate metabolism ec00250 Arginine and proline metabolism ec00330 Metabolic pathways eco01100
EcoCyc Pathways:	arginine biosynthesis I ARGSYN-PWY
Concentrations
	Concentration Strain Media Growth Status Growth System Temperature Details 1350± 0 uM K12 NCM3722 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose Mid-Log Phase Shake flask and filter culture 37 oC PMID: 19561621 931± 0 uM K12 NCM3722 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerol Mid-Log Phase Shake flask and filter culture 37 oC PMID: 19561621 516± 0 uM K12 NCM3722 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetate Mid-Log Phase Shake flask and filter culture 37 oC PMID: 19561621 38± 0 uM BW25113 48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco Stationary Phase, glucose limited Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h 37 oC PMID: 17379776 270± 14 uM BL21 DE3 Luria-Bertani (LB) media Stationary phase cultures (overnight culture) Shake flask 37 oC Experimentally Determined Download Details Find out more about how we convert literature concentrations.
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) splash10-0a4i-0920000000-2d92b63cd5d9648023b8 View in MoNA GC-MS GC-MS Spectrum - GC-MS (3 TMS) splash10-00di-9610000000-2e7cd23afc2adcef35a3 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-0a4i-0920000000-2d92b63cd5d9648023b8 View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-00di-9610000000-2e7cd23afc2adcef35a3 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-007o-9100000000-1f8dd2c6648b104639c7 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive splash10-00dl-9410000000-37909012a777213f8566 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) splash10-0a4i-0900000000-4c1d7af748a47e489949 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) splash10-00di-9000000000-988fced362fc0da157c9 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) splash10-00di-9000000000-0818e0e8bcee12692498 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-004j-0900000000-5fa8a338dcd2f2a6bdd2 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-004i-0900000000-16763200aa07f7629ad4 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-03di-3900000000-d9cfc5187aa799f6f978 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-0a4i-0900000000-10ee9a593e13550bec1c View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-004i-0900000000-45d272576af34c9512a3 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-014i-3900000000-6177a284fdea5a3f1306 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-0a4i-0900000000-d9456d45e2dbd7a3df10 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive splash10-004i-0900000000-ada57cdc73bda93be483 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative splash10-008a-0904000000-23fbe48f82e515087d68 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative splash10-03di-5900000000-78afcbaf8b8b3eabf174 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative splash10-001i-0900000000-8fb191d4c20fd54b9282 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative splash10-00di-0900000000-da484f0362a8dca5127e View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative splash10-00e9-0900000000-46229b4f77feabb3f857 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative splash10-001i-0900000000-4aca1022c393602a297d View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative splash10-001i-0900000000-3bc2eff2e907b7734cc8 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative splash10-001i-3900000000-2613bf40e3be814da86f View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative splash10-0006-9300000000-e83287bbc060eb9cf6f3 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive splash10-056r-0900000000-694a8872bdfd7eec1f2b View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive splash10-08fr-2900000000-15b4711991ea9985fb2b View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive splash10-00di-9300000000-915fbb73e0b728420e4a View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive splash10-00di-9000000000-67e60567f5c062728350 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive splash10-00di-9000000000-25140713431edd7c5eea View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,1H] 2D NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View in JSpectraViewer
References
References:	Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621 Booth FA, Haworth JC, Dilling LA, Perry TL, Greenberg CR, Seargeant LE, Penn AM, Rhead WJ: Mitochondrial encephalomyopathy with associated aminoacidopathy in a male sibship. J Pediatr. 1989 Jul;115(1):81-8. Pubmed: 2738799 Crenn P, Coudray-Lucas C, Thuillier F, Cynober L, Messing B: Postabsorptive plasma citrulline concentration is a marker of absorptive enterocyte mass and intestinal failure in humans. Gastroenterology. 2000 Dec;119(6):1496-505. Pubmed: 11113071 Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. Pubmed: 12297216 DeLong GR, Glick TH: Ammonia metabolism in Reye syndrome and the effect of citrulline. Ann Neurol. 1982 Jan;11(1):53-8. Pubmed: 7059128 Engelborghs S, Marescau B, De Deyn PP: Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Neurochem Res. 2003 Aug;28(8):1145-50. Pubmed: 12834252 Facchinetti F, Longo M, Piccinini F, Neri I, Volpe A: L-arginine infusion reduces blood pressure in preeclamptic women through nitric oxide release. J Soc Gynecol Investig. 1999 Jul-Aug;6(4):202-7. Pubmed: 10486782 Fleisher LD, Harris CJ, Mitchell DA, Nadler HL: Citrullinemia: prenatal diagnosis of an affected fetus. Am J Hum Genet. 1983 Jan;35(1):85-90. Pubmed: 6823975 Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7. Pubmed: 6198473 Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776 Jianfeng G, Weiming Z, Ning L, Fangnan L, Li T, Nan L, Jieshou L: Serum citrulline is a simple quantitative marker for small intestinal enterocytes mass and absorption function in short bowel patients. J Surg Res. 2005 Aug;127(2):177-82. Pubmed: 15921697 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882 Le Boucher J, Charret C, Coudray-Lucas C, Giboudeau J, Cynober L: Amino acid determination in biological fluids by automated ion-exchange chromatography: performance of Hitachi L-8500A. Clin Chem. 1997 Aug;43(8 Pt 1):1421-8. Pubmed: 9267323 Liappis N, Pohl B, Weber HP, el-Karkani H: [Free amino acids in the saliva of children with phenylketonuria] Klin Padiatr. 1986 Jan-Feb;198(1):25-8. Pubmed: 3959486 Maruyama H, Ogawa M, Nishio T, Kobayashi K, Saheki T, Sunohara N: Citrullinemia type II in a 64-year-old man with fluctuating serum citrulline levels. J Neurol Sci. 2001 Jan 1;182(2):167-70. Pubmed: 11137523 McLaurin J, Moscarello MA: The preparation of antibodies reactive against citrulline-containing charge isomers of myelin basic protein but not against the arginine-containing charge isomers. Anal Biochem. 1990 Dec;191(2):272-7. Pubmed: 1707596 Melis GC, Boelens PG, van der Sijp JR, Popovici T, De Bandt JP, Cynober L, van Leeuwen PA: The feeding route (enteral or parenteral) affects the plasma response of the dipetide Ala-Gln and the amino acids glutamine, citrulline and arginine, with the administration of Ala-Gln in preoperative patients. Br J Nutr. 2005 Jul;94(1):19-26. Pubmed: 16115328 Origuchi Y, Ushijima T, Sakaguchi M, Akaboshi I, Matsuda I: Citrullinemia presenting as uncontrollable epilepsy. Brain Dev. 1984;6(3):328-31. Pubmed: 6486381 Potter MA, Zeesman S, Brennan B, Kobayashi K, Gao HZ, Tabata A, Saheki T, Whelan DT: Pregnancy in a healthy woman with untreated citrullinemia. Am J Med Genet A. 2004 Aug 15;129(1):77-82. Pubmed: 15266621 Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. Pubmed: 14992292 Reparon-Schuijt CC, van Esch WJ, van Kooten C, Schellekens GA, de Jong BA, van Venrooij WJ, Breedveld FC, Verweij CL: Secretion of anti-citrulline-containing peptide antibody by B lymphocytes in rheumatoid arthritis. Arthritis Rheum. 2001 Jan;44(1):41-7. Pubmed: 11212174 Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195 Wheatley DN, Kilfeather R, Stitt A, Campbell E: Integrity and stability of the citrulline-arginine pathway in normal and tumour cell lines. Cancer Lett. 2005 Sep 28;227(2):141-52. Pubmed: 16112417 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:	Kakimoto, Toshio; Shibatani, Takeji; Nishimura, Noriyuki; Chibata, Ichiro. Enzymic production of L-citrulline by Pseudomonas putida. Applied Microbiology (1971), 22(6), 992-9.
Material Safety Data Sheet (MSDS)	Download (PDF)
Links
External Links:	Resource Link CHEBI ID 18211 HMDB ID HMDB00904 Pubchem Compound ID 9750 Kegg ID C00327 ChemSpider ID 9367 Wikipedia Citrulline BioCyc ID L-CITRULLINE EcoCyc ID L-CITRULLINE Ligand Expo CIR

Enzymes