2.02012-05-31 13:01:55 -06002015-09-13 12:56:09 -0600ECMDB00904M2MDB000198CitrullineCitrulline 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. α-amino-γ-ureidovalerateα-amino-γ-ureidovaleric acidγureidonorvaline(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 acid2-Amino-5-uredovalerate2-Amino-5-uredovaleric acid2-Amino-5-ureidovalerate2-Amino-5-ureidovaleric acidA-Amino-D-ureidovalerateA-Amino-D-ureidovaleric acida-amino-delta-Ureidovaleratea-amino-delta-Ureidovaleric acida-amino-g-Ureidovaleratea-amino-g-Ureidovaleric acida-amino-δ-Ureidovaleratea-amino-δ-Ureidovaleric acidAlpha-Amino-delta-ureidovalerateAlpha-Amino-delta-ureidovaleric acidAlpha-Amino-gamma-ureidovalerateAlpha-Amino-gamma-ureidovaleric acidAmino-ureidovalerateAmino-ureidovaleric acidCIRCITCitrullineCytrullineD-UreidonorvalineDelta-UreidonorvalineDL-citrullineGammaureidonorvalineH-Cit-ohL(+)-2-Amino-5-ureidovalerateL(+)-2-Amino-5-ureidovaleric acidL(+)-CitrullineL-2-Amino-5-ureido-valerateL-2-Amino-5-ureido-valeric acidL-2-Amino-5-ureidovalerateL-2-Amino-5-ureidovaleric acidL-CitrullineL-CytrullineL-N5-carbamoyl-OrnithineNγ-carbamylornithineN()-CarbamylornithineN(5)-(Aminocarbonyl)-DL-OrnithineN(delta)-CarbamylornithineN(δ)-CarbamylornithineN-CarbamylornithineN5-(Aminocarbonyl)-L-ornithineN5-(aminocarbonyl)-OrnithineN5-(Aminocarbonyl)ornithineN5-Carbamoyl-L-ornithineN5-carbamoylornithineN5-carbamylornithineN<sup>γ</sup>-carbamylornithineN<sup>5</sup>-(Aminocarbonyl)-L-ornithineN<SUP>5</SUP>-(aminocarbonyl)ornithineND-carbamylornithineNdelta-carbamy-ornithineNdelta-carbamylornithineNgamma-carbamylornithineSitrullineUreidonorvalineUreidovalerateUreidovaleric acidα-amino-γ-Ureidovalerateα-amino-γ-Ureidovaleric acidα-amino-δ-Ureidovalerateα-amino-δ-Ureidovaleric acidδ-UreidonorvalineC6H13N3O3175.1857175.095691297(2S)-2-amino-5-(carbamoylamino)pentanoic acidL-citrulline372-75-8N[C@@H](CCCNC(N)=O)C(O)=OInChI=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/s1RHGKLRLOHDJJDR-BYPYZUCNSA-NSolidCytosollogp-3.27logs-0.90solubility2.18e+01 g/lmelting_point235.5 oClogp-3.9pka_strongest_acidic2.27pka_strongest_basic9.23iupac(2S)-2-amino-5-(carbamoylamino)pentanoic acidaverage_mass175.1857mono_mass175.095691297smilesN[C@@H](CCCNC(N)=O)C(O)=OformulaC6H13N3O3inchiInChI=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/s1inchikeyRHGKLRLOHDJJDR-BYPYZUCNSA-Npolar_surface_area118.44refractivity41.33polarizability17.35rotatable_bond_count5acceptor_count4donor_count4physiological_charge0formal_charge0Alanine, aspartate and glutamate metabolismec00250Arginine and proline metabolismec00330Metabolic pathwayseco01100Aspartate metabolismAspartate (seen in the center) is synthesized from and degraded to oxaloacetate , an intermediate of the TCA cycle, by a reversible transamination reaction with glutamate. As shown here, AspC is the principal transaminase that catalyzes this reaction, but TyrB also catalyzes it. Null mutations in aspC do not confer aspartate auxotrophy; null mutations in both aspC and tyrB do.
Aspartate is a constituent of proteins and participates in several other biosyntheses as shown here( NAD biosynthesis and Beta-Alanine Metabolism . Approximately 27 percent of the cell's nitrogen flows through aspartate
Aspartate can be synthesized from fumaric acid through a aspartate ammonia lyase. Aspartate also participates in the synthesis of L-asparagine through two different methods, either through aspartate ammonia ligase or asparagine synthetase B.
Aspartate is also a precursor of fumaric acid. Again it has two possible ways of synthesizing it. First set of reactions follows an adenylo succinate synthetase that yields adenylsuccinic acid and then adenylosuccinate lyase in turns leads to fumaric acid. The second way is through argininosuccinate synthase that yields argininosuccinic acid and then argininosuccinate lyase in turns leads to fumaric acid
PW000787Metabolicarginine metabolismThe metabolism of L-arginine starts with the acetylation of L-glutamic acid resulting in a N-acetylglutamic acid while releasing a coenzyme A and a hydrogen ion. N-acetylglutamic acid is then phosphorylated via an ATP driven acetylglutamate kinase which yields a N-acetyl-L-glutamyl 5-phosphate. This compound undergoes a NDPH dependent reduction resulting in N-acetyl-L-glutamate 5-semialdehyde. This compound reacts with L-glutamic acid through a acetylornithine aminotransferase / N-succinyldiaminopimelate aminotransferase to produce a N-acetylornithine which is then deacetylated through a acetylornithine deacetylase which yield an ornithine.
L-glutamine is used to synthesize carbamoyl phosphate through the interaction of L-glutamine, water, ATP, and hydrogen carbonate. This reaction yields ADP, L-glutamic acid, phosphate, and hydrogen ion.
Carbamoyl phosphate and ornithine are used to catalyze the production of citrulline through an ornithine carbamoyltransferase. Citrulline reacts with L-aspartic acid through an ATP dependent enzyme, argininosuccinate synthase to produce pyrophosphate, AMP and argininosuccinic acid. Argininosussinic acid is then lyase to produce L-arginine and fumaric acid.
L-arginine can be metabolized into succinic acid by two different sets of reactions:
1. Arginine reacts with succinyl-CoA through a arginine N-succinyltransferase resulting in N2-succinyl-L-arginine while releasing CoA and Hydrogen Ion. N2-succinyl-L-arginine is then dihydrolase to produce a N2-succinyl-L-ornithine through a N-succinylarginine dihydrolase. This compound in turn reacts with oxoglutaric acid through succinylornithine transaminase resulting in L-glutamic acid and N2-succinyl-L-glutamic acid 5-semialdehyde. This compoud in turn reacts with a NAD dependent dehydrogenase resulting in N2-succinylglutamate while releasing NADH and hydrogen ion. N2-succinylglutamate reacts with water through a succinylglutamate desuccinylase resulting in L-glutamic acid and
a succinic acid. The succinic acid is then incorporated in the TCA cycle
2.Argine reacts with carbon dioxide and a hydrogen ion through a biodegradative arginine decarboxylase, resulting in Agmatine. This compound is then transformed into putrescine by reacting with water and an agmatinase, and releasing urea. Putrescine can be metabolized by reaction with either l-glutamic acid or oxoglutaric acid. If putrescine reacts with L-glutamic acid, it reacts through an ATP mediated gamma-glutamylputrescine producing a hydrogen ion, ADP, phosphate and gamma-glutamyl-L-putrescine. This compound is reduced by interacting with oxygen, water and a gamma-glutamylputrescine oxidoreductase resulting in ammonium, hydrogen peroxide and 4-gamma-glutamylamino butanal. This compound is dehydrogenated through a NADP mediated reaction lead by gamma-glutamyl-gamma-aminobutaryaldehyde dehydrogenase resulting in hydrogen ion, NADPH and 4-glutamylamino butanoate. In turn, the latter compound reacts with water through a gamma-glutamyl-gamma-aminobutyrate hydrolase resulting in L-glutamic acid and Gamma aminobutyric acid. On the other hand, if putrescine reacts with oxoglutaric acid through a putrescine aminotransferase, it results in L-glutamic acid, and a 4-aminobutyraldehyde. This compound reacts with water through a NAD dependent gamma aminobutyraldehyde dehydrogenase resulting in hydrogen ion, NADH and gamma-aminobutyric acid.
Gamma Aaminobutyric acid reacts with oxoglutaric acid through 4-aminobutyrate aminotransferase resulting in L-glutamic acid and succinic acid semialdehyde. This compound in turn can react with with either NADP or NAD to result in the production of succinic acid through succinate-semialdehyde dehydrogenase or aldehyde dehydrogenase-like protein yneI respectively. Succinic acid can then be integrated in the TCA cycle.
L-arginine is eventua lly metabolized into succinic acid which then goes to the TCA cyclePW000790Metabolicarginine biosynthesis IARGSYN-PWYSpecdb::CMs671Specdb::CMs1793Specdb::CMs3348Specdb::CMs30500Specdb::CMs31260Specdb::CMs37834Specdb::CMs137170Specdb::CMs144904Specdb::CMs1081335Specdb::CMs1081337Specdb::CMs1081339Specdb::CMs1081341Specdb::CMs1081342Specdb::CMs1081344Specdb::CMs1081346Specdb::NmrOneD1281Specdb::NmrOneD1596Specdb::NmrOneD4747Specdb::NmrOneD20982Specdb::NmrOneD20983Specdb::NmrOneD20984Specdb::NmrOneD20985Specdb::NmrOneD20986Specdb::NmrOneD20987Specdb::NmrOneD20988Specdb::NmrOneD20989Specdb::NmrOneD20990Specdb::NmrOneD20991Specdb::NmrOneD20992Specdb::NmrOneD20993Specdb::NmrOneD20994Specdb::NmrOneD20995Specdb::NmrOneD20996Specdb::NmrOneD20997Specdb::NmrOneD20998Specdb::NmrOneD20999Specdb::NmrOneD21000Specdb::NmrOneD21001Specdb::NmrOneD166430Specdb::MsMs1286Specdb::MsMs1287Specdb::MsMs1288Specdb::MsMs4843Specdb::MsMs4844Specdb::MsMs4845Specdb::MsMs4846Specdb::MsMs4847Specdb::MsMs4848Specdb::MsMs4849Specdb::MsMs4850Specdb::MsMs4851Specdb::MsMs4852Specdb::MsMs4853Specdb::MsMs4854Specdb::MsMs4855Specdb::MsMs4856Specdb::MsMs4857Specdb::MsMs4858Specdb::MsMs4859Specdb::MsMs4860Specdb::MsMs4861Specdb::MsMs4862Specdb::MsMs4863Specdb::MsMs4864Specdb::NmrTwoD1044Specdb::NmrTwoD1537HMDB0090497509367C0032718211L-CITRULLINECIRCitrullineKeseler, I. 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Applied Microbiology (1971), 22(6), 992-9.http://hmdb.ca/system/metabolites/msds/000/000/816/original/HMDB00904.pdf?1358463111Ornithine carbamoyltransferase chain IP04391OTC1_ECOLIargIhttp://ecmdb.ca/proteins/P04391.xmlOrnithine carbamoyltransferase chain FP06960OTC2_ECOLIargFhttp://ecmdb.ca/proteins/P06960.xmlArgininosuccinate synthaseP0A6E4ASSY_ECOLIargGhttp://ecmdb.ca/proteins/P0A6E4.xmlAcetylornithine deacetylaseP23908ARGE_ECOLIargEhttp://ecmdb.ca/proteins/P23908.xmlCarbamoylphosphate + Ornithine + L-Ornithine <> Citrulline + Hydrogen ion + PhosphateR01398ORNCARBAMTRANSFER-RXNL-Aspartic acid + Adenosine triphosphate + Citrulline <> Adenosine monophosphate + Argininosuccinic acid + Hydrogen ion + PyrophosphateR01954Carbamoylphosphate + Ornithine <> Phosphate + CitrullineR01398Adenosine triphosphate + Citrulline + L-Aspartic acid <> Adenosine monophosphate + Pyrophosphate + Argininosuccinic acidR01954N-Acetyl-L-citrulline + Water <> Acetic acid + CitrullineR09107L-Aspartic acid + Citrulline + Adenosine triphosphate > Hydrogen ion + L-arginino-succinate + Pyrophosphate + Adenosine monophosphateARGSUCCINSYN-RXNOrnithine + Carbamoylphosphate <> Hydrogen ion + Citrulline + PhosphateR01398ORNCARBAMTRANSFER-RXNAdenosine triphosphate + Citrulline + L-Aspartic acid > Adenosine monophosphate + Pyrophosphate + 2-(N(omega)-L-arginino)succinateCarbamoylphosphate + Ornithine > Inorganic phosphate + CitrullineAdenosine triphosphate + Citrulline + L-Aspartic acid + L-Aspartic acid > Pyrophosphate + Adenosine monophosphate + Argininosuccinic acidPW_R002649Ornithine + Carbamoylphosphate + Ornithine > Phosphate + Hydrogen ion + CitrullinePW_R002676L-Aspartic acid + Adenosine triphosphate + Citrulline <> Adenosine monophosphate + Argininosuccinic acid + Hydrogen ion + PyrophosphateCarbamoylphosphate + Ornithine + L-Ornithine <> Citrulline + Hydrogen ion + PhosphateL-Aspartic acid + Adenosine triphosphate + Citrulline <> Adenosine monophosphate + Argininosuccinic acid + Hydrogen ion + PyrophosphateGutnick 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 glucoseShake flask and filter culture1350.0uM0.037 oCK12 NCM3722Mid-Log Phase54000000Bennett, 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 5:593-599.19561621Gutnick 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 glycerolShake flask and filter culture931.0uM0.037 oCK12 NCM3722Mid-Log Phase37240000Bennett, 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 5:593-599.19561621Gutnick 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 acetateShake flask and filter culture516.0uM0.037 oCK12 NCM3722Mid-Log Phase20640000Bennett, 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 5:593-599.1956162148 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 GlucoBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h38.4uM0.037 oCBW25113Stationary Phase, glucose limited1536000Ishii, 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 316:593-597.17379776Luria-Bertani (LB) mediaShake flask269.67uMtrue13.5837 oCBL21 DE3Stationary phase cultures (overnight culture)107866754308Lin, Z., Johnson, L. C., Weissbach, H., Brot, N., Lively, M. O., Lowther, W. T. (2007). "Free methionine-(R)-sulfoxide reductase from Escherichia coli reveals a new GAF domain function." Proc Natl Acad Sci U S A 104:9597-9602.17535911