2.0 2012-05-31 10:22:41 -0600 2015-09-13 12:56:06 -0600 ECMDB00167 M2MDB000068 L-Threonine Threonine is an amino acid. It is converted to pyruvate via threonine dehydrogenase. An intermediate in this pathway can undergo thiolysis with CoA to produce acetyl-CoA and glycine. (Wikipedia) (2S,3R)-(-)-Threonine (2S,3R)-2-Amino-3-hydroxybutyrate (2S,3R)-2-Amino-3-hydroxybutyric acid (R-(R*,S*))-2-Amino-3-hydroxybutanoate (R-(R*,S*))-2-Amino-3-hydroxybutanoic acid (S)-Threonine 2-Amino-3-hydroxybutanoate 2-Amino-3-hydroxybutanoic acid 2-Amino-3-hydroxybutyrate 2-Amino-3-hydroxybutyric acid L-(-)-Threonine L-2-Amino-3-hydroxybutyrate L-2-Amino-3-hydroxybutyric acid L-a-amino-b-Hydroxybutyrate L-a-amino-b-Hydroxybutyric acid L-alpha-Amino-beta-hydroxybutyrate L-alpha-Amino-beta-hydroxybutyric acid L-thr L-α-amino-β-Hydroxybutyrate L-α-amino-β-Hydroxybutyric acid T Thr Thre Threonin Threonine [R-(R*,S*)]-2-amino-3-hydroxy-Butanoate [R-(R*,S*)]-2-amino-3-hydroxy-Butanoic acid [R-(R*,S*)]-2-Amino-3-hydroxybutanoate [R-(R*,S*)]-2-Amino-3-hydroxybutanoic acid C4H9NO3 119.1192 119.058243159 (2S,3R)-2-amino-3-hydroxybutanoic acid L-threonine 72-19-5 C[C@@H](O)[C@H](N)C(O)=O InChI=1S/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3+/m1/s1 AYFVYJQAPQTCCC-GBXIJSLDSA-N Solid Cytosol Extra-organism Periplasm logp -3.01 ALOGPS logs 0.60 ALOGPS solubility 4.77e+02 g/l ALOGPS melting_point 256 oC logp -3.5 ChemAxon pka_strongest_acidic 2.21 ChemAxon pka_strongest_basic 9 ChemAxon iupac (2S,3R)-2-amino-3-hydroxybutanoic acid ChemAxon average_mass 119.1192 ChemAxon mono_mass 119.058243159 ChemAxon smiles C[C@@H](O)[C@H](N)C(O)=O ChemAxon formula C4H9NO3 ChemAxon inchi InChI=1S/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3+/m1/s1 ChemAxon inchikey AYFVYJQAPQTCCC-GBXIJSLDSA-N ChemAxon polar_surface_area 83.55 ChemAxon refractivity 26.46 ChemAxon polarizability 11.08 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Glycine, serine and threonine metabolism ec00260 Valine, leucine and isoleucine biosynthesis ec00290 Vitamin B6 metabolism ec00750 Aminoacyl-tRNA biosynthesis ec00970 Porphyrin and chlorophyll metabolism ec00860 Propanoate metabolism Starting from L-threonine, this compound is deaminated through a threonine deaminase resulting in a hydrogen ion, a water molecule and a (2z)-2-aminobut-2-enoate. The latter compound then isomerizes to a 2-iminobutanoate, This compound then reacts spontaneously with hydrogen ion and a water molecule resulting in a ammonium and a 2-Ketobutyric acid. The latter compound interacts with CoA through a pyruvate formate-lyase / 2-ketobutyrate formate-lyase resulting in a formic acid and a propionyl-CoA. Propionyl-CoA can then be processed either into a 2-methylcitric acid or into a propanoyl phosphate. Propionyl-CoA interacts with oxalacetic acid and a water molecule through a 2-methylcitrate synthase resulting in a hydrogen ion, a CoA and a 2-Methylcitric acid.The latter compound is dehydrated through a 2-methylcitrate dehydratase resulting in a water molecule and cis-2-methylaconitate. The latter compound is then dehydrated by a bifunctional aconitate hydratase 2 and 2-methylisocitrate dehydratase resulting in a water molecule and methylisocitric acid. The latter compound is then processed by 2-methylisocitrate lyase resulting in a release of succinic acid and pyruvic acid. Succinic acid can then interact with a propionyl-CoA through a propionyl-CoA:succinate CoA transferase resulting in a propionic acid and a succinyl CoA. Succinyl-CoA is then isomerized through a methylmalonyl-CoA mutase resulting in a methylmalonyl-CoA. This compound is then decarboxylated through a methylmalonyl-CoA decarboxylase resulting in a release of Carbon dioxide and Propionyl-CoA. ropionyl-CoA interacts with a phosphate through a phosphate acetyltransferase / phosphate propionyltransferase resulting in a CoA and a propanoyl phosphate. Propionyl-CoA can react with a phosphate through a phosphate acetyltransferase / phosphate propionyltransferase resulting in a CoA and a propanoyl phosphate. The latter compound is then dephosphorylated through a ADP driven acetate kinase/propionate kinase protein complex resulting in an ATP and Propionic acid. Propionic acid can be processed by a reaction with CoA through a ATP-driven propionyl-CoA synthetase resulting in a pyrophosphate, an AMP and a propionyl-CoA. PW000940 ec00640 Metabolic Microbial metabolism in diverse environments ec01120 ABC transporters ec02010 Metabolic pathways eco01100 Secondary Metabolites: threonine biosynthesis from aspartate The biosynthesis of threonine starts with L-aspartic acid being phosphorylated by an ATP driven Aspartate kinase resulting in an a release of an ADP and an L-aspartyl-4-phosphate. This compound interacts with a hydrogen ion through an NADPH driven aspartate semialdehyde dehydrogenase resulting in the release of a phosphate, an NADP and a L-aspartate-semialdehyde.The latter compound interacts with a hydrogen ion through a NADPH driven aspartate kinase / homoserine dehydrogenase resulting in the release of an NADP and a L-homoserine. L-homoserine is phosphorylated through an ATP driven homoserine kinase resulting in the release of an ADP, a hydrogen ion and a O-phosphohomoserine. The latter compound then interacts with a water molecule threonine synthase resulting in the release of a phosphate and an L-threonine. PW000976 Metabolic inner membrane transport list of inner membrane transport complexes, transporting compounds from the periplasmic space to the cytosol This pathway should be updated regularly with the new inner membrae transports added PW000786 Metabolic isoleucine biosynthesis Isoleucine biosynthesis begins with L-threonine from the threonine biosynthesis pathway. L-threonine interacts with a threonine dehydratase biosynthetic releasing water, a hydrogen ion and (2Z)-2-aminobut-2-enoate. This compound is isomerized into a 2-iminobutanoate which interacts with water and a hydrogen ion spontaneously, resulting in the release of ammonium and 2-ketobutyric acid. This compound reacts with pyruvic acid and hydrogen ion through an acetohydroxybutanoate synthase / acetolactate synthase 2 resulting in carbon dioxide and (S)-2-Aceto-2-hydroxybutanoic acid. The latter compound is reduced by an NADPH driven acetohydroxy acid isomeroreductase releasing NADP and acetohydroxy acid isomeroreductase. The latter compound is dehydrated by a dihydroxy acid dehydratase resulting in 3-methyl-2-oxovaleric acid.This compound reacts in a reversible reaction with L-glutamic acid through a Branched-chain-amino-acid aminotransferase resulting in oxoglutaric acid and L-isoleucine. L-isoleucine can also be transported into the cytoplasm through two different methods: a branched chain amino acid ABC transporter or a branched chain amino acid transporter BrnQ y. PW000818 Metabolic tRNA Charging 2 This pathway groups together all E. coli tRNA charging reactions. PW000803 Metabolic tRNA charging This pathway groups together all E. coli tRNA charging reactions. PW000799 Metabolic threonine biosynthesis The biosynthesis of threonine starts with oxalacetic acid interacting with an L-glutamic acid through an aspartate aminotransferase resulting in a oxoglutaric acid and an L-aspartic acid. The latter compound is then phosphorylated by an ATP driven Aspartate kinase resulting in an a release of an ADP and an L-aspartyl-4-phosphate. This compound interacts with a hydrogen ion through an NADPH driven aspartate semialdehyde dehydrogenase resulting in the release of a phosphate, an NADP and a L-aspartate-semialdehyde.The latter compound interacts with a hydrogen ion through a NADPH driven aspartate kinase / homoserine dehydrogenase resulting in the release of an NADP and a L-homoserine. L-homoserine is phosphorylated through an ATP driven homoserine kinase resulting in the release of an ADP, a hydrogen ion and a O-phosphohomoserine. The latter compound then interacts with a water molecule threonine synthase resulting in the release of a phosphate and an L-threonine. PW000817 Metabolic L-threonine degradation to methylglyoxal L-threonine is degrade into methylglyoxal (pyruvaldehyde) by first reacting with a NDA dependent threonine dehydrogenase resulting in the release of a hydrogen ion, an NADH and a 2-amino-3-oxobutanoate. The latter compound reacts spontaneously with a hydrogen ion resulting in the release of a carbon dioxide and a aminoacetone. The aminoacetone in turn reacts with an oxygen and a water molecule through an aminoacetone oxidase resulting in the release of a hydrogen peroxide, ammonium and a methylglyoxal which can then be incorporated in the methylglyoxal degradation pathways. PW002106 Metabolic isoleucine biosynthesis I (from threonine) ILEUSYN-PWY threonine degradation I PWY-5437 tRNA charging TRNA-CHARGING-PWY threonine degradation III (to methylglyoxal) THRDLCTCAT-PWY threonine degradation II THREONINE-DEG2-PWY threonine degradation IV PWY-5436 threonine biosynthesis from homoserine HOMOSER-THRESYN-PWY Specdb::CMs 399 Specdb::CMs 400 Specdb::CMs 1025 Specdb::CMs 1090 Specdb::CMs 2588 Specdb::CMs 30052 Specdb::CMs 30053 Specdb::CMs 30382 Specdb::CMs 30613 Specdb::CMs 30728 Specdb::CMs 31038 Specdb::CMs 31039 Specdb::CMs 37333 Specdb::CMs 170648 Specdb::CMs 1052537 Specdb::CMs 1052539 Specdb::CMs 1052541 Specdb::CMs 1052542 Specdb::CMs 1052544 Specdb::CMs 1052546 Specdb::CMs 1052548 Specdb::CMs 1052550 Specdb::CMs 1052552 Specdb::CMs 1052553 Specdb::CMs 1052555 Specdb::NmrOneD 1129 Specdb::NmrOneD 1184 Specdb::NmrOneD 4794 Specdb::NmrOneD 142650 Specdb::NmrOneD 142651 Specdb::NmrOneD 142652 Specdb::NmrOneD 142653 Specdb::NmrOneD 142654 Specdb::NmrOneD 142655 Specdb::NmrOneD 142656 Specdb::NmrOneD 142657 Specdb::NmrOneD 142658 Specdb::NmrOneD 142659 Specdb::NmrOneD 142660 Specdb::NmrOneD 142661 Specdb::NmrOneD 142662 Specdb::NmrOneD 142663 Specdb::NmrOneD 142664 Specdb::NmrOneD 142665 Specdb::NmrOneD 142666 Specdb::NmrOneD 142667 Specdb::NmrOneD 142668 Specdb::NmrOneD 142669 Specdb::NmrOneD 166491 Specdb::MsMs 263 Specdb::MsMs 264 Specdb::MsMs 265 Specdb::MsMs 3258 Specdb::MsMs 3259 Specdb::MsMs 3260 Specdb::MsMs 3261 Specdb::MsMs 3262 Specdb::MsMs 3263 Specdb::MsMs 3264 Specdb::MsMs 3265 Specdb::MsMs 3266 Specdb::MsMs 3267 Specdb::MsMs 3268 Specdb::MsMs 3269 Specdb::MsMs 3270 Specdb::MsMs 3271 Specdb::MsMs 3272 Specdb::MsMs 3273 Specdb::MsMs 3274 Specdb::MsMs 3275 Specdb::MsMs 3276 Specdb::MsMs 3277 Specdb::MsMs 3278 Specdb::MsMs 178482 Specdb::NmrTwoD 979 Specdb::NmrTwoD 1182 HMDB00167 6288 6051 C00188 16857 THR THR_LFZW_DHG1 L-Threonine Keseler, I. 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Nippon Nogei Kagaku Kaishi (1965), 39(6), 2 http://hmdb.ca/system/metabolites/msds/000/000/117/original/HMDB00167.pdf?1358894693 Threonine synthase P00934 THRC_ECOLI thrC http://ecmdb.ca/proteins/P00934.xml Threonine dehydratase biosynthetic P04968 THD1_ECOLI ilvA http://ecmdb.ca/proteins/P04968.xml L-threonine 3-dehydrogenase P07913 TDH_ECOLI tdh http://ecmdb.ca/proteins/P07913.xml Serine hydroxymethyltransferase P0A825 GLYA_ECOLI glyA http://ecmdb.ca/proteins/P0A825.xml Threonyl-tRNA synthetase P0A8M3 SYT_ECOLI thrS http://ecmdb.ca/proteins/P0A8M3.xml Class B acid phosphatase P0AE22 APHA_ECOLI aphA http://ecmdb.ca/proteins/P0AE22.xml Threonine dehydratase catabolic P0AGF6 THD2_ECOLI tdcB http://ecmdb.ca/proteins/P0AGF6.xml Low specificity L-threonine aldolase P75823 LTAE_ECOLI ltaE http://ecmdb.ca/proteins/P75823.xml High-affinity branched-chain amino acid transport system permease protein livH P0AEX7 LIVH_ECOLI livH http://ecmdb.ca/proteins/P0AEX7.xml High-affinity branched-chain amino acid transport system permease protein livM P22729 LIVM_ECOLI livM http://ecmdb.ca/proteins/P22729.xml High-affinity branched-chain amino acid transport ATP-binding protein livG P0A9S7 LIVG_ECOLI livG http://ecmdb.ca/proteins/P0A9S7.xml Leu/Ile/Val-binding protein P0AD96 LIVJ_ECOLI livJ http://ecmdb.ca/proteins/P0AD96.xml High-affinity branched-chain amino acid transport ATP-binding protein livF P22731 LIVF_ECOLI livF http://ecmdb.ca/proteins/P22731.xml Threonylcarbamoyl-AMP synthase P45748 TSAC_ECOLI tsaC http://ecmdb.ca/proteins/P45748.xml Uncharacterized amino-acid ABC transporter ATP-binding protein yecC P37774 YECC_ECOLI yecC http://ecmdb.ca/proteins/P37774.xml Inner membrane amino-acid ABC transporter permease protein yecS P0AFT2 YECS_ECOLI yecS http://ecmdb.ca/proteins/P0AFT2.xml Threonine/serine transporter tdcC B1XGT1 TDCC_ECODH tdcC http://ecmdb.ca/proteins/B1XGT1.xml Threonine/serine transporter tdcC C4ZR30 TDCC_ECOBW tdcC http://ecmdb.ca/proteins/C4ZR30.xml Inner membrane transporter rhtA P0AA67 RHTA_ECOLI rhtA http://ecmdb.ca/proteins/P0AA67.xml Threonine/serine transporter tdcC P0AAD8 TDCC_ECOLI tdcC http://ecmdb.ca/proteins/P0AAD8.xml High-affinity branched-chain amino acid transport system permease protein livH P0AEX7 LIVH_ECOLI livH http://ecmdb.ca/proteins/P0AEX7.xml Serine/threonine transporter sstT P0AGE4 SSTT_ECOLI sstT http://ecmdb.ca/proteins/P0AGE4.xml High-affinity branched-chain amino acid transport system permease protein livM P22729 LIVM_ECOLI livM http://ecmdb.ca/proteins/P22729.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml High-affinity branched-chain amino acid transport ATP-binding protein livG P0A9S7 LIVG_ECOLI livG http://ecmdb.ca/proteins/P0A9S7.xml Threonine efflux protein P0AG38 RHTC_ECOLI rhtC http://ecmdb.ca/proteins/P0AG38.xml Leu/Ile/Val-binding protein P0AD96 LIVJ_ECOLI livJ http://ecmdb.ca/proteins/P0AD96.xml High-affinity branched-chain amino acid transport ATP-binding protein livF P22731 LIVF_ECOLI livF http://ecmdb.ca/proteins/P22731.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml L-Threonine <> Acetaldehyde + Glycine R00751 THREONINE-ALDOLASE-RXN L-Threonine > 2-Ketobutyric acid + Ammonium Adenosine triphosphate + Water + L-Threonine > ADP + Hydrogen ion + Phosphate + L-Threonine Adenosine triphosphate + Water + L-Threonine > ADP + Hydrogen ion + Phosphate + L-Threonine Water + O-Phosphohomoserine <> Phosphate + L-Threonine R01466 THRESYN-RXN Adenosine triphosphate + L-Threonine + tRNA(Thr) + tRNA(Thr) <> Adenosine monophosphate + Pyrophosphate + L-Threonyl-tRNA(Thr) + L-Threonyl-tRNA(Thr) R03663 NAD + L-Threonine <> L-2-Amino-3-oxobutanoic acid + Hydrogen ion + NADH R01465 THREODEHYD-RXN Water + L-Threonine O-3-phosphate > Phosphate + L-Threonine L-Threonine <> 2-Ketobutyric acid + Ammonia R00996 Adenosine triphosphate + L-Threonine + tRNA(Thr) <> Adenosine monophosphate + Pyrophosphate + L-Threonyl-tRNA(Thr) R03663 ala-thr + Water > L-Alanine + L-Threonine RXN0-6980 L-Threonine > Hydrogen ion + 2-Ketobutyric acid + Ammonia R00996 THREDEHYD-RXN L-Threonine + NAD > Hydrogen ion + L-2-Amino-3-oxobutanoic acid + NADH THREODEHYD-RXN L-Threonine > Acetaldehyde + Glycine THREONINE-ALDOLASE-RXN O-Phosphohomoserine + Water > Phosphate + L-Threonine R01466 THRESYN-RXN L-Threonine > 2-Ketobutyric acid + Ammonia R00996 THREDEHYD-RXN Adenosine triphosphate + L-Threonine + tRNA(Thr) > Adenosine monophosphate + Pyrophosphate + L-threonyl-tRNA(Thr) L-Threonine + NAD > L-2-Amino-3-oxobutanoic acid + NADH O-Phosphohomoserine + Water > L-Threonine + Inorganic phosphate L-Threonine + 2-Aminobut-2-enoate + 2-Iminobutanoate + Water <> 2-Ketobutyric acid + Ammonia R00996 L-Threonine + Adenosine triphosphate + Hydrogen carbonate <> L-Threonylcarbamoyladenylate + Pyrophosphate + Water R10463 L-Threonine + Adenosine triphosphate + Hydrogen ion + tRNA(Thr) + L-Threonine > Pyrophosphate + Adenosine monophosphate + L-Threonyl-tRNA(Thr) PW_R002829 O-Phosphohomoserine + Water > Phosphate + L-Threonine + L-Threonine PW_R002921 L-Threonine + L-Threonine > Hydrogen ion + Water + (2Z)-2-aminobut-2-enoate PW_R002922 L-Threonine + NAD + L-Threonine > Hydrogen ion + NADH + L-2-Amino-3-oxobutanoic acid PW_R005168 L-Threonine + Adenosine triphosphate + Hydrogen carbonate <> L-Threonylcarbamoyladenylate + Pyrophosphate + Water L-Threonine <> Acetaldehyde + Glycine Adenosine triphosphate + L-Threonine + tRNA(Thr) <> Adenosine monophosphate + Pyrophosphate + L-Threonyl-tRNA(Thr) Water + O-Phosphohomoserine <> Phosphate + L-Threonine 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 Shake flask and filter culture 179.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 716000 0 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. 19561621 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 Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h 147.0 uM 0.0 37 oC BW25113 Stationary Phase, glucose limited 588000 0 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. 17379776 Luria-Bertani (LB) media Shake flask 125.67 uM true 1.21 37 oC BL21 DE3 Stationary phase cultures (overnight culture) 502667 4839 Lin, 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