2.0 2012-05-31 10:22:52 -0600 2015-09-13 12:56:06 -0600 ECMDB00172 M2MDB000071 L-Isoleucine Isoleucine is an amino acid with the chemical formula HO2CCH(NH2)CH(CH3)CH2CH3. Its codons are AUU, AUC and AUA. With a hydrocarbon side chain, isoleucine is classified as a hydrophobic amino acid. Together with threonine, isoleucine is one of two common amino acids that have a chiral side chain. Four stereoisomers of isoleucine are possible, including two possible diastereomers of L-isoleucine. However, isoleucine present in nature exists in one enantiomeric form, (2S,3S)-2-amino-3-methylpentanoic acid. (Wikipedia) (2S,3S)-2-amino-3-methyl-Pentanoate (2S,3S)-2-amino-3-methyl-Pentanoic acid (2S,3S)-2-Amino-3-methylpentanoate (2S,3S)-2-Amino-3-methylpentanoic acid (2S,3S)-a-amino-b-Merthyl-N-valerate (2S,3S)-a-amino-b-Merthyl-N-valeric acid (2S,3S)-a-amino-b-Merthylvalerate (2S,3S)-a-amino-b-Merthylvaleric acid (2S,3S)-a-Amino-b-methyl-N-valerate (2S,3S)-a-Amino-b-methyl-N-valeric acid (2S,3S)-a-Amino-b-methylvalerate (2S,3S)-a-Amino-b-methylvaleric acid (2S,3S)-a-Amino-beta-methylvalerate (2S,3S)-a-Amino-beta-methylvaleric acid (2S,3S)-a-amino-β-Methylvalerate (2S,3S)-a-amino-β-Methylvaleric acid (2S,3S)-Alph-amino-b-methylvalerate (2S,3S)-Alph-amino-b-methylvaleric acid (2S,3S)-alph-Amino-beta-methylvalerate (2S,3S)-alph-Amino-beta-methylvaleric acid (2S,3S)-Alph-amino-β-methylvalerate (2S,3S)-Alph-amino-β-methylvaleric acid (2S,3S)-alpha-Amino-b-methyl-N-valerate (2S,3S)-alpha-Amino-b-methyl-N-valeric acid (2S,3S)-alpha-Amino-b-methylvalerate (2S,3S)-alpha-Amino-b-methylvaleric acid (2S,3S)-alpha-Amino-beta-merthyl-n-valerate (2S,3S)-alpha-Amino-beta-merthyl-n-valeric acid (2S,3S)-alpha-Amino-beta-merthylvalerate (2S,3S)-alpha-Amino-beta-merthylvaleric acid (2S,3S)-alpha-Amino-beta-methyl-N-valerate (2S,3S)-alpha-Amino-beta-methyl-N-valeric acid (2S,3S)-alpha-Amino-beta-methylvalerate (2S,3S)-alpha-Amino-beta-methylvaleric acid (2S,3S)-α-amino-b-Methyl-N-valerate (2S,3S)-α-amino-b-Methyl-N-valeric acid (2S,3S)-α-amino-b-Methylvalerate (2S,3S)-α-amino-b-Methylvaleric acid (2S,3S)-α-amino-β-Merthyl-N-valerate (2S,3S)-α-amino-β-Merthyl-N-valeric acid (2S,3S)-α-amino-β-Merthylvalerate (2S,3S)-α-amino-β-Merthylvaleric acid (2S,3S)-α-amino-β-Methyl-N-valerate (2S,3S)-α-amino-β-Methyl-N-valeric acid (2S,3S)-α-amino-β-Methylvalerate (2S,3S)-α-amino-β-Methylvaleric acid (S)-Isoleucine (S,S)-Isoleucine 2-Amino-3-methylpentanoate 2-Amino-3-methylpentanoic acid 2-Amino-3-methylvalerate 2-Amino-3-methylvaleric acid 2S,3S-Isoleucine Erythro-L-Isoleucine I Ile Iso-leucine Isoleucine L-(+)-Isoleucine L-Ile [S-(R*,R*)]-2-Amino-3-methylpentanoate [S-(R*,R*)]-2-Amino-3-methylpentanoic acid C6H13NO2 131.1729 131.094628665 (2S,3S)-2-amino-3-methylpentanoic acid L-isoleucine 73-32-5 CC[C@H](C)[C@H](N)C(O)=O InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5-/m0/s1 AGPKZVBTJJNPAG-WHFBIAKZSA-N Solid Cytosol Extra-organism Periplasm logp -1.73 ALOGPS logs -0.06 ALOGPS solubility 1.14e+02 g/l ALOGPS melting_point 285.5 oC logp -1.5 ChemAxon pka_strongest_acidic 2.79 ChemAxon pka_strongest_basic 9.59 ChemAxon iupac (2S,3S)-2-amino-3-methylpentanoic acid ChemAxon average_mass 131.1729 ChemAxon mono_mass 131.094628665 ChemAxon smiles CC[C@H](C)[C@H](N)C(O)=O ChemAxon formula C6H13NO2 ChemAxon inchi InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5-/m0/s1 ChemAxon inchikey AGPKZVBTJJNPAG-WHFBIAKZSA-N ChemAxon polar_surface_area 63.32 ChemAxon refractivity 34.09 ChemAxon polarizability 14.11 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Valine, leucine and isoleucine biosynthesis ec00290 Aminoacyl-tRNA biosynthesis ec00970 Valine, leucine and isoleucine degradation ec00280 ABC transporters ec02010 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 isoleucine biosynthesis I (from threonine) ILEUSYN-PWY tRNA charging TRNA-CHARGING-PWY Specdb::CMs 410 Specdb::CMs 411 Specdb::CMs 412 Specdb::CMs 413 Specdb::CMs 414 Specdb::CMs 2741 Specdb::CMs 30031 Specdb::CMs 30374 Specdb::CMs 30375 Specdb::CMs 30376 Specdb::CMs 30599 Specdb::CMs 30727 Specdb::CMs 30793 Specdb::CMs 32117 Specdb::CMs 32316 Specdb::CMs 37336 Specdb::CMs 154007 Specdb::CMs 1052684 Specdb::CMs 1052685 Specdb::CMs 1052687 Specdb::EiMs 1294 Specdb::NmrOneD 1136 Specdb::NmrOneD 1189 Specdb::NmrOneD 3304 Specdb::NmrOneD 5972 Specdb::NmrOneD 5973 Specdb::NmrOneD 5974 Specdb::NmrOneD 5975 Specdb::NmrOneD 5976 Specdb::NmrOneD 5977 Specdb::NmrOneD 5978 Specdb::NmrOneD 5979 Specdb::NmrOneD 5980 Specdb::NmrOneD 5981 Specdb::NmrOneD 5982 Specdb::NmrOneD 5983 Specdb::NmrOneD 5984 Specdb::NmrOneD 5985 Specdb::NmrOneD 5986 Specdb::NmrOneD 5987 Specdb::NmrOneD 5988 Specdb::NmrOneD 5989 Specdb::NmrOneD 5990 Specdb::NmrOneD 5991 Specdb::NmrOneD 166474 Specdb::MsMs 271 Specdb::MsMs 272 Specdb::MsMs 273 Specdb::MsMs 3317 Specdb::MsMs 3318 Specdb::MsMs 3319 Specdb::MsMs 3320 Specdb::MsMs 3321 Specdb::MsMs 3322 Specdb::MsMs 3323 Specdb::MsMs 3324 Specdb::MsMs 3325 Specdb::MsMs 3326 Specdb::MsMs 3327 Specdb::MsMs 3328 Specdb::MsMs 3329 Specdb::MsMs 3330 Specdb::MsMs 3331 Specdb::MsMs 3332 Specdb::MsMs 3333 Specdb::MsMs 3334 Specdb::MsMs 3340 Specdb::MsMs 178770 Specdb::MsMs 178771 Specdb::MsMs 178772 Specdb::NmrTwoD 981 Specdb::NmrTwoD 1185 HMDB00172 791 6067 C00407 17191 ILE ILE_LFZW Ile Keseler, I. 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Organic Syntheses (1941), 21 60-4. http://hmdb.ca/system/metabolites/msds/000/000/121/original/HMDB00172.pdf?1358894678 Isoleucyl-tRNA synthetase P00956 SYI_ECOLI ileS http://ecmdb.ca/proteins/P00956.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 Branched-chain-amino-acid aminotransferase P0AB80 ILVE_ECOLI ilvE http://ecmdb.ca/proteins/P0AB80.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 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 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 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 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 Branched-chain amino acid transport system 2 carrier protein P0AD99 BRNQ_ECOLI brnQ http://ecmdb.ca/proteins/P0AD99.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Adenosine triphosphate + Water + L-Isoleucine > ADP + Hydrogen ion + L-Isoleucine + Phosphate ABC-15-RXN Adenosine triphosphate + Water + L-Isoleucine > ADP + Hydrogen ion + L-Isoleucine + Phosphate ABC-15-RXN Adenosine triphosphate + L-Isoleucine + tRNA(Ile) + tRNA(Ile) <> Adenosine monophosphate + L-Isoleucyl-tRNA(Ile) + Pyrophosphate + L-Isoleucyl-tRNA(Ile) R03656 alpha-Ketoglutarate + L-Isoleucine <> 3-Methyl-2-oxovaleric acid + L-Glutamate R02199 Adenosine triphosphate + L-Isoleucine + tRNA(Ile) <> Adenosine monophosphate + Pyrophosphate + L-Isoleucyl-tRNA(Ile) R03656 Adenosine triphosphate + L-Isoleucine + Water > ADP + Phosphate + L-Isoleucine + Hydrogen ion ABC-15-RXN Adenosine triphosphate + L-Isoleucine + Water > ADP + Phosphate + L-Isoleucine + Hydrogen ion ABC-15-RXN L-Isoleucine + Oxoglutaric acid <> 3-Methyl-2-oxovaleric acid + L-Glutamate BRANCHED-CHAINAMINOTRANSFERILEU-RXN L-Isoleucine + Oxoglutaric acid > (S)-3-methyl-2-oxopentanoate + L-Glutamate Adenosine triphosphate + L-Isoleucine + tRNA(Ile) > Adenosine monophosphate + Pyrophosphate + L-isoleucyl-tRNA(Ile) L-Isoleucine + Adenosine triphosphate + Hydrogen ion + tRNA(Ile) + L-Isoleucine > L-Isoleucyl-tRNA(Ile) + Adenosine monophosphate + Pyrophosphate PW_R002832 3-Methyl-2-oxovaleric acid + L-Glutamic acid + 3-Methyl-2-oxovaleric acid + L-Glutamate > Oxoglutaric acid + L-Isoleucine + L-Isoleucine PW_R002928 L-Isoleucine + Adenosine triphosphate + Water + L-Isoleucine > L-Isoleucine + Adenosine diphosphate + Phosphate + Hydrogen ion + ADP PW_RCT000106 Adenosine triphosphate + L-Isoleucine + tRNA(Ile) <> Adenosine monophosphate + L-Isoleucyl-tRNA(Ile) + Pyrophosphate alpha-Ketoglutarate + L-Isoleucine <>3 3-Methyl-2-oxovaleric acid + L-Glutamate Adenosine triphosphate + L-Isoleucine + tRNA(Ile) <> Adenosine monophosphate + L-Isoleucyl-tRNA(Ile) + Pyrophosphate 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 150.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 600000 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 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 Shake flask and filter culture 220.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 880000 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 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 Shake flask and filter culture 170.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 680000 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 33.1 uM 0.0 37 oC BW25113 Stationary Phase, glucose limited 132400 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 172.0 uM true 23.0 37 oC BL21 DE3 Stationary phase cultures (overnight culture) 687600 92000 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 Luria-Bertani (LB) media Shake flask 178.0 uM true 23.26 37 oC BL21 DE3 Stationary phase cultures (overnight culture) 712000 93038 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