2.0 2012-10-10 12:17:18 -0600 2015-06-03 17:25:57 -0600 ECMDB23116 M2MDB003506 L-Methionine (R)-S-oxide L-Methionine (R)-S-oxide or Met-(R)-O is an oxidized form of methionine. It can be used as a substrate for growth by E. coli. It is known that Escherichia coli methionine mutants can grow on both enantiomers of methionine sulfoxide (met(o)), i.e., Met-R-(O) or Met-S-(O), indicating the presence of enzymes in E. coli that can reduce each of these enantiomers to methionine (met). Recently it was discovered that an enzyme known as fRMsr or L-methionine (R)-S-oxide reductase (EC 1.8.4.14) is the enzyme that catalyzes the chemical reaction L-methionine + thioredoxin disulfide + H2O <=> L-methionine (R)-S-oxide + thioredoxin. It is thought that Met-(R)-O may represent a signaling molecule in response to oxidative stress. [PMID:17535911] (2S)-2-amino-4-(R)-Methylsulfinylbutanoate (2S)-2-Amino-4-(R)-methylsulfinylbutanoic acid (2S)-2-amino-4-(R)-Methylsulphinylbutanoate (2S)-2-amino-4-(R)-Methylsulphinylbutanoic acid C5H11NO3S 165.211 165.045963913 (2S)-2-amino-4-[(R)-methanesulfinyl]butanoic acid L-methionine (R)-S-oxide C[S@@](=O)CC[C@H](N)C(O)=O InChI=1S/C5H11NO3S/c1-10(9)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-,10+/m0/s1 QEFRNWWLZKMPFJ-ZXPFJRLXSA-N logp -2.40 ALOGPS logs -0.49 ALOGPS solubility 5.40e+01 g/l ALOGPS logp -4.6 ChemAxon pka_strongest_acidic 1.74 ChemAxon pka_strongest_basic 9.11 ChemAxon iupac (2S)-2-amino-4-[(R)-methanesulfinyl]butanoic acid ChemAxon average_mass 165.211 ChemAxon mono_mass 165.045963913 ChemAxon smiles C[S@@](=O)CC[C@H](N)C(O)=O ChemAxon formula C5H11NO3S ChemAxon inchi InChI=1S/C5H11NO3S/c1-10(9)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-,10+/m0/s1 ChemAxon inchikey QEFRNWWLZKMPFJ-ZXPFJRLXSA-N ChemAxon polar_surface_area 80.39 ChemAxon refractivity 39.34 ChemAxon polarizability 16.08 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 2457 Specdb::NmrOneD 332898 Specdb::NmrOneD 332899 Specdb::NmrOneD 332900 Specdb::NmrOneD 332901 Specdb::NmrOneD 332902 Specdb::NmrOneD 332903 Specdb::NmrOneD 332904 Specdb::NmrOneD 332905 Specdb::NmrOneD 332906 Specdb::NmrOneD 332907 Specdb::NmrOneD 332908 Specdb::NmrOneD 332909 Specdb::NmrOneD 332910 Specdb::NmrOneD 332911 Specdb::NmrOneD 332912 Specdb::NmrOneD 332913 Specdb::NmrOneD 332914 Specdb::NmrOneD 332915 Specdb::NmrOneD 332916 Specdb::NmrOneD 332917 Specdb::MsMs 25496 Specdb::MsMs 25497 Specdb::MsMs 25498 Specdb::MsMs 32054 Specdb::MsMs 32055 Specdb::MsMs 32056 C15998 49032 SME L-Methionine + thioredoxin disulfide + Water > L-Methionine (R)-S-oxide + thioredoxin