2.0 2012-05-31 13:54:59 -0600 2015-09-13 12:56:12 -0600 ECMDB02005 M2MDB000428 Methionine sulfoxide Methionine sulfoxide is a member of the chemical class known as Alpha Amino Acids and Derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).Methionine is an amino acid susceptible to being oxidized to methionine sulfoxide (MetSO). The reduction of MetSO to methionine is catalyzed by methionine sulfoxide reductase (MSR), an enzyme present in almost all organisms. (PMID 20969952) Oxidation of methionine to methionine sulfoxide is a major oxidative stress product that reaches levels as high as 60% in cataract while being essentially absent from clear lenses. Methionine oxidation results in loss of protein function that can be reversed through the action of methionine sulfoxide reductase A (MsrA), which is implicated in oxidative stress protection and is an essential regulator of longevity in species ranging from Escherichia coli to mice. (PMID 15199188) A sulfenic acid enzyme intermediate is involved in the catalytic mechanism of peptide methionine sulfoxide reductase from Escherichia coli. (PMID 10964927) 2-amino-4-(methylsulfinyl)-Butanoate 2-amino-4-(methylsulfinyl)-Butanoic acid 2-amino-4-(Methylsulphinyl)-butanoate 2-amino-4-(Methylsulphinyl)-butanoic acid a-amino-g-(Methylsulfinyl)-butyrate a-amino-g-(Methylsulfinyl)-butyric acid a-amino-g-(Methylsulphinyl)-butyrate a-amino-g-(Methylsulphinyl)-butyric acid alpha-amino-gamma-(Methylsulfinyl)-butyrate Alpha-amino-gamma-(methylsulfinyl)-Butyric acid alpha-amino-gamma-(Methylsulphinyl)-butyrate alpha-amino-gamma-(Methylsulphinyl)-butyric acid DL-Methionine sulfoxide DL-Methionine sulphoxide H-Met(O)-OH L-methionine (S)-S-oxide L-methionine R-oxide L-Methionine sulfoxide L-Methionine sulfoxide 99+ L-Methionine sulphoxide L-Methionine sulphoxide 99+ L-METHIONINEsulfoxide L-METHIONINESULPHOXIDE Methionine S-oxide Methionine sulfoxide Methionine sulphoxide Methionine, S-oxide MetSFX S-oxide-methionine α-amino-γ-(Methylsulfinyl)-butyrate α-amino-γ-(Methylsulfinyl)-butyric acid α-amino-γ-(Methylsulphinyl)-butyrate α-amino-γ-(Methylsulphinyl)-butyric acid C5H11NO3S 165.211 165.045963913 (2S)-2-amino-4-methanesulfinylbutanoic acid L-methionine sulfoxide 62697-73-8 CS(=O)CCC(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) QEFRNWWLZKMPFJ-UHFFFAOYSA-N Solid Cytosol Extra-organism Periplasm logp -2.40 ALOGPS logs -0.49 ALOGPS solubility 5.40e+01 g/l ALOGPS melting_point 232 - 234 oC logp -4.6 ChemAxon pka_strongest_acidic 1.74 ChemAxon pka_strongest_basic 9.11 ChemAxon iupac (2S)-2-amino-4-methanesulfinylbutanoic acid ChemAxon average_mass 165.211 ChemAxon mono_mass 165.045963913 ChemAxon smiles CS(=O)CCC(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) ChemAxon inchikey QEFRNWWLZKMPFJ-UHFFFAOYSA-N ChemAxon polar_surface_area 80.39 ChemAxon refractivity 39.34 ChemAxon polarizability 15.98 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 102749 Specdb::CMs 102750 Specdb::CMs 102751 Specdb::CMs 102752 Specdb::CMs 102753 Specdb::CMs 102754 Specdb::CMs 102755 Specdb::CMs 102756 Specdb::CMs 131350 Specdb::CMs 139084 Specdb::NmrOneD 5212 Specdb::NmrOneD 5213 Specdb::NmrOneD 5214 Specdb::NmrOneD 10002 Specdb::NmrOneD 10003 Specdb::NmrOneD 10004 Specdb::NmrOneD 10005 Specdb::NmrOneD 10006 Specdb::NmrOneD 10007 Specdb::NmrOneD 10008 Specdb::NmrOneD 10009 Specdb::NmrOneD 10010 Specdb::NmrOneD 10011 Specdb::NmrOneD 10012 Specdb::NmrOneD 10013 Specdb::NmrOneD 10014 Specdb::NmrOneD 10015 Specdb::NmrOneD 10016 Specdb::NmrOneD 10017 Specdb::NmrOneD 10018 Specdb::NmrOneD 10019 Specdb::NmrOneD 10020 Specdb::NmrOneD 10021 Specdb::MsMs 1448443 Specdb::MsMs 1448444 Specdb::MsMs 1448445 Specdb::MsMs 2256718 Specdb::MsMs 2257857 Specdb::MsMs 2414998 Specdb::MsMs 2414999 Specdb::MsMs 2415000 Specdb::MsMs 2546901 Specdb::MsMs 2546902 Specdb::MsMs 2546903 Specdb::NmrTwoD 2042 HMDB02005 824 C02989 CPD0-1959 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. 21097882 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. 17765195 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. 18331064 Kantorow, M., Hawse, J. R., Cowell, T. L., Benhamed, S., Pizarro, G. O., Reddy, V. 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Anal Biochem. 2003 Feb 1;313(1):28-33. 12576054 http://hmdb.ca/system/metabolites/msds/000/001/588/original/HMDB02005.pdf?1358463056 Peptide methionine sulfoxide reductase msrA P0A744 MSRA_ECOLI msrA http://ecmdb.ca/proteins/P0A744.xml Peptide methionine sulfoxide reductase msrB P0A746 MSRB_ECOLI msrB http://ecmdb.ca/proteins/P0A746.xml Thioredoxin-2 P0AGG4 THIO2_ECOLI trxC http://ecmdb.ca/proteins/P0AGG4.xml Biotin sulfoxide reductase P20099 BISC_ECOLI bisC http://ecmdb.ca/proteins/P20099.xml Thioredoxin-1 P0AA25 THIO_ECOLI trxA http://ecmdb.ca/proteins/P0AA25.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 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 Methionine sulfoxide + Reduced Thioredoxin > Water + L-Methionine + Oxidized Thioredoxin Hydrogen peroxide + L-Methionine > Water + Methionine sulfoxide Luria-Bertani (LB) media Shake flask 6.84 uM true 0.57 37 oC BL21 DE3 Stationary phase cultures (overnight culture) 27373 2274 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