2.02012-05-31 13:54:59 -06002015-09-13 12:56:12 -0600ECMDB02005M2MDB000428Methionine sulfoxideMethionine 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)-Butanoate2-amino-4-(methylsulfinyl)-Butanoic acid2-amino-4-(Methylsulphinyl)-butanoate2-amino-4-(Methylsulphinyl)-butanoic acida-amino-g-(Methylsulfinyl)-butyratea-amino-g-(Methylsulfinyl)-butyric acida-amino-g-(Methylsulphinyl)-butyratea-amino-g-(Methylsulphinyl)-butyric acidalpha-amino-gamma-(Methylsulfinyl)-butyrateAlpha-amino-gamma-(methylsulfinyl)-Butyric acidalpha-amino-gamma-(Methylsulphinyl)-butyratealpha-amino-gamma-(Methylsulphinyl)-butyric acidDL-Methionine sulfoxideDL-Methionine sulphoxideH-Met(O)-OHL-methionine (S)-S-oxideL-methionine R-oxideL-Methionine sulfoxideL-Methionine sulfoxide 99+L-Methionine sulphoxideL-Methionine sulphoxide 99+L-METHIONINEsulfoxideL-METHIONINESULPHOXIDEMethionine S-oxideMethionine sulfoxideMethionine sulphoxideMethionine, S-oxideMetSFXS-oxide-methionineα-amino-γ-(Methylsulfinyl)-butyrateα-amino-γ-(Methylsulfinyl)-butyric acidα-amino-γ-(Methylsulphinyl)-butyrateα-amino-γ-(Methylsulphinyl)-butyric acidC5H11NO3S165.211165.045963913(2S)-2-amino-4-methanesulfinylbutanoic acidL-methionine sulfoxide62697-73-8CS(=O)CCC(N)C(O)=OInChI=1S/C5H11NO3S/c1-10(9)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)QEFRNWWLZKMPFJ-UHFFFAOYSA-NSolidCytosolExtra-organismPeriplasmlogp-2.40logs-0.49solubility5.40e+01 g/lmelting_point232 - 234 oClogp-4.6pka_strongest_acidic1.74pka_strongest_basic9.11iupac(2S)-2-amino-4-methanesulfinylbutanoic acidaverage_mass165.211mono_mass165.045963913smilesCS(=O)CCC(N)C(O)=OformulaC5H11NO3SinchiInChI=1S/C5H11NO3S/c1-10(9)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)inchikeyQEFRNWWLZKMPFJ-UHFFFAOYSA-Npolar_surface_area80.39refractivity39.34polarizability15.98rotatable_bond_count4acceptor_count4donor_count2physiological_charge0formal_charge0Specdb::CMs102749Specdb::CMs102750Specdb::CMs102751Specdb::CMs102752Specdb::CMs102753Specdb::CMs102754Specdb::CMs102755Specdb::CMs102756Specdb::CMs131350Specdb::CMs139084Specdb::NmrOneD5212Specdb::NmrOneD5213Specdb::NmrOneD5214Specdb::NmrOneD10002Specdb::NmrOneD10003Specdb::NmrOneD10004Specdb::NmrOneD10005Specdb::NmrOneD10006Specdb::NmrOneD10007Specdb::NmrOneD10008Specdb::NmrOneD10009Specdb::NmrOneD10010Specdb::NmrOneD10011Specdb::NmrOneD10012Specdb::NmrOneD10013Specdb::NmrOneD10014Specdb::NmrOneD10015Specdb::NmrOneD10016Specdb::NmrOneD10017Specdb::NmrOneD10018Specdb::NmrOneD10019Specdb::NmrOneD10020Specdb::NmrOneD10021Specdb::MsMs1448443Specdb::MsMs1448444Specdb::MsMs1448445Specdb::MsMs2256718Specdb::MsMs2257857Specdb::MsMs2414998Specdb::MsMs2414999Specdb::MsMs2415000Specdb::MsMs2546901Specdb::MsMs2546902Specdb::MsMs2546903Specdb::NmrTwoD2042HMDB02005824C02989CPD0-1959Keseler, I. 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Anal Biochem. 2003 Feb 1;313(1):28-33.12576054http://hmdb.ca/system/metabolites/msds/000/001/588/original/HMDB02005.pdf?1358463056Peptide methionine sulfoxide reductase msrAP0A744MSRA_ECOLImsrAhttp://ecmdb.ca/proteins/P0A744.xmlPeptide methionine sulfoxide reductase msrBP0A746MSRB_ECOLImsrBhttp://ecmdb.ca/proteins/P0A746.xmlThioredoxin-2P0AGG4THIO2_ECOLItrxChttp://ecmdb.ca/proteins/P0AGG4.xmlBiotin sulfoxide reductaseP20099BISC_ECOLIbisChttp://ecmdb.ca/proteins/P20099.xmlThioredoxin-1P0AA25THIO_ECOLItrxAhttp://ecmdb.ca/proteins/P0AA25.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlMethionine sulfoxide + Reduced Thioredoxin > Water + L-Methionine + Oxidized ThioredoxinHydrogen peroxide + L-Methionine > Water + Methionine sulfoxideLuria-Bertani (LB) mediaShake flask6.84uMtrue0.5737 oCBL21 DE3Stationary phase cultures (overnight culture)273732274Lin, 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