2.0 2012-05-31 10:23:28 -0600 2015-09-13 12:56:06 -0600 ECMDB00192 M2MDB000081 L-Cystine Cystine is an oxidized dimeric form of cysteine. It is formed by linking two cysteine residues via a disulfide bond (cys-S-S-cys) between the -SH groups. The L-cysteine transporter, YdeD, is required for the tolerance of E. coli cells to hydrogen peroxide. L-cystine, a product from the oxidation of L-cysteine by hydrogen peroxide, is imported back into the cytoplasm in a manner dependent on the periplasmic L-cystine-binding protein (FliY). This protein is involved in the recycling of the oxidized L-cysteine and is important for the hydrogen peroxide resistance of E. coli. In E. coli the L-cysteine/L-cystine shuttle system plays an important role in oxidative stress tolerance through providing a reducing equivalent to the periplasm in E. coli. (-)-Cystine (R-(R*,R*))-3,3'-Dithiobis 2-Amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoate 2-Amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoic acid 2-Amino-3-(2-amino-2-carboxy-ethyl)disulphanyl-propanoate 2-Amino-3-(2-amino-2-carboxy-ethyl)disulphanyl-propanoic acid 2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoate 2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoic acid 3,3'-Dithiobis 3,3'-Dithiobis-L-Alanine 3,3'-Dithiobis[2-amino-[R-(R*,R*)]-Propanoate 3,3'-Dithiobis[2-amino-[R-(R*,R*)]-Propanoic acid 3,3'-Dithiodialanine B,b'-Diamino-b,b'-dicarboxydiethyl disulfide b,B'-diamino-b,b'-dicarboxydiethyl disulphide B,b'-Dithiodialanine b,Beta'-diamino-b,b'-dicarboxydiethyl disulfide b,Beta'-diamino-b,b'-dicarboxydiethyl disulphide b,Beta'-dithiobisalanine b,Beta'-dithiodialanine Beta,beta'-Diamino-b,b'-dicarboxydiethyl disulfide Beta,beta'-Diamino-b,b'-dicarboxydiethyl disulphide Beta,beta'-Dithiobisalanine Beta,beta'-Dithiodialanine Bis(b-amino-b-carboxyethyl) disulfide Bis(b-amino-b-carboxyethyl) disulphide Bis(b-amino-beta-carboxyethyl) disulfide Bis(b-amino-beta-carboxyethyl) disulphide Bis(b-amino-β-carboxyethyl) disulfide Bis(b-amino-β-carboxyethyl) disulphide Cysteine disulfide Cysteine disulphide Cystin Cystine Cystine acid D(+)-3,3'-Dithiobis(2-aminopropanoate D(+)-3,3'-Dithiobis(2-aminopropanoate) D(+)-3,3'-Dithiobis(2-aminopropanoic acid D(+)-3,3'-Dithiobis(2-aminopropanoic acid) Dicysteine Gelucystine L-(-)-Cystine L-Cysteine disulfide L-Cysteine disulphide L-Cystin L-Cystine Oxidized L-cysteine [R-(R*,R*)]-3,3'-Dithiobis β,Beta'-diamino-b,b'-dicarboxydiethyl disulfide β,Beta'-diamino-b,b'-dicarboxydiethyl disulphide β,Beta'-dithiobisalanine β,Beta'-dithiodialanine C6H12N2O4S2 240.3 240.023848262 (2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}propanoic acid L-cystine 56-89-3 N[C@@H](CSSC[C@H](N)C(O)=O)C(O)=O InChI=1S/C6H12N2O4S2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1 LEVWYRKDKASIDU-IMJSIDKUSA-N Solid Cytoplasm Periplasm logp -3.16 ALOGPS logs -1.16 ALOGPS solubility 1.68e+01 g/l ALOGPS melting_point 260.5 oC logp -5.9 ChemAxon pka_strongest_acidic 1.56 ChemAxon pka_strongest_basic 9.34 ChemAxon iupac (2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}propanoic acid ChemAxon average_mass 240.3 ChemAxon mono_mass 240.023848262 ChemAxon smiles N[C@@H](CSSC[C@H](N)C(O)=O)C(O)=O ChemAxon formula C6H12N2O4S2 ChemAxon inchi InChI=1S/C6H12N2O4S2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1 ChemAxon inchikey LEVWYRKDKASIDU-IMJSIDKUSA-N ChemAxon polar_surface_area 126.64 ChemAxon refractivity 54.87 ChemAxon polarizability 22.77 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Cysteine and methionine metabolism ec00270 ABC transporters ec02010 Specdb::CMs 441 Specdb::CMs 442 Specdb::CMs 443 Specdb::CMs 1955 Specdb::CMs 3266 Specdb::CMs 30366 Specdb::CMs 30789 Specdb::CMs 31061 Specdb::CMs 31775 Specdb::CMs 31959 Specdb::CMs 37348 Specdb::CMs 154243 Specdb::CMs 1053872 Specdb::CMs 1053874 Specdb::CMs 1053876 Specdb::CMs 1053878 Specdb::CMs 1053879 Specdb::CMs 1053881 Specdb::CMs 1053883 Specdb::CMs 1053885 Specdb::CMs 1053887 Specdb::CMs 1053888 Specdb::CMs 1053890 Specdb::CMs 1053892 Specdb::CMs 1053894 Specdb::EiMs 1720 Specdb::NmrOneD 1167 Specdb::NmrOneD 4182 Specdb::NmrOneD 4987 Specdb::NmrOneD 4988 Specdb::NmrOneD 4989 Specdb::NmrOneD 4990 Specdb::MsMs 307 Specdb::MsMs 308 Specdb::MsMs 309 Specdb::MsMs 179796 Specdb::MsMs 179797 Specdb::MsMs 179798 Specdb::MsMs 182130 Specdb::MsMs 182131 Specdb::MsMs 182132 Specdb::MsMs 1471165 Specdb::MsMs 1471937 Specdb::MsMs 1471938 Specdb::MsMs 1471939 Specdb::MsMs 1471940 Specdb::MsMs 1471941 Specdb::MsMs 1471942 Specdb::MsMs 1471943 Specdb::MsMs 1471944 Specdb::MsMs 1471945 Specdb::MsMs 1471946 Specdb::MsMs 1471947 Specdb::MsMs 1471948 Specdb::MsMs 1471949 Specdb::MsMs 1471950 Specdb::MsMs 1471951 Specdb::NmrTwoD 991 Specdb::NmrTwoD 1197 HMDB00192 67678 60997 C00491 16283 CYSTINE Cystine Keseler, I. 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BJU Int. 2006 Jun;97(6):1285-90. 16686727 Allen JW, Shanker G, Tan KH, Aschner M: The consequences of methylmercury exposure on interactive functions between astrocytes and neurons. Neurotoxicology. 2002 Dec;23(6):755-9. 12520765 Grossi, Loris; Montevecchi, Pier Carlo. S-Nitrosocysteine and Cystine from Reaction of Cysteine with Nitrous Acid. A Kinetic Investigation. Journal of Organic Chemistry (2002), 67(24), 8625-8630. http://hmdb.ca/system/metabolites/msds/000/000/135/original/HMDB00192.pdf?1358894670 Cystathionine beta-lyase metC P06721 METC_ECOLI metC http://ecmdb.ca/proteins/P06721.xml Protein malY P23256 MALY_ECOLI malY http://ecmdb.ca/proteins/P23256.xml L-Cystine + Water <> Pyruvic acid + Ammonia + Thiocysteine R02408