Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 10:23:28 -0600 |
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Update Date | 2015-09-13 12:56:06 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | L-Cystine |
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Description | 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. |
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Structure | |
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Synonyms: | - (-)-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
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Chemical Formula: | C6H12N2O4S2 |
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Weight: | Average: 240.3 Monoisotopic: 240.023848262 |
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InChI Key: | LEVWYRKDKASIDU-IMJSIDKUSA-N |
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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 |
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CAS number: | 56-89-3 |
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IUPAC Name: | (2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}propanoic acid |
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Traditional IUPAC Name: | L-cystine |
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SMILES: | N[C@@H](CSSC[C@H](N)C(O)=O)C(O)=O |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | L-cysteine-S-conjugates |
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Alternative Parents | |
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Substituents | - L-cysteine-s-conjugate
- Alpha-amino acid
- L-alpha-amino acid
- Dicarboxylic acid or derivatives
- Organic disulfide
- Dialkyldisulfide
- Amino acid
- Sulfenyl compound
- Carboxylic acid
- Organopnictogen compound
- Organic nitrogen compound
- Primary amine
- Organosulfur compound
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Organic oxygen compound
- Carbonyl group
- Hydrocarbon derivative
- Amine
- Organic oxide
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Physical Properties |
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State: | Solid |
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Charge: | 0 |
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Melting point: | 260.5 °C |
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Experimental Properties: | Property | Value | Source |
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Water Solubility: | 0.19 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)] | PhysProp | LogP: | -5.08 [CHMELIK,J ET AL. (1991)] | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Cytoplasm |
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Reactions: | |
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SMPDB Pathways: | Not Available |
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KEGG Pathways: | |
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EcoCyc Pathways: | Not Available |
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Concentrations |
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| Not Available |
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Spectra |
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Spectra: | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS) | splash10-00kb-0950000000-a803bc05843192dd737d | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-00kb-0940000000-f82b905ef9e7c9e47552 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS) | splash10-00di-9850000000-49b9a52a8387d6d6f272 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (4 TMS) | splash10-014j-1970000000-9576699202733d4fd7ed | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00kb-0950000000-a803bc05843192dd737d | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00di-9850000000-49b9a52a8387d6d6f272 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-014j-1970000000-9576699202733d4fd7ed | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00kb-0930000000-7cb336c3f272fd0fcd6b | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00kb-0920000000-1c414573da4bbe4a66dd | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0076-9400000000-211575093fd775db5d54 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-0076-9112000000-ee49e3b674a4f8bb9ecd | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_2_5) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0006-0890000000-51a32ee40240e45646bc | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-00di-9700000000-4054924ddfb90f120e67 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-00di-9100000000-085d45702e61de0f8e4d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-00di-9710000000-9321541af2ad89bd0478 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 1V, negative | splash10-000i-0090000000-041bfa55cb183f42f454 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 1V, negative | splash10-000i-0190000000-3611e8b6715129842130 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 2V, negative | splash10-000i-0190000000-dbafdd64edad14af9281 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 2V, negative | splash10-000i-0290000000-6b80d283287249ba4b87 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 3V, negative | splash10-000i-0390000000-c091ce388dfcbd339e3f | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 3V, negative | splash10-0079-0690000000-c808ac294a0bc182c5eb | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 4V, negative | splash10-0079-0970000000-36297b29c4ef45c658e3 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 4V, negative | splash10-00dr-0940000000-a8c735a0f9082cfd7c7c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 5V, negative | splash10-00di-1920000000-9d55705325536cca5eb2 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 5V, negative | splash10-00di-1910000000-cd18de2585913152e907 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 6V, negative | splash10-00di-1900000000-3118609f8682bee472c6 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 7V, negative | splash10-00di-2900000000-213ccc3c067486ff9444 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 8V, negative | splash10-00di-3900000000-df68db23afd937a9a75d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 9V, negative | splash10-00di-4900000000-b46d26f57a194d2ff648 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 10V, negative | splash10-00di-6900000000-5535cccb24de733cada3 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-006w-2970000000-b80e0aef184b74ce7a36 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00re-4910000000-a09277c5a6bfc432eb79 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00xu-9600000000-0518bfcaab380952c123 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-3590000000-aa667d3c092c5af3ae7f | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00xr-5910000000-122bd251359ca80b184c | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00dr-9300000000-bbb14e684ff7c06e7916 | View in MoNA |
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MS | Mass Spectrum (Electron Ionization) | splash10-000x-9000000000-ae0f516d71e6a49fe52f | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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References |
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References: | - Alexander S, Ison C: Evaluation of commercial kits for the identification of Neisseria gonorrhoeae. J Med Microbiol. 2005 Sep;54(Pt 9):827-31. Pubmed: 16091433
- 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. Pubmed: 12520765
- Behr T, Becker W, Hannappel E, Goldenberg DM, Wolf F: Targeting of liver metastases of colorectal cancer with IgG, F(ab')2, and Fab' anti-carcinoembryonic antigen antibodies labeled with 99mTc: the role of metabolism and kinetics. Cancer Res. 1995 Dec 1;55(23 Suppl):5777s-5785s. Pubmed: 7493346
- Coe FL, Evan A, Worcester E: Kidney stone disease. J Clin Invest. 2005 Oct;115(10):2598-608. Pubmed: 16200192
- Engelborghs S, Marescau B, De Deyn PP: Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Neurochem Res. 2003 Aug;28(8):1145-50. Pubmed: 12834252
- Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
- 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. Pubmed: 21097882
- Kubilus J, MacDonald MJ, Baden HP: Epidermal proteins of cultured human and bovine keratinocytes. Biochim Biophys Acta. 1979 Jun 19;578(2):484-92. Pubmed: 486533
- Mitchell BF, Chibbar R: Synthesis and metabolism of oxytocin in late gestation in human decidua. Adv Exp Med Biol. 1995;395:365-80. Pubmed: 8713992
- Mogil'naia GM, Shubich MG: [Comparison of the histochemical bases of epidermis differentiation in vertebrates] Arkh Anat Gistol Embriol. 1976 Mar;70(3):46-52. Pubmed: 1275714
- Orakzai N, Hanbury DC, Farrington K: Screening for biochemical abnormalities in urolithiasis patients. J Ayub Med Coll Abbottabad. 2004 Apr-Jun;16(2):60-3. Pubmed: 15455621
- Park M, Helip-Wooley A, Thoene J: Lysosomal cystine storage augments apoptosis in cultured human fibroblasts and renal tubular epithelial cells. J Am Soc Nephrol. 2002 Dec;13(12):2878-87. Pubmed: 12444206
- Peters T, Thaete C, Wolf S, Popp A, Sedlmeier R, Grosse J, Nehls MC, Russ A, Schlueter V: A mouse model for cystinuria type I. Hum Mol Genet. 2003 Sep 1;12(17):2109-20. Pubmed: 12923163
- Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. Pubmed: 14992292
- Rossi S, Herrine SK, Navarro VJ: Cystinosis as a cause of noncirrhotic portal hypertension. Dig Dis Sci. 2005 Jul;50(7):1372-5. Pubmed: 16047489
- Rumpold H, Mascher K, Untergasser G, Plas E, Hermann M, Berger P: Trans-differentiation of prostatic stromal cells leads to decreased glycoprotein hormone alpha production. J Clin Endocrinol Metab. 2002 Nov;87(11):5297-303. Pubmed: 12414905
- Sakhaee K: Pathogenesis and medical management of cystinuria. Semin Nephrol. 1996 Sep;16(5):435-47. Pubmed: 8890399
- Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. Pubmed: 2026685
- Sonies BC, Almajid P, Kleta R, Bernardini I, Gahl WA: Swallowing dysfunction in 101 patients with nephropathic cystinosis: benefit of long-term cysteamine therapy. Medicine (Baltimore). 2005 May;84(3):137-46. Pubmed: 15879904
- Terada T, Maeda H, Okamoto K, Nishinaka T, Mizoguchi T, Nishihara T: Modulation of glutathione S-transferase activity by a thiol/disulfide exchange reaction and involvement of thioltransferase. Arch Biochem Biophys. 1993 Jan;300(1):495-500. Pubmed: 8424686
- Tezuka T, Takahashi M: The cystine-rich envelope protein from human epidermal stratum corneum cells. J Invest Dermatol. 1987 Jan;88(1):47-51. Pubmed: 3794387
- 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. Pubmed: 18331064
- Worcester EM, Coe FL, Evan AP, Parks JH: Reduced renal function and benefits of treatment in cystinuria vs other forms of nephrolithiasis. BJU Int. 2006 Jun;97(6):1285-90. Pubmed: 16686727
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Synthesis Reference: | 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. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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Links |
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External Links: | |
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