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Chemical Compound Review

D-Cystein     (2R)-2-amino-3-sulfanyl- propanoic acid

Synonyms: D-Zystein, D-CYSH, D-cysteine, D-CYCSTEINE, H-D-CYS-OH, ...
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Disease relevance of cysteine

  • Cysteine-rich 61 (CCN1) is a matricellular protein of which expression is up-regulated in cancer and various vascular diseases [1].
  • Using a reverse genetic system based on the ARM strain of LCMV, we have previously shown that Z has a strong inhibitory activity on LCMV minigenome transcription and RNA replication (T. I. Cornu and J. C. de la Torre, J. Virol. 75:9415-9426, 2001) [2].
  • OBJECTIVE: To investigate the importance of monocyte recruitment in thrombus resolution and the role of cysteine-cysteine (CC) chemokines and the CC chemokine receptor, CCR2, in this process [3].
  • In contrast, alterations of the conserved cysteine (Cys76), basic domain (Arg87 and Lys95), and other residues (Gln65) did not impair the incorporation of Vpr into virus-like particles directed by HIV-1 Gag [4].
  • The present studies aimed to elucidate how the modulation of gamma-glutamyl transpeptidase (gammaGT) activity in human hepatoma (HepG2) cell line influences H(2)O(2) production, caspase 3 activity, protein S-thiolation by glutathione (GSH), cysteinyl-glycine (Cys-Gly) and cysteine (Cys), and the level of other redox forms of these thiols [5].

High impact information on cysteine


Biological context of cysteine

  • The NAR CDR3 Cys generally are encoded by preferred reading frames of rearranging D segments, providing a clear design for use of preferred reading frame in antigen receptor D regions [10].
  • The Arg-1 to Cys mutation led to the dimerization of protein C with another plasmatic component, as evidenced by the presence in the plasma of a high molecular weight form of protein C that disappeared after reduction [11].
  • Amino acid sequence analysis of peptides derived from the 2-azido-[32P]ATP-labeled A subunit indicates labeling of two peptides: a 12-kDa fragment which begins at residue 511 and contains Cys532 and a 3-kDa fragment which begins at residue 233 and contains the glycine-rich loop and Cys254 [12].
  • These results confirm that C1 functions in DNA binding and transcriptional activation and that hormone binding activity can be localized to the C-terminal half of the protein [13].
  • Mutation of a conserved cysteine residue (C97) that is part of an N-terminal zinc-finger motif in APO3G abolished multimerization of APO3G; however, the C97 mutation inhibited neither in vitro deaminase activity nor antiviral function of APO3G [14].

Anatomical context of cysteine

  • Further studies revealed that the conditioned medium of plasmin-treated carcinoma cells supports endothelial cell migration and that antibodies specific to CCN1 blocked this enhancing effect [1].
  • Glycosylphosphatidylinositol-anchored ectodomain receptors showed good cell surface expression in CHO cells, but only S281HCS was able to bind TSH specifically, illustrating the importance of C283, or the putative disulphide bond, in maintaining the conformation of the ligand binding site [15].
  • We assume that Asc and GSH were located mainly in the epithelium, UA mainly in the extracellular space and Cys in both spaces [16].
  • We suggest that neither C-terminal Cys-rich nor Pro-X domains are essential for gamma-zein retention in oocyte vesicles [17].
  • Utilizing the antibodies specific for the cys-rich domain of the type IIA procollagen N-propeptide, we localized type IIA procollagen in the pericellular and interterritorial matrix of condensing pre-chondrogenic mesenchyme (day 5) and early cartilage (days 7-9) [18].

Associations of cysteine with other chemical compounds


Gene context of cysteine

  • Identification of a novel integrin alpha 6 beta 1 binding site in the angiogenic inducer CCN1 (CYR61) [24].
  • Deletion of CCR2 or blockade of all CC chemokines inhibited both monocyte recruitment (P < .05) and thrombus resolution (P < .01), but knocking out MCP-1 had no effect [3].
  • The interaction of V and DDB1 involves the carboxyl-terminal domain of V in that either deletion of the V carboxyl-terminal domain or substitution of the cysteine residues (C189, C193, C205, C207, C210, C214, and C217) in the zinc-binding domain with alanine was able to disrupt binding to DDB1 [25].
  • In human umbilical vascular endothelial cells (HUVECs), VWC, TSP and CT modules, as well as a full-length CCN2, were capable of efficiently activating the ERK signal transduction cascade, whereas IGFBP was not [26].
  • Mutation of the conserved N-terminal cysteine (Cys92) of human presenilin 1 causes increased A beta42 secretion in mammalian cells but impaired Notch/lin-12 signalling in C. elegans [27].

Analytical, diagnostic and therapeutic context of cysteine

  • Sequence analysis and modeling show that there are only two types of expressed NAR genes, each having different combinations of noncanonical cysteine (Cys) residues in the V domains that likely form disulfide bonds to stabilize the single antigen-recognition unit [10].
  • To determine the roles of individual cysteines in GABP redox regulation, we generated a series of serine substitution mutants by site-directed mutagenesis and identified three redox-sensitive cysteine residues in GABPalpha (Cys388, Cys401, and Cys421) [28].
  • The absorption spectrum, heme fluorescence quenching, and heme titration analysis of the wild-type protein versus those of purified double cysteine mutant (Cys264/Cys281 --> Ala/Ala) suggest a role of the HRMs in heme binding [29].
  • Assembly of single-chain peptides from three different segments was achieved by the tandem Cys/OPro ligation to form two amide bonds, an Xaa-Cys and then an Xaa-OPro [30].
  • In contrast to the destabilizing effect of Cys substitution at the core heptad a or d positions of model peptides C30a and C33d, circular dichroism spectroscopy showed that Cys substitutions at the heptad g positions of the ProP peptide had little or no effect on coiled-coil stability [31].


  1. Proteolysis of CCN1 by plasmin: functional implications. Pendurthi, U.R., Tran, T.T., Post, M., Rao, L.V. Cancer Res. (2005) [Pubmed]
  2. Characterization of the arenavirus RING finger Z protein regions required for Z-mediated inhibition of viral RNA synthesis. Cornu, T.I., de la Torre, J.C. J. Virol. (2002) [Pubmed]
  3. Monocyte recruitment in venous thrombus resolution. Ali, T., Humphries, J., Burnand, K., Sawyer, B., Bursill, C., Channon, K., Greaves, D., Rollins, B., Charo, I.F., Smith, A. J. Vasc. Surg. (2006) [Pubmed]
  4. Identification of residues in the N-terminal acidic domain of HIV-1 Vpr essential for virion incorporation. Mahalingam, S., Khan, S.A., Jabbar, M.A., Monken, C.E., Collman, R.G., Srinivasan, A. Virology (1995) [Pubmed]
  5. The effects of modulation of gamma-glutamyl transpeptidase activity in HepG2 cells on thiol homeostasis and caspase-3-activity. Iciek, M., Chwatko, G., Rokita, H., Bald, E., Włodek, L. Biochim. Biophys. Acta (2007) [Pubmed]
  6. Evidence of oxidant-induced injury to epithelial cells during inflammatory bowel disease. McKenzie, S.J., Baker, M.S., Buffinton, G.D., Doe, W.F. J. Clin. Invest. (1996) [Pubmed]
  7. Determinants of Ca2+ permeability in both TM1 and TM2 of high affinity kainate receptor channels: diversity by RNA editing. Köhler, M., Burnashev, N., Sakmann, B., Seeburg, P.H. Neuron (1993) [Pubmed]
  8. Quality control of ER synthesized proteins: an exposed thiol group as a three-way switch mediating assembly, retention and degradation. Fra, A.M., Fagioli, C., Finazzi, D., Sitia, R., Alberini, C.M. EMBO J. (1993) [Pubmed]
  9. Identification and characterization of Ref-1, a nuclear protein that facilitates AP-1 DNA-binding activity. Xanthoudakis, S., Curran, T. EMBO J. (1992) [Pubmed]
  10. Structural analysis of the nurse shark (new) antigen receptor (NAR): molecular convergence of NAR and unusual mammalian immunoglobulins. Roux, K.H., Greenberg, A.S., Greene, L., Strelets, L., Avila, D., McKinney, E.C., Flajnik, M.F. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  11. Five novel mutations located in exons III and IX of the protein C gene in patients presenting with defective protein C anticoagulant activity. Gandrille, S., Alhenc-Gelas, M., Gaussem, P., Aillaud, M.F., Dupuy, E., Juhan-Vague, I., Aiach, M. Blood (1993) [Pubmed]
  12. Inhibition and labeling of the coated vesicle V-ATPase by 2-azido-[32P]ATP. Zhang, J., Vasilyeva, E., Feng, Y., Forgac, M. J. Biol. Chem. (1995) [Pubmed]
  13. Structure-function properties of the chicken progesterone receptor A synthesized from complementary deoxyribonucleic acid. Carson, M.A., Tsai, M.J., Conneely, O.M., Maxwell, B.L., Clark, J.H., Dobson, A.D., Elbrecht, A., Toft, D.O., Schrader, W.T., O'Malley, B.W. Mol. Endocrinol. (1987) [Pubmed]
  14. Monomeric APOBEC3G Is Catalytically Active and Has Antiviral Activity. Opi, S., Takeuchi, H., Kao, S., Khan, M.A., Miyagi, E., Goila-Gaur, R., Iwatani, Y., Levin, J.G., Strebel, K. J. Virol. (2006) [Pubmed]
  15. Effects of mutations involving the highly conserved S281HCC motif in the extracellular domain of the thyrotropin (TSH) receptor on TSH binding and constitutive activity. Ho, S.C., Van Sande, J., Lefort, A., Vassart, G., Costagliola, S. Endocrinology (2001) [Pubmed]
  16. Quantitative determination of water-soluble scavengers in neoplastic and non-neoplastic human breast tissue. Honegger, C.G., Torhorst, J., Langemann, H., Kabiersch, A., Krenger, W. Int. J. Cancer (1988) [Pubmed]
  17. Role of structural domains for maize gamma-zein retention in Xenopus oocytes. Torrent, M., Geli, M.I., Ruiz-Avila, L., Canals, J.M., Puigdomènech, P., Ludevid, D. Planta (1994) [Pubmed]
  18. Type IIA procollagen: expression in developing chicken limb cartilage and human osteoarthritic articular cartilage. Nah, H.D., Swoboda, B., Birk, D.E., Kirsch, T. Dev. Dyn. (2001) [Pubmed]
  19. Genetic evidence for in vivo cross-specificity of the CaaX-box protein prenyltransferases farnesyltransferase and geranylgeranyltransferase-I in Saccharomyces cerevisiae. Trueblood, C.E., Ohya, Y., Rine, J. Mol. Cell. Biol. (1993) [Pubmed]
  20. Structure-function studies of human arylamine N-acetyltransferases NAT1 and NAT2. Functional analysis of recombinant NAT1/NAT2 chimeras expressed in Escherichia coli. Dupret, J.M., Goodfellow, G.H., Janezic, S.A., Grant, D.M. J. Biol. Chem. (1994) [Pubmed]
  21. Identification of active-site residues in protease 3C of hepatitis A virus by site-directed mutagenesis. Gosert, R., Dollenmaier, G., Weitz, M. J. Virol. (1997) [Pubmed]
  22. Factors Affecting S-Homocysteinylation of LDL Apoprotein B. Zinellu, A., Zinellu, E., Sotgia, S., Formato, M., Cherchi, G.M., Deiana, L., Carru, C. Clin. Chem. (2006) [Pubmed]
  23. The Roles of Three Palmitoylation Sites of RPE65 in Its Membrane Association and Isomerohydrolase Activity. Takahashi, Y., Moiseyev, G., Chen, Y., Ma, J.X. Invest. Ophthalmol. Vis. Sci. (2006) [Pubmed]
  24. Identification of a novel integrin alpha 6 beta 1 binding site in the angiogenic inducer CCN1 (CYR61). Leu, S.J., Liu, Y., Chen, N., Chen, C.C., Lam, S.C., Lau, L.F. J. Biol. Chem. (2003) [Pubmed]
  25. The V protein of the paramyxovirus SV5 interacts with damage-specific DNA binding protein. Lin, G.Y., Paterson, R.G., Richardson, C.D., Lamb, R.A. Virology (1998) [Pubmed]
  26. Multiple activation of mitogen-activated protein kinases by purified independent CCN2 modules in vascular endothelial cells and chondrocytes in culture. Kubota, S., Kawaki, H., Kondo, S., Yosimichi, G., Minato, M., Nishida, T., Hanagata, H., Miyauchi, A., Takigawa, M. Biochimie (2006) [Pubmed]
  27. Mutation of the conserved N-terminal cysteine (Cys92) of human presenilin 1 causes increased A beta42 secretion in mammalian cells but impaired Notch/lin-12 signalling in C. elegans. Zhang, D.M., Levitan, D., Yu, G., Nishimura, M., Chen, F., Tandon, A., Kawarai, T., Arawaka, S., Supala, A., Song, Y.Q., Rogaeva, E., Liang, Y., Holmes, E., Milman, P., Sato, C., Zhang, L., St George-Hyslop, P. Neuroreport (2000) [Pubmed]
  28. Identification of redox-sensitive cysteines in GA-binding protein-alpha that regulate DNA binding and heterodimerization. Chinenov, Y., Schmidt, T., Yang, X.Y., Martin, M.E. J. Biol. Chem. (1998) [Pubmed]
  29. Heme oxygenase-2 is a hemoprotein and binds heme through heme regulatory motifs that are not involved in heme catalysis. McCoubrey, W.K., Huang, T.J., Maines, M.D. J. Biol. Chem. (1997) [Pubmed]
  30. Tandem ligation of multipartite peptides with cell-permeable activity. Eom, K.D., Miao, Z., Yang, J.L., Tam, J.P. J. Am. Chem. Soc. (2003) [Pubmed]
  31. Detection of alpha-helical coiled-coil dimer formation by spin-labeled synthetic peptides: a model parallel coiled-coil peptide and the antiparallel coiled coil formed by a replica of the ProP C-terminus. Hillar, A., Tripet, B., Zoetewey, D., Wood, J.M., Hodges, R.S., Boggs, J.M. Biochemistry (2003) [Pubmed]
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