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Chemical Compound Review

Mecisteina     methyl(2S)-2-amino-3- sulfanyl-propanoate

Synonyms: mecysteine, Mecysteinum, AG-K-62525, CHEBI:41531, AC1L1GUG, ...
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High impact information on Acthiol J

  • Our data unambiguously demonstrate that YopT cleaves N-terminal to the prenylated cysteine in RhoA, Rac, and Cdc42 and that the cleavage product of the GTPases is geranylgeranyl cysteine methyl ester [1].
  • Next, we produced a specific polyclonal antibody against farnesyl cysteine methyl ester allowing prenylation analysis avoiding the metabolic labeling restrictions [2].
  • Two models have been proposed for the selective targeting of K-Ras4B, which contains a C-terminal farnesyl cysteine methyl ester adjacent to a polybasic peptide segment, to the cytosolic face of the plasma membrane [3].
  • Endoproteolytic cleavage requires the S-prenylated cysteine methyl ester and, in agreement with transfection studies, is more active with the farnesylated than geranylgeranylated cysteinyl substrate [4].
  • Prior studies of overexpressed wild-type and mutant lamin A proteins in cultured cells have indicated that the precursor possesses the typical carboxyl-terminal S-farnesylated, cysteine methyl ester and that farnesylation is required for endoproteolysis to occur [4].

Biological context of Acthiol J


Anatomical context of Acthiol J


Associations of Acthiol J with other chemical compounds


  1. Biochemical characterization of the Yersinia YopT protease: cleavage site and recognition elements in Rho GTPases. Shao, F., Vacratsis, P.O., Bao, Z., Bowers, K.E., Fierke, C.A., Dixon, J.E. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  2. RhoB prenylation is driven by the three carboxyl-terminal amino acids of the protein: evidenced in vivo by an anti-farnesyl cysteine antibody. Baron, R., Fourcade, E., Lajoie-Mazenc, I., Allal, C., Couderc, B., Barbaras, R., Favre, G., Faye, J.C., Pradines, A. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  3. A designed probe for acidic phospholipids reveals the unique enriched anionic character of the cytosolic face of the mammalian plasma membrane. Okeley, N.M., Gelb, M.H. J. Biol. Chem. (2004) [Pubmed]
  4. In vitro assay and characterization of the farnesylation-dependent prelamin A endoprotease. Kilic, F., Dalton, M.B., Burrell, S.K., Mayer, J.P., Patterson, S.D., Sinensky, M. J. Biol. Chem. (1997) [Pubmed]
  5. One-electron reduction of S-nitrosothiols in aqueous medium. Manoj, V.M., Mohan, H., Aravind, U.K., Aravindakumar, C.T. Free Radic. Biol. Med. (2006) [Pubmed]
  6. Role of a NifS-like protein from the cyanobacterium Synechocystis PCC 6803 in the maturation of FeS proteins. Jaschkowitz, K., Seidler, A. Biochemistry (2000) [Pubmed]
  7. Kinetics and mechanistic studies of the hydrolysis of diisocyanate-derived bis-thiocarbamates of cysteine methyl ester. Chipinda, I., Stetson, S.J., Depree, G.J., Simoyi, R.H., Siegel, P.D. Chem. Res. Toxicol. (2006) [Pubmed]
  8. Free radical activity of industrial fibers: role of iron in oxidative stress and activation of transcription factors. Gilmour, P.S., Brown, D.M., Beswick, P.H., MacNee, W., Rahman, I., Donaldson, K. Environ. Health Perspect. (1997) [Pubmed]
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  10. On the occurrence of multiple isoprenylated cysteine methyl ester hydrolase activities in bovine adrenal medulla. Van Dessel, G.A., De Busser, H.M., Lagrou, A.R. Biochem. Biophys. Res. Commun. (2001) [Pubmed]
  11. Cysteine transport in melanosomes from murine melanocytes. Potterf, S.B., Virador, V., Wakamatsu, K., Furumura, M., Santis, C., Ito, S., Hearing, V.J. Pigment Cell Res. (1999) [Pubmed]
  12. Behavior of mucus glycoproteins of tracheal secretory cells following L-cysteine methyl ester treatment. Yanaura, S., Takeda, H., Misawa, M. J. Pharmacobio-dyn. (1982) [Pubmed]
  13. The use of radioactive cysteine methyl ester for labeling glycosylated molecules oxidized by periodate or neuraminidase plus galactose oxidase. Mitchell, R.N., Harrison, E.H., Bowers, W.E. Arch. Biochem. Biophys. (1984) [Pubmed]
  14. Mechanistic flexibility in the reduction of copper(II) complexes of aliphatic polyamines by mercapto amino acids. Anderson, C.H., Holwerda, R.A. J. Inorg. Biochem. (1985) [Pubmed]
  15. Catalytic effects of glutathione peroxidase mimetics on the thiol reduction of cytochrome c. Engman, L., Tunek, A., Hallberg, M., Hallberg, A. Chem. Biol. Interact. (1994) [Pubmed]
  16. The role of hydrogen bonding in the selectivity of L-cysteine methyl ester (CYSM) and L-cysteine ethyl ester (CYSE) for chloride ion. Mosier-Boss, P.A., Lieberman, S.H. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. (2005) [Pubmed]
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