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Chemical Compound Review

Etantiolo     ethanethiol

Synonyms: Ethaanthiol, Ethanethiol, Thioethanol, Aethanethiol, Ethylmerkaptan, ...
 
 
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Disease relevance of ethanethiol

 

High impact information on ethanethiol

  • In addition, three of the four variants were shown to be phosphorylated by alkaline phosphatase digestion, microphosphate analysis, and ethanethiol derivatization coupled with amino acid sequence analysis; these variants were shown to have 1, 2, or 3 phosphate groups per peptide chain, which corresponded to their increasing acidic nature [6].
  • Measurement of oxidative DNA damage by gas chromatography-mass spectrometry: ethanethiol prevents artifactual generation of oxidized DNA bases [7].
  • Characterization of serine and threonine phosphorylation sites in beta-elimination/ethanethiol addition-modified proteins by electrospray tandem mass spectrometry and database searching [8].
  • We have determined the exact phosphorylation sites in both PHF-tau and fetal rat tau by ion-spray mass spectrometry and sequencing of ethanethiol-modified peptides [9].
  • All animals fed 3-ethylthiopropionate expired a volatile sulfur compound that was identified as ethanethiol by gas chromatography using both a general flame ionization detector and a sulfur specific flame photometric detector [10].
 

Chemical compound and disease context of ethanethiol

  • Unlike reaction of ethanethiol with 9 and 10, reaction with N-acetylecysteine or glutathione results in epoxide opening followed by dehydration leading to the formation of estradiol-4-thioethers [1].
 

Biological context of ethanethiol

 

Anatomical context of ethanethiol

 

Associations of ethanethiol with other chemical compounds

 

Gene context of ethanethiol

  • Reduction of the methyldehydroalanine (Mdha) residue of MCYST-LR with ethanethiol totally abolished the covalent binding of the toxin to PP1, but retained its inhibitory toxicity on PP1 [22].
  • In order to generalize this approach, a N(alpha)-2-phenyl ethanethiol scaffold has been developed to promote S to N acyl transfer in a manner analogous to native chemical ligation with N-terminal cysteine residues [23].
  • The fast reaction, which represents a binding reaction of ethanethiol to cytochrome c oxidase, has a k1 of 33 M-1 . s-1 and a dissociation constant Kd of 3.9 mM [24].
  • 4. Ethanethiol induces fast spectral changes in the absorption spectrum of cytochrome c, which are followed by a very slow reduction of the heme [24].
  • Moreover, an increase in pH from 3.6 to 5.1 exponentially increased the reaction rate of ethanethiol (e.g., k2 = 25-4200 L/mol/sec from pH 3.6 to 5.1) and significantly increased the reaction rate of DMDS if increased to pH 9 (k3 = 1.4 x 10(6) L2/mol2/sec) [25].
 

Analytical, diagnostic and therapeutic context of ethanethiol

  • The amino acid sequence of the purified active fraction was obtained by Edman degradation after treatment with alkaline ethanethiol [26].
  • These studies indicate that the N(alpha)-2-phenyl ethanethiol scaffold is a good candidate for the development of a ligation chemistry for the formation of Xaa-Gly peptides and other unhindered amides [23].
  • The calculated adsorption quantity of ethanethiol in MFI is close agreement with the experimental data by means of IR spectroscopy and thermogravimetry [27].
  • The self-assembly of ethanethiol (C(2)) and 1-octanethiol (C(8)) on Ag-Au(111) alloy films was studied by X-ray photoelectron spectroscopy (XPS), cyclic voltammetry (CV), and scanning tunneling microscopy (STM), to illuminate how the monolayer structures and chemisorption-induced substrate defect structures depend on the alloy composition [28].

References

  1. Reaction of thiol nucleophiles with 1,2-epoxy- and 4,5-epoxy-estrene-3-one-17 beta-ols. Ghaffari, M.A., Abul-Hajj, Y.J. J. Steroid Biochem. Mol. Biol. (1990) [Pubmed]
  2. Protection against radiation-induced mutagenesis in V79 cells by 2-[(aminopropyl)amino] ethanethiol under conditions of acute hypoxia. Grdina, D.J., Nagy, B., Hill, C.K., Sigdestad, C.P. Radiat. Res. (1989) [Pubmed]
  3. Volatile organic sulfur compounds in anaerobic sludge and sediments: biodegradation and toxicity. van Leerdam, R.C., de Bok, F.A., Lomans, B.P., Stams, A.J., Lens, P.N., Janssen, A.J. Environ. Toxicol. Chem. (2006) [Pubmed]
  4. Mercaptoethane sulphonate in cystinic calculosis therapy. Di Silverio, F., Gallucci, M., Ricciuti, G.P., Alpi, G., Fini, D., Cassanelli, A., Molinari, C. Contributions to nephrology. (1987) [Pubmed]
  5. Comparative value of different dialysis membranes, including a carbon coated membrane for removal of noxious substances in hepatic coma. Mardini, H.A., Hoenich, N., Bartlett, K., Record, C.O. The International journal of artificial organs. (1979) [Pubmed]
  6. The isolation and chemical characterization of phosphorylated enkephalin-containing peptides from bovine adrenal medulla. Watkinson, A., Young, J., Varro, A., Dockray, G.J. J. Biol. Chem. (1989) [Pubmed]
  7. Measurement of oxidative DNA damage by gas chromatography-mass spectrometry: ethanethiol prevents artifactual generation of oxidized DNA bases. Jenner, A., England, T.G., Aruoma, O.I., Halliwell, B. Biochem. J. (1998) [Pubmed]
  8. Characterization of serine and threonine phosphorylation sites in beta-elimination/ethanethiol addition-modified proteins by electrospray tandem mass spectrometry and database searching. Jaffe, H., Veeranna, n.u.l.l., Pant, H.C. Biochemistry (1998) [Pubmed]
  9. Hyperphosphorylation of tau in PHF. Morishima-Kawashima, M., Hasegawa, M., Takio, K., Suzuki, M., Yoshida, H., Watanabe, A., Titani, K., Ihara, Y. Neurobiol. Aging (1995) [Pubmed]
  10. Role of 3-ethylthiopropionate in ethionine metabolism and toxicity in rats. Steele, R.D. J. Nutr. (1982) [Pubmed]
  11. Cysteine: a potential source of error in amino acid analysis of mercaptoethane sulfonic or hydrochloric acid hydrolysates of proteins and peptides. Gardner, M.L. Anal. Biochem. (1984) [Pubmed]
  12. 2-[(Aminopropyl)amino] ethanethiol-mediated reductions in 60Co gamma-ray and fission-spectrum neutron-induced chromosome damage in V79 cells. Schwartz, J.L., Giovanazzi, S.M., Karrison, T., Jones, C., Grdina, D.J. Radiat. Res. (1988) [Pubmed]
  13. The kinetics of catalytic incineration of C2H5SH and (CH3)2S2 over a Pt/Al2O3 catalyst. Chu, H., Lee, W.T., Chiou, Y.Y., Tseng, T.K. Environmental technology. (2001) [Pubmed]
  14. Inhibition of mitochondrial electron transfer in rats by ethanethiol and methanethiol. Vahlkamp, T., Meijer, A.J., Wilms, J., Chamuleau, R.A. Clin. Sci. (1979) [Pubmed]
  15. Reconstitution of the D-glucose transporter of bovine thymocyte plasma membrane: partial purification of transport activity by chromatography on agarose lentil lectin and agarose ethanethiol. Schraw, W.P., Regen, D.M. Arch. Biochem. Biophys. (1983) [Pubmed]
  16. A selective precipitation purification procedure for multiple phosphoseryl-containing peptides and methods for their identification. Reynolds, E.C., Riley, P.F., Adamson, N.J. Anal. Biochem. (1994) [Pubmed]
  17. An improved method for the determination of gamma-carboxyglutamic acid in proteins, bone, and urine. Kuwada, M., Katayama, K. Anal. Biochem. (1983) [Pubmed]
  18. In vitro inhibition of rat liver cholest-5en-3 beta-ol (cholesterol) biosynthesis by non-mercurial sulfhydryl reagents. Abernethy, D., Hignite, C., Azarnoff, D.L. Steroids (1976) [Pubmed]
  19. HPLC-based method using sample pre-column clean-up for the determination of methanethiol and ethanethiol in parenteral amino acid solutions. do Nascimento, P.C., Bohrer, D., Rohlfes, A.L., de Carvalho, L.M., Ramirez, A. Fresenius' journal of analytical chemistry. (2001) [Pubmed]
  20. N-trichloroethoxycarbonyl-glucosamine derivatives as glycosyl donors. Dullenkopf, W., Castro-Palomino, J.C., Manzoni, L., Schmidt, R.R. Carbohydr. Res. (1996) [Pubmed]
  21. Surface-enhanced Raman spectra of VX and its hydrolysis products. Farquharson, S., Gift, A., Maksymiuk, P., Inscore, F. Applied spectroscopy. (2005) [Pubmed]
  22. Monitoring of microcystin-protein phosphatase adduct formation with immunochemical methods. Liu, B.H., Yu, F.Y., Huang, X., Chu, F.S. Toxicon (2000) [Pubmed]
  23. A new scaffold for amide ligation. Marinzi, C., Bark, S.J., Offer, J., Dawson, P.E. Bioorg. Med. Chem. (2001) [Pubmed]
  24. Reactions of mercaptans with cytochrome c oxidase and cytochrome c. Wilms, J., Lub, J., Wever, R. Biochim. Biophys. Acta (1980) [Pubmed]
  25. Effect of pH and temperature on the kinetics of odor oxidation using chlorine dioxide. Kastner, J.R., Das, K.C., Hu, C., McClendon, R. Journal of the Air & Waste Management Association (1995) (2003) [Pubmed]
  26. Purification and structure of mutacin B-Ny266: a new lantibiotic produced by Streptococcus mutans. Mota-Meira, M., Lacroix, C., LaPointe, G., Lavoie, M.C. FEBS Lett. (1997) [Pubmed]
  27. Computer simulation of the adsorption of ethanethiol in silicalite of MFI and MOR. Ju, S.G., Zeng, Y.P., Yao, H.Q. The Journal of chemical physics. (2004) [Pubmed]
  28. Self-assembly of alkanethiol monolayers on ag-au(111) alloy surfaces. Kawasaki, M., Iino, M. The journal of physical chemistry. B, Condensed matter, materials, surfaces, interfaces & biophysical. (2006) [Pubmed]
 
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