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Chemical Compound Review

Thioacetat     ethanethioate

Synonyms: Thioacetate, AC1MXGCY, CPD-435, AG-H-24930, CHEBI:30320, ...
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Disease relevance of ethanethioic acid

 

High impact information on ethanethioic acid

  • The reaction pathway of enzyme-catalyzed acetylation of the acyl-accepting sites of the yeast synthase, a Ser-OH at the acetyl transacylase site, a Cys-SH at the beta-ketoacyl synthase site, and the acyl carrier protein 4'-phosphopantetheine-SH (Pant-SH), has been investigated using the chromophoric substrate, p-nitrophenyl thioacetate [2].
  • In the reaction of 3 with thioacetate, the product underwent hydrolysis and air-oxidation to give the corresponding disulfide 6 [3].
  • The molecular structure of S-methyl thioacetate, CH3C(O)SCH3, was determined by gas electron diffraction (GED) with the assistance of quantum chemical calculations (B3LYP/6-31G and MP2/6-31G) [4].
  • The thioacetate exhibited effects similar to those seen with digitoxigenin acetate on the isolated frog and guinea pig hearts at 1 X 10(-7) dilution [5].
  • Compound 20, the thioacetate ethyl ester prodrug derivative of compound 19a, was found to be an orally active and potent inhibitor of ECE-1 activity in rats [6].
 

Associations of ethanethioic acid with other chemical compounds

 

Gene context of ethanethioic acid

  • Compound 3c, the thioacetate methyl ester derivative of compound 4c, was found to be a long acting inhibitor of ECE-1 activity in rats after oral administration [10].
  • It was shown that apart from S-methyl thioacetate (0.8 mol %), molar concentrations of other thioesters varied in a relatively narrow range from 4.2 mol % for S-methyl thiopropionate to 14.1 mol % for S-methyl thiohexanoate [11].

References

  1. Headspace gas chromatographic-mass spectrometric analysis of light hydrocarbons and volatile organosulphur compounds in reduced-pressure cultures of Clostridium. Rimbault, A., Niel, P., Darbord, J.C., Leluan, G. J. Chromatogr. (1986) [Pubmed]
  2. The yeast fatty acid synthase. Pathway for transfer of the acetyl group from coenzyme A to the Cys-SH of the condensation site. Stoops, J.K., Singh, N., Wakil, S.J. J. Biol. Chem. (1990) [Pubmed]
  3. Synthesis of potential anticancer agents. Pyrido[4,3-b][1,4]oxazines and pyrido[4,3-b][1,4]thiazines. Temple, C., Wheeler, G.P., Comber, R.N., Elliott, R.D., Montgomery, J.A. J. Med. Chem. (1983) [Pubmed]
  4. Gas electron diffraction analysis on S-methyl thioacetate, CH3C(O)SCH3. Della Védova, C.O., Romano, R.M., Oberhammer, H. J. Org. Chem. (2004) [Pubmed]
  5. Thiocardenolides II: synthesis and pharmacological evaluation of 3beta-thioacetyl-14beta-hydroxy-5beta-card-20(22)-enolide. Abramson, H.N., Huang, C.L., Ho, C.C., Walny, L.L., Hsu, Y.M. Journal of pharmaceutical sciences. (1977) [Pubmed]
  6. Synthesis and biological activity of potent heterocyclic thiol-based inhibitors of endothelin-converting enzyme-1. Firooznia, F., Gude, C., Chan, K., Tan, J., Fink, C.A., Savage, P., Beil, M.E., Bruseo, C.W., Trapani, A.J., Jeng, A.Y. Bioorg. Med. Chem. Lett. (2002) [Pubmed]
  7. Isolation of volatile sulfur-containing microbial catabolites of biotin. Westendorf, J.M., McCormick, D.B. International journal for vitamin and nutrition research. Internationale Zeitschrift für Vitamin- und Ernährungsforschung. Journal international de vitaminologie et de nutrition. (1980) [Pubmed]
  8. Lipase-assisted generation of 2-methyl-3-furanthiol and 2-furfurylthiol from thioacetates. Bel Rhlid, R., Matthey-Doret, W., Blank, I., Fay, L.B., Juillerat, M.A. J. Agric. Food Chem. (2002) [Pubmed]
  9. Identification of two rat liver proteins with paraoxonase activity: biochemical evidence for the identity of paraoxonase and arylesterase. Rodrigo, L., Gil, F., Hernández, A.F., Pla, A. Chem. Biol. Interact. (1999) [Pubmed]
  10. Design and synthesis of potent thiol-based inhibitors of endothelin converting enzyme-1. Fink, C.A., Moskal, M., Firooznia, F., Hoyer, D., Symonsbergen, D., Wei, D., Qiao, Y., Savage, P., Beil, M.E., Trapani, A.J., Jeng, A.Y. Bioorg. Med. Chem. Lett. (2000) [Pubmed]
  11. Combinatorial approach to flavor analysis. 1. Preparation and characterization of a S-methyl thioester library. Khan, J.A., Gijs, L., Berger, C., Martin, N., Piraprez, G., Spinnler, H.E., Vulfson, E.N., Collin, S. J. Agric. Food Chem. (1999) [Pubmed]
 
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