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Chemical Compound Review

Bromoethanol     2-bromoethanol

Synonyms: AGN-PC-0DA0JR, CHEMBL468583, NSC-2869, CCRIS 3862, B65586_ALDRICH, ...
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Disease relevance of 4-01-00-01385 (Beilstein Handbook Reference)


High impact information on 4-01-00-01385 (Beilstein Handbook Reference)

  • At pH 5 in the presence of bromide, 2-bromoethanol is a major product and deuterium labeling shows that the hydroxyl is predominantly on the carbon which bore the chlorine in BCNU [2].
  • Some of these, including bromoethanol and sodium dodecyl sulfate, had little effect on the crystals below critical concentrations at which there was a sharp volume increase and loss of x-ray pattern, which could, however, be regenerated to about 3.2-A resolution [3].
  • Inhibition of methylreductase by BES and 3-bromopropionate was competitive with methylcoenzyme M, but inhibition by 2-bromoethanol exhibited mixed kinetics [4].
  • SDS-PAGE, however, showed that this enzyme amounted to more than 50% of the total cellular protein in extracts of the mutant from 2-bromoethanol-grown cells, which was fourfold higher than in extracts of the wild-type strain grown on 2-chloroethanol [5].
  • Yeast alcohol dehydrogenase was inactivated by the bromohexyl analog by an active-site-directed mechanism, with a Ki = 1.5 mM and a pseudo-bimolecular rate constant of 0.03 M-1 S-1, which is 150 times larger than the bimolecular rate constant for inactivation by 2-bromoethanol [6].

Biological context of 4-01-00-01385 (Beilstein Handbook Reference)


Anatomical context of 4-01-00-01385 (Beilstein Handbook Reference)


Associations of 4-01-00-01385 (Beilstein Handbook Reference) with other chemical compounds


Gene context of 4-01-00-01385 (Beilstein Handbook Reference)

  • Structural analysis of denaturant-protein interactions: comparison between the effects of bromoethanol and SDS on denaturation and renaturation of triclinic lysozyme [9].


  1. The involvement of cytochrome P4502E1 in 2-bromoethanol-induced hepatocyte cytotoxicity. Khan, S., Sood, C., O'Brien, P.J. Pharmacol. Toxicol. (1996) [Pubmed]
  2. Chemistry of nitrosoureas. Intermediacy of 4,5-dihydro-1,2,3-oxadiazole in 1,3-bis(2-chloroethyl)-1-nitrosourea decomposition. Brundrett, R.B. J. Med. Chem. (1980) [Pubmed]
  3. Crystallographic studies of protein denaturation and renaturation. 1. Effects of denaturants on volume and X-ray pattern of cross-linked triclinic lysozyme crystals. Yonath, A., Sielecki, A., Moult, J., Podjarny, A., Traub, W. Biochemistry (1977) [Pubmed]
  4. Reversal of 2-bromoethanesulfonate inhibition of methanogenesis in Methanosarcina sp. Smith, M.R. J. Bacteriol. (1983) [Pubmed]
  5. Adaptation of Pseudomonas sp. GJ1 to 2-bromoethanol caused by overexpression of an NAD-dependent aldehyde dehydrogenase with low affinity for halogenated aldehydes. Van der Ploeg, J.R., Kingma, J., De Vries, E.J., Van der Ven, J.G., Janssen, D.B. Arch. Microbiol. (1996) [Pubmed]
  6. omega-haloalkyl esters of 5'-adenosine monophosphate as potential active-site-directed reagents for dehydrogenases. Fries, R.W., Bohlken, D.P., Murch, B.P., Leidal, K.G., Plapp, B.V. Arch. Biochem. Biophys. (1983) [Pubmed]
  7. Synthesis from pullulan of spacer-arm, lipid, and ethyl glycosides of a tetrasaccharide [alpha-D-Glc-(1----6)-alpha-D-Glc-(1----4)-alpha-D-Glc-(1----4)-D-Glc] found in human urine; preparation of neoglycoproteins. Dahmén, J., Frejd, T., Magnusson, G., Noori, G., Carlström, A.S. Carbohydr. Res. (1984) [Pubmed]
  8. 2-(Trimethylsilyl)ethyl glycosides. Synthesis of the asialo-GM1-tetrasaccharide, spacer glycoside, and BSA and Sepharose glycoconjugates. Ray, A.K., Magnusson, G. Acta Chem. Scand. (1992) [Pubmed]
  9. Structural analysis of denaturant-protein interactions: comparison between the effects of bromoethanol and SDS on denaturation and renaturation of triclinic lysozyme. Yonath, A., Podjarny, A., Honig, B., Traub, W., Sielecki, A., Herzberg, O., Moult, J. Biophys. Struct. Mech. (1977) [Pubmed]
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