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Chemical Compound Review

Kethoxal     3-ethoxy-1,1-dihydroxy-butan- 2-one

Synonyms: kethocal, KETOXAL, Ketoxalum, Chetossale, CCRIS 5167, ...
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Disease relevance of Kethoxal


High impact information on Kethoxal

  • RNase P RNA was modified with dimethylsulfate or kethoxal in the presence or absence of tRNA, and sites of modification were detected by primer extension [4].
  • The effect of protein binding on the topography of the complex is reflected in the kethoxal reactivity of the RNA moiety [5].
  • Under conditions of stoichiometric binding at 1 mM drug concentration in vitro, both drugs strongly protect 23S rRNA bases A2058 and A2451 from dimethyl sulphate and G2505 from kethoxal modification; G2061 is also weakly protected from kethoxal [6].
  • The combination of dimethylsulfate, kethoxal, and 1-cyclohexyl-3-(2-morpholinoethyl)-carbodiimide metho-p-toluene sulfonate (CMCT) offers the full range of information on base-pairing and solvent exposure concerning the four more abundant ribonucleotides [7].
  • Protection of ribosomal RNA from kethoxal in polyribosomes. Implication of specific sites in ribosome function [8].

Biological context of Kethoxal

  • Further, since the sites of kethoxal modification within the RNA sequences of intact subunits are known, the task of identifying the components of individual ribonucleoprotein complexes should be considerably simplified [9].
  • The binding site of streptomycin on the RNAs was determined via chemical probing with dimethylsulfate and kethoxal [10].
  • Mass spectrometric investigation of protein alkylation by the RNA footprinting probe kethoxal [11].

Anatomical context of Kethoxal


Associations of Kethoxal with other chemical compounds


Gene context of Kethoxal

  • Using chemical modification with CMCT, kethoxal, DMS, DEPC, and lead, we probed the structure of the IGR in short, defined transcripts and in full-length RNA3 in vitro, in yeast extracts, and in whole yeast cells [15].
  • Although some residues are found reactive toward dimethylsulphate and kethoxal in regions predicted to be unpaired by the phylogenetic secondary structure model of 4.5S RNA, generally the reactivity is low, and some residues in internal loops are not reactive at all [16].
  • Modification of amino acids and bovine pancreatic ribonuclease A by kethoxal [17].

Analytical, diagnostic and therapeutic context of Kethoxal


  1. Accessibility of guanine at position 44 in the invariant sequence 5'CCG44AAC3' of Escherichia coli 5S RNA to reaction with kethoxal. Larrinua, I., Delihas, N. Proc. Natl. Acad. Sci. U.S.A. (1979) [Pubmed]
  2. Secondary structure of the 5' end of bacteriophage MS2 RNA Methoxyamine and kethoxal modification. Iserentant, D., Fiers, W. Eur. J. Biochem. (1979) [Pubmed]
  3. Diminished virucidal activity of kethoxal against vesicular stomatitis virus pretreated with guanidinating reagent and proteases. Sabina, L.R., Morrow, D.G., Szabo, R.A. Acta Virol. (1976) [Pubmed]
  4. Phylogenetic comparative chemical footprint analysis of the interaction between ribonuclease P RNA and tRNA. LaGrandeur, T.E., Hüttenhofer, A., Noller, H.F., Pace, N.R. EMBO J. (1994) [Pubmed]
  5. The structure of the RNA binding site of ribosomal proteins S8 and S15. Müller, R., Garrett, R.A., Noller, H.F. J. Biol. Chem. (1979) [Pubmed]
  6. Interaction of the antibiotics clindamycin and lincomycin with Escherichia coli 23S ribosomal RNA. Douthwaite, S. Nucleic Acids Res. (1992) [Pubmed]
  7. Direct probing of RNA structures and RNA-protein interactions in the HIV-1 packaging signal by chemical modification and electrospray ionization fourier transform mass spectrometry. Yu, E., Fabris, D. J. Mol. Biol. (2003) [Pubmed]
  8. Protection of ribosomal RNA from kethoxal in polyribosomes. Implication of specific sites in ribosome function. Brow, D.A., Noller, H.F. J. Mol. Biol. (1983) [Pubmed]
  9. Ribonucleic acid-protein cross-linking within the intact Escherichia coli ribosome, utilizing ethylene glycol bis[3-(2-ketobutyraldehyde) ether], a reversible, bifunctional reagent: identification of 30S proteins. Brewer, L.A., Noller, H.F. Biochemistry (1983) [Pubmed]
  10. In vitro selection and characterization of streptomycin-binding RNAs: recognition discrimination between antibiotics. Wallace, S.T., Schroeder, R. RNA (1998) [Pubmed]
  11. Mass spectrometric investigation of protein alkylation by the RNA footprinting probe kethoxal. Akinsiku, O.T., Yu, E.T., Fabris, D. Journal of mass spectrometry : JMS. (2005) [Pubmed]
  12. Cytogenetic response to 1,2-dicarbonyls and hydrogen peroxide in Chinese hamster ovary AUXB1 cells and human peripheral lymphocytes. Tucker, J.D., Taylor, R.T., Christensen, M.L., Strout, C.L., Hanna, M.L., Carrano, A.V. Mutat. Res. (1989) [Pubmed]
  13. Induction of four proteins in eukaryotic cells by kethoxal bis(thiosemicarbazone). Levinson, W., Oppermann, H., Jackson, J. Biochim. Biophys. Acta (1978) [Pubmed]
  14. Nucleotide sequences of accessible regions of 23S RNA in 50S ribosomal subunits. Herr, W., Noller, H.F. Biochemistry (1978) [Pubmed]
  15. The brome mosaic virus RNA3 intergenic replication enhancer folds to mimic a tRNA TpsiC-stem loop and is modified in vivo. Baumstark, T., Ahlquist, P. RNA (2001) [Pubmed]
  16. Structure of 4.5S RNA in the signal recognition particle of Escherichia coli as studied by enzymatic and chemical probing. Lentzen, G., Moine, H., Ehresmann, C., Ehresmann, B., Wintermeyer, W. RNA (1996) [Pubmed]
  17. Modification of amino acids and bovine pancreatic ribonuclease A by kethoxal. Iijima, H., Patrzyc, H., Bello, J. Biochim. Biophys. Acta (1977) [Pubmed]
  18. Yeast precursor ribosomal RNA. Molecular cloning and probing the higher-order structure of the internal transcribed spacer I by kethoxal and dimethylsulfate modification. Thweatt, R., Lee, J.C. J. Mol. Biol. (1990) [Pubmed]
  19. Sequence determination of Gp-rich oligonucleotides by means of the Kethoxal modification. Min Jou, W., Fiers, W. FEBS Lett. (1976) [Pubmed]
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