Kethoxal

Chemical Compound
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ChEMBL
Properties
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NFPA 704	[[File:|50px]]
References

Kethoxal (3-ethoxy-1,1-dihydroxy-2-butanone) is an organic compound that has antiviral and anaplasmosis properties.<ref name=Elks >{{{last}}},

 J. Elks, 
  
 The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. online version, 
  
 Springer,</ref><ref>

Kethoxal(link). {{{website}}}. Merriam-Webster.

</ref> It is also forms a stable covalent adduct with guanine, which makes it useful for nucleic acid structure determination.<ref>,

 Reaction of guanine with glyoxal, pyruvaldehyde, and kethoxal, and the structure of the acylguanines. Synthesis of N2-alkylguanines, 
 Biochemistry, 
 
 Vol. 8(Issue: 1),
 pp. 238–245,
 DOI: 10.1021/bi00829a034,</ref>

Nucleic acid binding

Kethoxal, as with other 1,2-dicarbonyl compounds,<ref>,

 The Reaction of Guanine Derivatives with 1,2-Dicarbonyl Compounds, 
 Biochemistry, 
 1966,
 Vol. 5(Issue: 9),
 pp. 2799–2807,
 DOI: 10.1021/bi00873a004,
 PMID: 5961865,</ref> reacts with nucleic acids. It has high specificity for guanine it over other ribonucleotides. In whole RNA, it reacts preferentially with guanine residues that are not involved in hydrogen-bonding.<ref>, 
 Kethoxal—A Potentially Useful Reagent for the Determination of Nucleotide Sequences in Single-Stranded Regions of Transfer Ribonucleic Acid, 
 Biochemistry, 
 1967,
 Vol. 6(Issue: 6),
 pp. 1848–1854,
 DOI: 10.1021/bi00858a036,
 PMID: 6035923,</ref><ref>Staehelin, Matthys, 
 Inactivation of virus nucleic acid with glyoxal derivatives, 
 Biochim. Biophys. Acta, 
 1959,
 Vol. 31(Issue: 2),
 pp. 448–454,
 DOI: 10.1016/0006-3002(59)90019-8,
 PMID: 13628672,</ref> It can thus be used to probe the interactions involved with the secondary structure and other binding interactions of RNA<ref>Gopinath, S.C.B., 
 Mapping of RNA-protein interactions, 
 Analytica Chimica Acta, 
 2009,
 Vol. 636(Issue: 2),
 pp. 117–128,
 DOI: 10.1016/j.aca.2009.01.052,
 PMID: 19264161,</ref> and help with nucleic acid sequence analysis. The binding is reversible, which allows the kethoxal to be removed and the original RNA recovered.

References

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  Kethoxal