Kethoxal Explained

Kethoxal (3-ethoxy-1,1-dihydroxy-2-butanone) is an organic compound that has antiviral and anaplasmosis properties.^{[1] [2]} It also forms a stable covalent adduct with guanine, which makes it useful for nucleic acid structure determination.^[3]

Nucleic acid binding

Kethoxal, as with other 1,2-dicarbonyl compounds,^[4] reacts with nucleic acids. It has high specificity for guanine over other ribonucleotides. In whole RNA, it reacts preferentially with guanine residues that are not involved in hydrogen-bonding.^{[5] [6]} It can thus be used to probe the interactions involved with the secondary structure and other binding interactions of RNA^[7] and help with nucleic acid sequence analysis. The binding is reversible, which allows the kethoxal to be removed and the original RNA recovered.

Notes and References

1. Book: The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . J. Elks . Springer . 2014 . 510 . 9781475720853 .
2. Web site: Kethoxal . Merriam-Webster.
3. 10.1021/bi00829a034 . 5777326 . Reaction of guanine with glyoxal, pyruvaldehyde, and kethoxal, and the structure of the acylguanines. Synthesis of N2-alkylguanines . Robert Shapiro . Bertram I. Cohen . Shian-Jan Shiuey . Hans Maurer . Biochemistry . 1969 . 8 . 1 . 238–245.
4. The Reaction of Guanine Derivatives with 1,2-Dicarbonyl Compounds . Robert . Shapiro . John . Hachmann . Biochemistry . 1966 . 5 . 9 . 2799–2807 . 10.1021/bi00873a004 . 5961865 .
5. Kethoxal—A Potentially Useful Reagent for the Determination of Nucleotide Sequences in Single-Stranded Regions of Transfer Ribonucleic Acid . Michael . Litt . Virginia . Hancock . Biochemistry . 1967 . 6 . 6 . 1848–1854 . 10.1021/bi00858a036 . 6035923 .
6. Staehelin . Matthys . 1959 . Biochim. Biophys. Acta . 31 . 2 . 448–454 . Inactivation of virus nucleic acid with glyoxal derivatives . 10.1016/0006-3002(59)90019-8. 13628672 .
7. Gopinath . S.C.B. . Mapping of RNA-protein interactions . Analytica Chimica Acta . 636 . 117–128 . 2009 . 10.1016/j.aca.2009.01.052 . 19264161 . 2 .