Kethoxal

Kethoxal (3-ethoxy-1,1-dihydroxy-2-butanone) is an organic compound that has antiviral and anaplasmosis properties.[1][3] It also forms a stable covalent adduct with guanine, which makes it useful for nucleic acid structure determination.[4]

Kethoxal
Names
IUPAC name
3-Ethoxy-1,1-dihydroxy-2-butanone
Other names
3-Ethoxy-2-oxobutyraldehyde hydrate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.215.334
KEGG
MeSH C005135
UNII
  • InChI=1S/C6H12O4/c1-3-10-4(2)5(7)6(8)9/h4,6,8-9H,3H2,1-2H3
    Key: YRCRRHNVYVFNTM-UHFFFAOYSA-N
  • CCOC(C)C(=O)C(O)O
Properties
C6H12O4
Molar mass 148.158 g·mol−1
Appearance Pale yellow syrup[1]
Boiling point 145 °C (293 °F; 418 K)[1][2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Nucleic acid binding

Kethoxal, as with other 1,2-dicarbonyl compounds,[5] 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.[6][7] It can thus be used to probe the interactions involved with the secondary structure and other binding interactions of RNA[8] and help with nucleic acid sequence analysis. The binding is reversible, which allows the kethoxal to be removed and the original RNA recovered.

References
  1. J. Elks (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 510. ISBN 9781475720853.
  2. SciFinder record for CASRN 27762-78-3
  3. "Kethoxal". Merriam-Webster.
  4. Robert Shapiro; Bertram I. Cohen; Shian-Jan Shiuey; Hans Maurer (1969). "Reaction of guanine with glyoxal, pyruvaldehyde, and kethoxal, and the structure of the acylguanines. Synthesis of N2-alkylguanines". Biochemistry. 8 (1): 238–245. doi:10.1021/bi00829a034. PMID 5777326.
  5. Shapiro, Robert; Hachmann, John (1966). "The Reaction of Guanine Derivatives with 1,2-Dicarbonyl Compounds". Biochemistry. 5 (9): 2799–2807. doi:10.1021/bi00873a004. PMID 5961865.
  6. Litt, Michael; Hancock, Virginia (1967). "Kethoxal—A Potentially Useful Reagent for the Determination of Nucleotide Sequences in Single-Stranded Regions of Transfer Ribonucleic Acid". Biochemistry. 6 (6): 1848–1854. doi:10.1021/bi00858a036. PMID 6035923.
  7. Staehelin, Matthys (1959). "Inactivation of virus nucleic acid with glyoxal derivatives". Biochim. Biophys. Acta. 31 (2): 448–454. doi:10.1016/0006-3002(59)90019-8. PMID 13628672.
  8. Gopinath, S.C.B. (2009). "Mapping of RNA-protein interactions". Analytica Chimica Acta. 636 (2): 117–128. doi:10.1016/j.aca.2009.01.052. PMID 19264161.
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