Kethoxal

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 Edit this at Wikidata
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).

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]

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.[citation needed]

References

  1. ^ a b c 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.