Kethoxal

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Kethoxal
File:Kethoxal.svg
Names
IUPAC name
3-Ethoxy-1,1-dihydroxy-2-butanone
Other names
3-Ethoxy-2-oxobutyraldehyde hydrate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
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KEGG
MeSH C005135
UNII
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  • 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

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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

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  2. ^ SciFinder record for CASRN 27762-78-3
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