Kethoxal
Chemical compound
From Wikipedia, the free encyclopedia
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]
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| Names | |
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| IUPAC name
3-Ethoxy-1,1-dihydroxy-2-butanone | |
| Other names
3-Ethoxy-2-oxobutyraldehyde hydrate | |
| Identifiers | |
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3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.215.334 |
| KEGG | |
| MeSH | C005135 |
PubChem CID |
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| UNII |
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CompTox Dashboard (EPA) |
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| 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).
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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]