Kethoxal
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| Names | |
|---|---|
| IUPAC name
3-Ethoxy-1,1-dihydroxy-2-butanone | |
| Other names
3-Ethoxy-2-oxobutyraldehyde hydrate | |
| Identifiers | |
| 3D model (JSmol) |
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| ChEBI | |
| PubChem CID |
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| Properties | |
| C6H12O4 | |
| Molar mass | 148.16 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 | |
Kethoxal (3-ethoxy-1,1-dihydroxy-2-butanone) is an organic compound that has antiviral and anaplasmodistatic properties.[1][3] It is 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 it 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 2 3 J. Elks (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 510.
- ↑ SciFinder record for CASRN 27762-78-3
- ↑ "Kethoxal". Merriam-Webster.
- ↑ 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.
- ↑ Shapiro, Robert; Hachmann, John (1966). "The Reaction of Guanine Derivatives with 1,2-Dicarbonyl Compounds". Biochemistry. 5 (9): 2799–2807. PMID 5961865. doi:10.1021/bi00873a004.
- ↑ 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. PMID 6035923. doi:10.1021/bi00858a036.
- ↑ Staehelin, Matthys (1959). "Inactivation of virus nucleic acid with glyoxal derivatives". Biochim. Biophys. Acta. 31 (2): 448–454. PMID 13628672. doi:10.1016/0006-3002(59)90019-8.
- ↑ Gopinath, S.C.B. (2009). "Mapping of RNA-protein interactions". Analytica Chimica Acta. 636 (2): 117–128. PMID 19264161. doi:10.1016/j.aca.2009.01.052.