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
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| Other names
3-Ethoxy-2-oxobutyraldehyde hydrate
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| 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
editKethoxal, 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
edit- ^ a b c J. Elks (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 510. ISBN 9781475720853.
- ^ 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. PMID 5777326.238-245&rft.date=1969&rft_id=info:doi/10.1021/bi00829a034&rft_id=info:pmid/5777326&rft.au=Robert Shapiro&rft.au=Bertram I. Cohen&rft.au=Shian-Jan Shiuey&rft.au=Hans Maurer&rfr_id=info:sid/en.wikipedia.org:Kethoxal" class="Z3988">
- ^ 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 5961865.2799-2807&rft.date=1966&rft_id=info:doi/10.1021/bi00873a004&rft_id=info:pmid/5961865&rft.aulast=Shapiro&rft.aufirst=Robert&rft.au=Hachmann, John&rfr_id=info:sid/en.wikipedia.org:Kethoxal" class="Z3988">
- ^ 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 6035923.1848-1854&rft.date=1967&rft_id=info:doi/10.1021/bi00858a036&rft_id=info:pmid/6035923&rft.aulast=Litt&rft.aufirst=Michael&rft.au=Hancock, Virginia&rfr_id=info:sid/en.wikipedia.org:Kethoxal" class="Z3988">
- ^ 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 13628672.448-454&rft.date=1959&rft_id=info:doi/10.1016/0006-3002(59)90019-8&rft_id=info:pmid/13628672&rft.aulast=Staehelin&rft.aufirst=Matthys&rfr_id=info:sid/en.wikipedia.org:Kethoxal" class="Z3988">
- ^ 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 19264161.117-128&rft.date=2009&rft_id=info:doi/10.1016/j.aca.2009.01.052&rft_id=info:pmid/19264161&rft.aulast=Gopinath&rft.aufirst=S.C.B.&rfr_id=info:sid/en.wikipedia.org:Kethoxal" class="Z3988">