kethoxal
{{Chembox
| ImageFile = Kethoxal.svg
| ImageSize = 200px
| ImageAlt =
| IUPACName = 3-Ethoxy-1,1-dihydroxy-2-butanone
| OtherNames = 3-Ethoxy-2-oxobutyraldehyde hydrate
| Section1 = {{Chembox Identifiers
| CASNo = 27762-78-3
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo1 = 3688-37-7
| CASNo1_Ref = {{cascite|correct|CAS}}
| CASNo1_Comment = (anhydrous)
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = E00MDP82S4
| UNII1_Ref = {{fdacite|correct|FDA}}
| UNII1 = 2HAV7G194P
| UNII1_Comment = (anhydrous)
| PubChem = 34006
| ChemSpiderID = 31346
| ChEBI = 59052
| SMILES = CCOC(C)C(=O)C(O)O
| KEGG = D04651
| InChI=1S/C6H12O4/c1-3-10-4(2)5(7)6(8)9/h4,6,8-9H,3H2,1-2H3
| InChIKey=YRCRRHNVYVFNTM-UHFFFAOYSA-N
| MeSHName = C005135
}}
| Section2 = {{Chembox Properties
| C=6|H=12|O=4
| Appearance = Pale yellow syrup
| Density =
| MeltingPt =
| BoilingPtC = 145
| BoilingPt_ref = SciFinder record for CASRN 27762-78-3
| Solubility =
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
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Kethoxal (3-ethoxy-1,1-dihydroxy-2-butanone) is an organic compound that has antiviral and anaplasmosis properties.{{Cite book | title = The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies | author = J. Elks | publisher = Springer | date = 2014 | page = 510 | url = https://books.google.com/books?id=0vXTBwAAQBAJ&dq=3-ethoxy-2-butanone&pg=PA510| isbn = 9781475720853 }}{{cite web | url = http://www.merriam-webster.com/medical/kethoxal | title = Kethoxal | publisher = Merriam-Webster}} It also forms a stable covalent adduct with guanine, which makes it useful for nucleic acid structure determination.{{cite journal | doi = 10.1021/bi00829a034 | pmid = 5777326 | title = Reaction of guanine with glyoxal, pyruvaldehyde, and kethoxal, and the structure of the acylguanines. Synthesis of N2-alkylguanines |author1=Robert Shapiro |author2=Bertram I. Cohen |author3=Shian-Jan Shiuey |author4=Hans Maurer | journal = Biochemistry | date = 1969 | volume = 8 | issue = 1 | pages = 238–245}}
Nucleic acid binding
Kethoxal, as with other 1,2-dicarbonyl compounds,{{cite journal |title= The Reaction of Guanine Derivatives with 1,2-Dicarbonyl Compounds |first1= Robert |last1= Shapiro |first2= John |last2= Hachmann |journal= Biochemistry |year= 1966 |volume= 5 |issue= 9 |pages= 2799–2807 |doi= 10.1021/bi00873a004 |pmid= 5961865 }} 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.{{cite journal |title= Kethoxal—A Potentially Useful Reagent for the Determination of Nucleotide Sequences in Single-Stranded Regions of Transfer Ribonucleic Acid |first1= Michael |last1= Litt |first2= Virginia |last2= Hancock |journal= Biochemistry |year= 1967 |volume= 6 |issue= 6 |pages= 1848–1854 |doi= 10.1021/bi00858a036 |pmid= 6035923 }}{{cite journal |last= Staehelin |first= Matthys |year= 1959 |journal= Biochim. Biophys. Acta |volume= 31 |issue= 2 |pages= 448–454 |title= Inactivation of virus nucleic acid with glyoxal derivatives |doi=10.1016/0006-3002(59)90019-8|pmid= 13628672 }} It can thus be used to probe the interactions involved with the secondary structure and other binding interactions of RNA{{cite journal| last= Gopinath |first= S.C.B. |title= Mapping of RNA-protein interactions |journal= Analytica Chimica Acta |volume= 636 |pages= 117–128 |year= 2009 |doi= 10.1016/j.aca.2009.01.052 |pmid= 19264161 |issue= 2 }} and help with nucleic acid sequence analysis. The binding is reversible, which allows the kethoxal to be removed and the original RNA recovered.{{cn|date=January 2023}}