Kethoxal

Kethoxal
Names
IUPAC name
3-Ethoxy-1,1-dihydroxy-2-butanone
Other names
3-Ethoxy-2-oxobutyraldehyde hydrate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.215.334 Edit this at Wikidata
KEGG
MeSH C005135
UNII
  • 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

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

  1. ^ a b c J. Elks (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 510. ISBN 9781475720853.
  2. ^ SciFinder record for CASRN 27762-78-3
  3. ^ "Kethoxal". Merriam-Webster.
  4. ^ 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.
  5. ^ 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.
  6. ^ 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.
  7. ^ 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.
  8. ^ Gopinath, S.C.B. (2009). "Mapping of RNA-protein interactions". Analytica Chimica Acta. 636 (2): 117–128. Bibcode:2009AcAC..636..117G. doi:10.1016/j.aca.2009.01.052. PMID 19264161.

Content Disclaimer

Informasi ini disarikan dari Wikipedia dan disajikan kembali untuk tujuan edukasi. Konten tersedia di bawah lisensi CC BY-SA 3.0. Kami tidak bertanggung jawab atas ketidakakuratan data yang bersumber dari kontribusi publik tersebut.

  1. The information displayed on this website is sourced in part or in whole from Wikipedia and has been adapted for the purpose of restating it. We strive to provide accurate and relevant information, however:
  2. There is no guarantee of absolute accuracy. Wikipedia is an open, collaborative project that can be edited by anyone, so information is subject to change.
  3. It is not intended to constitute professional advice. The content displayed is for informational and educational purposes only. For important decisions (e.g., medical, legal, or financial), please consult a professional.
  4. Content copyright. Wikipedia is licensed under the Creative Commons Attribution-ShareAlike License (CC BY-SA). This means that content may be reused with appropriate attribution and shared under a similar license.
  5. Responsible use. Any risk arising from the use of information from this website is entirely the responsibility of the user.