301. Formation of malonaldehyde and acetaldehyde from the oxidation of 2'-deoxyribonucleosides
- Author
-
Takashi Miyake and Takayuki Shibamoto
- Subjects
chemistry.chemical_classification ,Deoxyribonucleosides ,Chromatography, Gas ,Acetaldehyde ,General Chemistry ,Medicinal chemistry ,Aldehyde ,Nucleobase ,Deoxyribonucleoside ,chemistry.chemical_compound ,Deoxyribose ,chemistry ,Reagent ,Malondialdehyde ,Ribose ,Organic chemistry ,General Agricultural and Biological Sciences ,Oxidation-Reduction - Abstract
2‘-Deoxyribonucleosides, ribonucleosides, nucleobases, deoxyribose, and ribose were oxidized with Fenton's reagent. Malonaldehyde (MA) formed was derivatized with N-methylhydrazine to N-methylpyrazole, and acetaldehyde formed was derivatized with cysteamine to 2-methylthiazolidine. The resulting nitrogen-containing derivatives were quantitatively analyzed using gas chromatography with a nitrogen−phosphorus detector. MA and acetaldehyde were found in 2-deoxy-d-ribose and 2‘-deoxyribonucleosides but not in ribonucleosides, nucleobases, and d-ribose. Amounts of MA formed from four deoxynucleosides were in the following order: 2‘-deoxyguanosine > 2‘-deoxycytidine > 2‘-deoxyadenosine ≥ thymidine. Amounts of acetaldehyde formed from four deoxynucleosides were in the following order: 2‘-deoxycytidine > thymidine > 2‘-deoxyadenosine ≥ 2‘-deoxyguanosine. The results suggest that the formation of MA and acetaldehyde requires a deoxy group on carbon 2‘ of a ribose moiety. Keywords: Malonaldehyde; nucleosides; acet...
- Published
- 1999