PMID: 967670Jul 1, 1976Paper

Reactivity and selectivity in light-induced free radical reactions of 2-propanol with purine and pyrimidine mononucleotides and dinucleoside monophosphates

Nucleic Acids Research
A HavronD Elad

Abstract

Photoalkylation reactions with 2-propanol, initiated with di-tert-butyl peroxide, of a variety of purine and pyrimidine mononucleotides and dinucleoside monophosphates lead to the substitution of an alpha-hydroxyisopropyl group for the H-8 atom of adenosine and the addition of the alcohol across the 5,6-double bond of the pyrimidines. Adenosine moieties blocked at their 3'-hydroxyl group are alkylated faster than those blocked at their 5'-hydroxyl. The reactivity of the uridine moieties of 3'-UMP, 5'-UMP, and uridylyl-(3',5')-uridine is not affected by the location of the phosphate group. However, the uridine moiety of uridylyl-(3',5')-adenosine is modified faster than that of adenylyl-(3',5')-uridine. It is suggested that steric hindrance imposed by the phosphate group determines the reactivity of adenosine moieties, while base stacking involving adenosine determines the reactivity of uridine moieties. These two effects play a major role in controlling the nature and degree of the selectivity of these photoalkylation reactions for either adenosine or uridine. Cytidine has been found to be inert in these reactions.

References

Jun 4, 1974·Biochemical and Biophysical Research Communications·J Salomon, D Elad
Mar 1, 1973·Photochemistry and Photobiology·R Ben-IshaiJ Salomon
Nov 19, 1971·The Journal of Organic Chemistry·H SteinmausD Elad
Jul 29, 1970·Journal of the American Chemical Society·B Evans, R Wolfenden

Citations

Nov 1, 1979·Proceedings of the National Academy of Sciences of the United States of America·Z LivnehJ Sperling
Aug 1, 1982·Proceedings of the National Academy of Sciences of the United States of America·N J DukerD E Fishbein
May 1, 1976·Photochemistry and Photobiology·J Sperling
Aug 1, 1980·Photochemistry and Photobiology·Z LivnehJ Sperling

Related Concepts

1-Propanol
Alkylation
Photochemistry
Purine Nucleotides
Pyrimidine Nucleotides

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