DEGRADATION OF SOME PURINE AND PYRIMIDINE DERIVATIVES BY HOT ALKALI

Abstract

The effect of heating a number of purine and pyrimidine derivatives in 1 N sodium hydroxide solution at 100 °C was studied using a spectrophotometric method to determine the extent of degradation. Although adenine was stable under these conditions, adenylic acid was found to be destroyed without evidence of intermediate deamination. No other substituted purines studied were degraded. Cytidylic acid was much more readily deaminated than cytosine but in both cases destruction of the pyrimidine base occurred. Uracil and thymine were stable but uridylic acid was destroyed to the same degree as adenylic acid. The stability of uracil suggests that the destruction of cytosine occurred before deamination. The rapid deamination of cytidylic acid took place before extensive loss of base had occurred. The differences observed are related to the nature and number of substituent groups on the purine and pyrimidine ring structures.