I think I read somewhere that RNA is more susceptible to high pH than DNA is. However, they are both unstable in acid. Could someone please explain why this is in terms of their chemical structure, as well as the chemical processes that occur when both are in these solutions? Any source provided would also be extremely helpful.What happens to DNA and RNA in acid and base?
Chemical Hydrolysis of DNA
At very low pH (1 or less) phosphodiester bond hydrolysis occurs accompanied by breakage of the N glycosylic bond between the base and the deoxyribose.
At very high pH, DNA is resistant to hydrolysis.
Acid hydrolysis cleaves susceptible purine N-glycosyl bonds in both DNA and RNA. When RNA is boiled in dilute acid, adenine and guanine are released, leaving an “apurinic acid” which maybe further hydrolyzed to a mixture of pyrimidine nucleotides. The pyrimidines are more resistant to acid hydrolysis. Bond cleavage of the N-glycosyl bonds requires more vigorous conditio0ns like heating with acids in an autoclave or sealed tubes. This would release cytosine and uracil. However, during the process, there is a tendency for cytosine to be deaminated to uracil. Significant hydrolysis of RNA can be obtained by treatment with 1N HCl at 100oC for 1 hour.
Base hydrolysis of RNA produces a mixture of 2’ and 3’ nucleotides of cyclic 2’, 3’-monophosphate intermediates. These are further hydrolyzed by alkali, which attacks either one of the two P-O-C linkages, to yield a mixture of 2’ and 3’ nucleoside monophosphates. DNA, on the other hand, is not readily hydrolyzed by dilute alkali because it lacks the 2’ hydroxyl group and therefore, cannot form the necessary 2’-3’ cyclic monophosphate intermediates.
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