I know, for instance, that RNA is much more succetible to alkaline hydrolysis than DNA and this difference is determined by the presence of 2'-hydroxyl group in ribose. I have also heard that "DNA is more stable" and thus was selected as the repository of genetic information. Though, I still haven't understood why the lack of just one hydroxyl would lead to more stability...

  • $\begingroup$ @Chris ok, I will actually delete the other because something similar has already been asked $\endgroup$
    – El Cid
    Commented Feb 24, 2015 at 21:35
  • $\begingroup$ My answer to this question may interest you, specifically the part about sugar pucker: biology.stackexchange.com/questions/19115/… $\endgroup$
    – canadianer
    Commented Feb 24, 2015 at 23:12
  • $\begingroup$ From a chemical point of view, the phosphate can form a bond with the 2' hydroxyl, forming a cyclic structure and breaking the bond with the next nucleotide, thus breaking the RNA backbone. $\endgroup$
    – user137
    Commented Feb 25, 2015 at 3:07

1 Answer 1


As user137 said, the general base abstracts a proton from the 2'OH and subsequently the 2'O- renders a nucleophilic attack on the δ+ Phosphorous, leading to the hydrolysis of the phosphodiester bond. There can be slight variations in the mechanism and the intermediates; for details see this review.

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After hydrolysis both 2'- and 3'- phosphates can form.

RNA is not thermodynamically unstable; apart from being unstable in the presence of a strong base RNA is biochemically unstable too. This is because there are several RNAses and most of them degrade RNA by a mechanism similar to alkaline hydrolysis (they cannot act on DNA). Also see this post.


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