Participation of an additional 4 '-hydroxymethyl group in the cleavage and isomerization of ribonucleoside 3 '-phosphodiesters
: Lain L, Lonnberg H, Lonnberg T
Publisher: Royal Soc Chemistry
: 2015
: Organic and Biomolecular Chemistry
: ORGANIC & BIOMOLECULAR CHEMISTRY
: Org Biomol Chem
: 13
: 16
: 4737
: 4742
: 6
: 1477-0520
DOI: https://doi.org/10.1039/c5ob00400d(external)
4'-(Hydroxymethyl) uridylyl-3',5'-thymidine, an RNA model bearing an extra hydroxymethyl group at the 4'-position of the 3'-linked nucleoside, has been prepared and its cleavage and isomerization reactions studied over a wide pH range (from 0 to 12). Overall, the pH-rate profiles of these reactions were very similar to those of uridylyl-3',5'-uridine (UpU) - only a very modest acceleration was observed under acidic and neutral conditions. Evidently, hydrogen bond assistance by the additional hydroxymethyl function does not play a significant role.