Participation of an additional 4 '-hydroxymethyl group in the cleavage and isomerization of ribonucleoside 3 '-phosphodiesters - UTU Research Portal

A1 Refereed original research article in a scientific journal

Participation of an additional 4 '-hydroxymethyl group in the cleavage and isomerization of ribonucleoside 3 '-phosphodiesters

Authors: Lain L, Lonnberg H, Lonnberg T

Publisher: Royal Soc Chemistry

Publication year: 2015

Journal: Organic and Biomolecular Chemistry

Journal name in source: ORGANIC & BIOMOLECULAR CHEMISTRY

Journal acronym: Org Biomol Chem

Volume: 13

Issue: 16

First page : 4737

Last page: 4742

Number of pages: 6

ISSN: 1477-0520

DOI: https://doi.org/10.1039/c5ob00400d(external)

Abstract

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.