title: Participation of an additional 4'-hydroxymethyl group in the cleavage and isomerization of ribonucleoside 3'-phosphodiesters.
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.
authors: Department of Chemistry, University of Turku, Vatselankatu 2, FIN-20014 Turku, Finland. tuanlo@utu.fi.
authors: Luigi
authors: L
authors: Lain
authors: Harri
authors: H
authors: Lönnberg
authors: Tuomas
authors: T
authors: Lönnberg
mesh_terms: D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D015226:Dinucleoside Phosphates / Q000138:chemical synthesis*; D004952:Esters / Q000737:chemistry*; D006860:Hydrogen Bonding; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D007700:Kinetics; D009705:Nucleosides / Q000737:chemistry; D010755:Organophosphates / Q000737:chemistry; D010753:Phosphoranes / Q000737:chemistry; D012313:RNA / Q000737:chemistry; D012263:Ribonucleosides / Q000737:chemistry; D013936:Thymidine / Q000138:chemical synthesis* / Q000737:chemistry*; D014529:Uridine / Q000737:chemistry*
chemical_list: C000599527:4'-(hydroxymethyl)uridylyl-3',5'-thymidine; D015226:Dinucleoside Phosphates; D004952:Esters; D009705:Nucleosides; D010755:Organophosphates; D010753:Phosphoranes; D012263:Ribonucleosides; D012313:RNA; D013936:Thymidine; D014529:Uridine