| Literature DB >> 24135854 |
Heidi Korhonen1, Timo Koivusalo, Suvi Toivola, Satu Mikkola.
Abstract
The transesterification of uridine 3'-phosphodiesters with a wide range of leaving group alcohols has been studied in the presence of monometallic and bimetallic complexes. The catalysis of isomerization of the phosphodiester bond was studied with a nucleoside 3'-phosphonate as a substrate. The results obtained are consistent with a step-wise mechanism, where metal ions are able to enhance both the nucleophilic attack and the departure of the leaving group. The mechanism of the catalysis depends on the acidity of the catalyst and of the leaving group alcohol: a change from general base catalysis to general acid catalysis is proposed. Catalysis of the isomerization requires efficient stabilization of the phosphorane by strong interactions with the catalyst. Catalytic strategies utilised by bimetallic complexes are also briefly discussed.Entities:
Mesh:
Substances:
Year: 2013 PMID: 24135854 DOI: 10.1039/c3ob41554f
Source DB: PubMed Journal: Org Biomol Chem ISSN: 1477-0520 Impact factor: 3.876