Literature DB >> 24135854

There is no universal mechanism for the cleavage of RNA model compounds in the presence of metal ion catalysts.

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


  5 in total

Review 1.  Altered (transition) states: mechanisms of solution and enzyme catalyzed RNA 2'-O-transphosphorylation.

Authors:  Daniel L Kellerman; Darrin M York; Joseph A Piccirilli; Michael E Harris
Journal:  Curr Opin Chem Biol       Date:  2014-07-12       Impact factor: 8.822

2.  Isotope effect analyses provide evidence for an altered transition state for RNA 2'-O-transphosphorylation catalyzed by Zn(2+).

Authors:  Shuming Zhang; Hong Gu; Haoyuan Chen; Emily Strong; Edward W Ollie; Daniel Kellerman; Danni Liang; Masaru Miyagi; Vernon E Anderson; Joseph A Piccirilli; Darrin M York; Michael E Harris
Journal:  Chem Commun (Camb)       Date:  2016-03-25       Impact factor: 6.222

3.  Metal ion-promoted cleavage of nucleoside diphosphosugars: a model for reactions of phosphodiester bonds in carbohydrates.

Authors:  Meisa Dano; Marjukka Elmeranta; David R W Hodgson; Juho Jaakkola; Heidi Korhonen; Satu Mikkola
Journal:  J Biol Inorg Chem       Date:  2015-11-07       Impact factor: 3.358

Review 4.  Mechanistic Studies of Homo- and Heterodinuclear Zinc Phosphoesterase Mimics: What Has Been Learned?

Authors:  Andrea Erxleben
Journal:  Front Chem       Date:  2019-02-21       Impact factor: 5.221

Review 5.  Phosphodiester models for cleavage of nucleic acids.

Authors:  Satu Mikkola; Tuomas Lönnberg; Harri Lönnberg
Journal:  Beilstein J Org Chem       Date:  2018-04-10       Impact factor: 2.883

  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.