Jump to main content
Jump to site search

Issue 33, 2012
Previous Article Next Article

Intracomplex general acid/base catalyzed cleavage of RNA phosphodiester bonds: the leaving group effect

Author affiliations

Abstract

The general acid/base catalyzed cleavage of a number of alkyl esters of uridine-3′- (and -5′-)phosphate has been studied by utilizing a cleaving agent, in which the catalytic moiety (a substituted 1,3,5-triazine) is tethered to an anchoring ZnII:cyclen moiety. Around pH 7, formation of a strong ternary complex between uracil, ZnII and cyclen brings the general acid/base catalyst close to the scissile phosphodiester linkage, resulting in rate acceleration of 1–2 orders of magnitude with the uridine-3′-phosphodiesters. Curiously, no acceleration was observed with their 5′-counterparts. A βlg value of −0.7 has been determined for the general acid/base catalyzed cleavage, consistent with a proton transfer to the leaving group in the rate-limiting step.

Graphical abstract: Intracomplex general acid/base catalyzed cleavage of RNA phosphodiester bonds: the leaving group effect

Back to tab navigation

Supplementary files

Publication details

The article was received on 18 May 2012, accepted on 11 Jul 2012 and first published on 13 Jul 2012


Article type: Paper
DOI: 10.1039/C2OB25958C
Citation: Org. Biomol. Chem., 2012,10, 6785-6791
  •   Request permissions

    Intracomplex general acid/base catalyzed cleavage of RNA phosphodiester bonds: the leaving group effect

    T. Lönnberg and M. Luomala, Org. Biomol. Chem., 2012, 10, 6785
    DOI: 10.1039/C2OB25958C

Search articles by author

Spotlight

Advertisements