Issue 3, 2012
From the journal:

Organic & Biomolecular Chemistry

Impact of steric constraints on the product distribution of phosphate-branched oligonucleotide models of the large ribozymes†

Tuomas Lönnberg*a  and  Kirsi-Maria Keroa  

* Corresponding authors

a Department of Chemistry, University of Turku, Turku, Finland
E-mail: tuanlo@utu.fi
Fax: +358 2 333 6700
Tel: +358 2 333 6777

Abstract

To assess the extent to which steric constraints may influence the product distribution of the reactions of the large ribozymes, phosphate-branched oligonucleotides of varying length and sequence have been synthesized and their alkaline hydrolysis studied over a wide temperature range. At low temperatures, the branching trinucleoside-3′,3′,5′-monophosphate moiety is hydrolyzed almost exclusively by P–O3′ fission. At higher temperatures, P–O5′ fission competes, accounting at most for 22% of the overall reaction. The results suggest that steric constraints imposed by the secondary structure of the reaction site may significantly contribute to the observed regioselectivity of the transesterification reactions catalyzed by the large ribozymes.

Graphical abstract: Impact of steric constraints on the product distribution of phosphate-branched oligonucleotide models of the large ribozymes

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Article information

DOI
https://doi.org/10.1039/C1OB06399E
Article type
Paper
Submitted
16 Aug 2011
Accepted
05 Oct 2011
First published
05 Oct 2011

Org. Biomol. Chem., 2012,10, 569-574

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Impact of steric constraints on the product distribution of phosphate-branched oligonucleotide models of the large ribozymes

T. Lönnberg and K. Kero, Org. Biomol. Chem., 2012, 10, 569 DOI: 10.1039/C1OB06399E

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