Role of tautomerism in RNA biochemistry

Heterocyclic nucleic acid bases and their analogs can adopt multiple tautomeric forms due to the presence of multiple solvent-exchangeable protons. In DNA, spontaneous formation of minor tautomers has been speculated to contribute to mutagenic mispairings during DNA replication, whereas in RNA, mino...

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Bibliographic Details
Published in:RNA (Cambridge) 2015-01, Vol.21 (1), p.1-13
Main Authors: Singh, Vipender, Fedeles, Bogdan I, Essigmann, John M
Format: Article
Language:English
Subjects:
Aptamers, Nucleotide - chemistry
Binding Sites
Biocatalysis
Isomerism
Models, Molecular
Oxidation-Reduction
Review
Riboswitch
RNA - chemistry
RNA, Catalytic - chemistry
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Summary:Heterocyclic nucleic acid bases and their analogs can adopt multiple tautomeric forms due to the presence of multiple solvent-exchangeable protons. In DNA, spontaneous formation of minor tautomers has been speculated to contribute to mutagenic mispairings during DNA replication, whereas in RNA, minor tautomeric forms have been proposed to enhance the structural and functional diversity of RNA enzymes and aptamers. This review summarizes the role of tautomerism in RNA biochemistry, specifically focusing on the role of tautomerism in catalysis of small self-cleaving ribozymes and recognition of ligand analogs by riboswitches. Considering that the presence of multiple tautomers of nucleic acid bases is a rare occurrence, and that tautomers typically interconvert on a fast time scale, methods for studying rapid tautomerism in the context of nucleic acids under biologically relevant aqueous conditions are also discussed.
ISSN:1355-8382
1469-9001
DOI:10.1261/rna.048371.114