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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| Format: | Article |
| Language: | en_US |
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Cold Spring Harbor Laboratory Press
2014
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| Online Access: | http://hdl.handle.net/1721.1/92497 https://orcid.org/0000-0002-8241-4834 https://orcid.org/0000-0002-2196-5691 |
| _version_ | 1826205898646749184 |
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| author | Singh, Vipender Fedeles, Bogdan I. Essigmann, John M. |
| author2 | Massachusetts Institute of Technology. Center for Environmental Health Sciences |
| author_facet | Massachusetts Institute of Technology. Center for Environmental Health Sciences Singh, Vipender Fedeles, Bogdan I. Essigmann, John M. |
| author_sort | Singh, Vipender |
| collection | MIT |
| description | 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. |
| first_indexed | 2024-09-23T13:21:07Z |
| format | Article |
| id | mit-1721.1/92497 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T13:21:07Z |
| publishDate | 2014 |
| publisher | Cold Spring Harbor Laboratory Press |
| record_format | dspace |
| spelling | mit-1721.1/924972022-09-28T13:33:33Z Role of tautomerism in RNA biochemistry Singh, Vipender Fedeles, Bogdan I. Essigmann, John M. Massachusetts Institute of Technology. Center for Environmental Health Sciences Massachusetts Institute of Technology. Department of Biological Engineering Massachusetts Institute of Technology. Department of Chemistry Fedeles, Bogdan I. Singh, Vipender Essigmann, John M. 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. National Institutes of Health (U.S.) (Grant P01 CA26731) National Institutes of Health (U.S.) (Grant R37 CA080024) National Institutes of Health (U.S.) (Grant P30 ES002109) National Institutes of Health (U.S.) (Training Grant T32 ES007020) 2014-12-24T16:09:13Z 2014-12-24T16:09:13Z 2015-01 Article http://purl.org/eprint/type/JournalArticle 1355-8382 1469-9001 http://hdl.handle.net/1721.1/92497 Singh, V., B. I. Fedeles, and J. M. Essigmann. “Role of Tautomerism in RNA Biochemistry.” RNA 21, no. 1 (December 16, 2014): 1–13. https://orcid.org/0000-0002-8241-4834 https://orcid.org/0000-0002-2196-5691 en_US http://dx.doi.org/10.1261/rna.048371.114 RNA Creative Commons Attribution http://creativecommons.org/licenses/by-nc/4.0/ application/pdf Cold Spring Harbor Laboratory Press Cold Spring Harbor Laboratory Press |
| spellingShingle | Singh, Vipender Fedeles, Bogdan I. Essigmann, John M. Role of tautomerism in RNA biochemistry |
| title | Role of tautomerism in RNA biochemistry |
| title_full | Role of tautomerism in RNA biochemistry |
| title_fullStr | Role of tautomerism in RNA biochemistry |
| title_full_unstemmed | Role of tautomerism in RNA biochemistry |
| title_short | Role of tautomerism in RNA biochemistry |
| title_sort | role of tautomerism in rna biochemistry |
| url | http://hdl.handle.net/1721.1/92497 https://orcid.org/0000-0002-8241-4834 https://orcid.org/0000-0002-2196-5691 |
| work_keys_str_mv | AT singhvipender roleoftautomerisminrnabiochemistry AT fedelesbogdani roleoftautomerisminrnabiochemistry AT essigmannjohnm roleoftautomerisminrnabiochemistry |