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Base pairing and mutagenesis: observation of a protonated base pair between 2-aminopurine and cytosine in an oligonucleotide by proton NMR.
Open accessAbstract
2-Aminopurine (AP), a potent mutagenic base analogue, most frequently pairs with thymine. In the AP X T base pair, both bases adopt normal tautomeric forms. The mechanism for the mutagenic activity arises from its observed pairing with cytosine, which has been ascribed to an enhanced tendency to adopt the rare imino tautomeric form. NMR studies in H2O on all the exchangeable protons in an oligonucleotide duplex containing an AP X T base pair show Watson-Crick hydrogen bonding. When the thymine is replaced by cytosine in the duplex, we observe an AP X C base pair. Both amino protons of AP are seen excluding the rare tautomeric form. Although several alternative structures are possible, it is shown that the second hydrogen bond is formed by protonation of the AP X C base pair and that this is the dominant species under physiological conditions.
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Cited by
Biochemical Basis of DNA Replication Fidelity
Goodman, M. F., Creighton, S., Bloom, L. B., Petruska, J., & Kunkel, T. A. (1993) · Critical Reviews in Biochemistry and Molecular Biology · doi:10.3109/10409239309086792 · Cited by 446
Self-citationDNA damage by reactive species: Mechanisms, mutation and repair
Jena, N. R. (2012) · Journal of Biosciences · doi:10.1007/s12038-012-9218-2 · Cited by 344
Moran, S., Ren, R. X.-F., Rumney, & Kool, E. T. (1997) · Journal of the American Chemical Society · doi:10.1021/ja963718g · Cited by 317
Lukin, M., & de los Santos, C. (2006) · Chemical Reviews · doi:10.1021/cr0404646 · Cited by 158
Primitive selection of the fittest emerging through functional synergy in nucleopeptide networks
Bandela, A. K., Wagner, N., Sadihov, H., Morales-Reina, S., Chotera-Ouda, A., Basu, K., Cohen-Luria, R., de la Escosura, A., & Ashkenasy, G. (2021) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.2015285118 · Cited by 49
Metadata
- Authors
- Sowers, L. C., Fazakerley, G. V., Eritja, R., Kaplan, B. E., & Goodman, M. F.
- Venue
- Proceedings of the National Academy of Sciences
- Published
- 1986-08
- Volume
- 83
- Issue
- 15
- Pages
- 5434-5438
- ISSN
- 0027-8424 (ISSN-L)
- 1091-6490
- OpenAlex
- W2091751711
- Cited by
- 204
- References
- 0
- FWCI
- 1.52
- Type
- journal article
- Language
- en
- Open access
- green
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- CoChat. (2026). Citation check: Base pairing and mutagenesis: observation of a protonated base pair between 2-aminopurine and cytosine in an oligonucleotide by proton NMR. https://app.cochat.ai/papers/10.1073/pnas.83.15.5434
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- Sowers, L. C., Fazakerley, G. V., Eritja, R., Kaplan, B. E., & Goodman, M. F. (1986). Base pairing and mutagenesis: observation of a protonated base pair between 2-aminopurine and cytosine in an oligonucleotide by proton NMR. Proceedings of the National Academy of Sciences. https://doi.org/10.1073/pnas.83.15.5434
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