Stability and Reactivity of Cyclopentane Nucleoside Analogs in 98% w/w Sulfuric Acid
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molecules-31-01003.pdf
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Author(s)
Seager, Sara
Seager, Maxwell D.
Visser, Ton
Marinus, Nittert
Poizat, Mael
van Wiltenburg, Jim
Poelert, Martin
Petkowski, Janusz J.
Date Issued
March 17, 2026
Journal
Molecules
Publisher
Multidisciplinary Digital Publishing Institute
Citation
Seager, S., Seager, M. D., Visser, T., Marinus, N., Poizat, M., van Wiltenburg, J., Poelert, M., & Petkowski, J. J. (2026). Stability and Reactivity of Cyclopentane Nucleoside Analogs in 98% w/w Sulfuric Acid. Molecules, 31(6), 1003.
Version
Final published version
Abstract
We synthesized seven carbocyclic nucleoside analogs featuring a cyclopentane ring in place of the (deoxy)ribose sugar, which serves as a linker in DNA/RNA nucleosides. We assessed the stability of cyclopentane nucleosides in 98% w/w sulfuric acid at room temperature via 1H and 13C NMR spectroscopy. We observe that adenine (A1, A4), guanine (G1) and thymine (T1) cyclopentane nucleoside analogs remain stable for at least two weeks at room temperature, with only minor (~4%) degradation in A1. In contrast, the cytosine analog (C1) rapidly degrades to release a soluble cytosine. Methyl-substituted adenine analogs mimicking polymer backbone attachments at positions prone to tertiary carbocation formation (A2, A3) prove unstable and release soluble adenine. Only the 3,3-dimethylcyclopentyl adenine analog (A4) exhibits sufficient stability. Our findings reveal that cyclopentane serves as a viable stable linker in concentrated sulfuric acid for select nucleic acid bases, provided that the backbone connections avoid tertiary carbons susceptible to carbocation-mediated cleavage. We thus identify one potential key structural feature for engineering examples of genetic-like polymers that could potentially persist in Venus’s concentrated sulfuric acid cloud environment.
MIT Department
Massachusetts Institute of Technology. Department of Earth, Atmospheric, and Planetary Sciences
Massachusetts Institute of Technology. Department of Physics
Massachusetts Institute of Technology. Department of Aeronautics and Astronautics
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DOI of Published Version
https://doi.org/10.3390/molecules31061003
