Pentopyranosyl Oligonucleotide Systems. 9th Communication: The β ‐ D ‐Ribopyranosyl‐(4′→2′)‐oligonucleotide System (‘Pyranosyl‐RNA’): Synthesis and Resumé of Base‐Pairing Properties
Open accessAbstract
Pyranosyl‐RNA (‘p‐RNA’ ) is an oligonucleotide system isomeric to natural RNA and composed of the very same building blocks as RNA. Its generational, chemical, and informational properties are deemed to be those of an alternative nucleic acid system that could have been a candidate in Nature's evolutionary choice of the molecular basis of genetic function. We consider the study of the chemistry of p‐RNA as etiologically relevant in the sense that knowledge of its structural, chemical, and informational properties on the chemical level offers both a perspective and reference points for the recognition of specific structural assets of the RNA structure that made it the (supposedly) superior system among possible alternatives and, therefore, the system that became part of biology as we know it today. The paper describes the chemical synthesis of β ‐ d‐ (and L )‐ribopyranosyl‐(4′→2′)‐oligonucleotide sequences, presents a resume of their structural and chemical properties, and cautiously discusses what we may and may not have learned from the pyranosyl isomer of RNA with respect to the conundrum of RNA's origin.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
p-RNAs are less likely than the corresponding RNAs to form multiple-strand competing structures.
“p-RNAs are less likely than the corresponding RNAs to form multiple-strand competing structures”
From Protocells and RNA Self-Replication (2018) · cites this paper as Pitsch et al. 2003
Polynucleotides based on the pyranosyl analog of ribose (p-RNA) form Watson-Crick-paired double helices that are more stable than RNA.
“polynucleotides based on the pyranosyl analog of ribose (p-RNA) form Watson-Crick-paired double helices that are more stable than RNA”
From Protocells and RNA Self-Replication (2018) · cites this paper as Pitsch et al. 2003
p-RNA helices twist much more gradually than those of standard nucleic acids.
“the helices twist much more gradually than those of standard nucleic acids”
From Protocells and RNA Self-Replication (2018) · cites this paper as Pitsch et al. 2003
Cites
RNA-catalyzed RNA polymerization: Accurate and general RNA-templated primer extension.
Johnston, W. K., Unrau, P. J., Lawrence, M. S., Glasner, M. E., & Bartel, D. P. (2001) · Science · doi:10.1126/science.1060786 · Cited by 768 · see citing works
Chemical etiology of nucleic acid structure
Eschenmoser, A. (1999) · Science · doi:10.1126/science.284.5423.2118 · Cited by 611 · see citing works
Self-citationA chiroselective peptide replicator
Saghatelian, A., Yokobayashi, Y., Soltani, K., & Ghadiri, M. R. (2001) · Nature · doi:10.1038/35057238 · Cited by 310 · see citing works
Bolli, M., Micura, R., & Eschenmoser, A. (1997) · Chemistry & Biology · doi:10.1016/s1074-5521(97)90074-0 · Cited by 290 · see citing works
Self-citationThe limits of template-directed synthesis with nucleoside-5′-phosphoro(2-methyl)imidazolides
Hill, A. R., Orgel, L. E., & Wu, T. (1993) · Origins of life and evolution of the biosphere · doi:10.1007/bf01582078 · Cited by 92 · see citing works
Flagged first, then by citations
Cited by
Sorted by citations
Prebiotic chemistry and the origin of the RNA world.
Leslie E., O. (2004) · Critical Reviews in Biochemistry and Molecular Biology · doi:10.1080/10409230490460765 · Cited by 1,124 · see citing works
Robertson, M. P., & Joyce, G. F. (2012) · Cold Spring Harbor Perspectives in Biology · doi:10.1101/cshperspect.a003608 · Cited by 556 · see citing works
Protocells and RNA Self-Replication
Joyce, G. F., & Szostak, J. W. (2018) · Cold Spring Harbor Perspectives in Biology · doi:10.1101/cshperspect.a034801 · Cited by 308 · see citing works
- Authors
- Pitsch, S., Wendeborn, S., Krishnamurthy, R., Holzner, A., Minton, M., Bolli, M., Miculca, C., Windhab, N., Micura, R., Stanek, M., Jaun, B., & Eschenmoser, A.
- Affiliations
- Scripps Research Institute (US)
- Goethe University Frankfurt (DE)
- ORCID
- Venue
- Helvetica Chimica Acta
- Publisher
- Wiley
- Published
- 2003-12
- Volume
- 86
- Issue
- 12
- Pages
- 4270-4363
- ISSN
- 0018-019X (ISSN-L)
- 1522-2675
- OpenAlex
- W2070271351
- Cited by
- 55
- References
- 5
- Citations by year
- 2026: 2 · 2025: 1 · 2024: 2 · 2023: 3 · 2022: 1 · 2019: 3 · 2018: 3 · 2017: 2 · 2015: 5 · 2014: 4 · 2013: 1 · 2012: 1
- FWCI
- 0.81
- Type
- journal article
- Language
- en
- Open access
- green
- infoscience.epfl.ch
- Locations
- Helvetica Chimica Acta (publishedVersion)
- Infoscience (Ecole Polytechnique Fédérale de Lausanne) (submittedVersion)
- Infoscience (Ecole Polytechnique Fédérale de Lausanne) (submittedVersion, cc-by-nc-nd)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › DNA and Nucleic Acid Chemistry
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › RNA and protein synthesis mechanisms
- Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
- Keywords
- chemical synthesis, oligonucleotide structure, nucleic acid evolution
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
