Cited by 94Origins and Evolution of LifeRNA and protein synthesis mechanismsDNA and Nucleic Acid Chemistry

Spontaneous Prebiotic Formation of a β-Ribofuranoside That Self-Assembles with a Complementary Heterocycle

Chen, Michael C., Cafferty, Brian J., Mamajanov, Irena, Gállego, Isaac, Khanam, Jaheda, Krishnamurthy, Ramanarayanan, Hud, Nicholas V.·2014·Journal of the American Chemical Society

Abstract

The RNA World hypothesis is central to many current theories regarding the origin and early evolution of life. However, the formation of RNA by plausible prebiotic reactions remains problematic. Formidable challenges include glycosidic bond formation between ribose and the canonical nucleobases, as well as the inability of nucleosides to mutually select their pairing partners from a complex mixture of other molecules prior to polymerization. Here we report a one-pot model prebiotic reaction between a pyrimidine nucleobase (2,4,6-triaminopyrimidine, TAP) and ribose, which produces TAP-ribose conjugates in high yield (60-90%). When cyanuric acid (CA), a plausible ancestral nucleobase, is mixed with a crude TAP+ribose reaction mixture, micrometer-length supramolecular, noncovalent assemblies are formed. A major product of the TAP+ribose reaction is a β-ribofuranoside of TAP, which we term TARC. This nucleoside is also shown to efficiently form supramolecular assemblies in water by pairing and stacking with CA. These results provide a proof-of-concept system demonstrating that several challenges associated with the prebiotic emergence of RNA, or pre-RNA polymers, may not be as problematic as widely believed.

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Crossref · 10.1021/ja410124v

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  • Among more than 80 possible alternative nucleobase candidates, 2,4,6-triaminopyrimidine (TAP) was suggested as having the highest reactivity with ribose, and it forms supramolecular assemblies with complementary heterocycles.

    “From more than 80 possible candidates, 2,4,6-triaminopyrimidine (TAP) was suggested as having the highest reactivity with ribose, and indeed it forms supramolecular assemblies with complementary heterocycles [37,38].”

    From The RNA world as a model system to study the origin of life (2015) · cites this paper as [37]

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Authors
Chen, M. C., Cafferty, B. J., Mamajanov, I., Gállego, I., Khanam, J., Krishnamurthy, R., & Hud, N. V.
Affiliations
  • Georgia Institute of Technology (US)
  • Scripps Research Institute (US)
Corresponding author
Hud, Nicholas V.
Venue
Journal of the American Chemical Society
Published
2013-12-13
Volume
136
Issue
15
Pages
5640-5646
ISSN
  • 0002-7863 (ISSN-L)
  • 1520-5126
OpenAlex
W2071881111
Cited by
94
References
38
Citations by year
2026: 3 · 2025: 6 · 2024: 2 · 2023: 4 · 2022: 9 · 2021: 11 · 2020: 5 · 2019: 6 · 2018: 9 · 2017: 7 · 2016: 12 · 2015: 11 · 2014: 9
FWCI
5.76
Type
journal article
Language
en
Open access
closed
Locations
  • Journal of the American Chemical Society (publishedVersion)
  • PubMed (publishedVersion)
Topics
  • Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › RNA and protein synthesis mechanisms
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › DNA and Nucleic Acid Chemistry
Keywords
RNA world, prebiotic chemistry, 2,4,6-triaminopyrimidine, ribose, cyanuric acid, supramolecular self-assembly, nucleobase pairing, glycosidic bond formation, origin of life
MeSH terms
Furans, Heterocyclic Compounds, Microscopy, Atomic Force, Prebiotics, Carbon-13 Magnetic Resonance Spectroscopy, Proton Magnetic Resonance Spectroscopy

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