Spontaneous Symmetry Breaking in the Formation of Supramolecular Polymers: Implications for the Origin of Biological Homochirality
Abstract
Aqueous solutions of the achiral, monomeric, nucleobase mimics (2,4,6‐triaminopyrimidine, TAP, and a cyanuric acid derivative, CyCo6) spontaneously assemble into macroscopic homochiral domains of supramolecular polymers. These assemblies exhibit a high degree of chiral amplification. Addition of a small quantity of one handedness of a chiral derivative of CyCo6 generates exclusively homochiral structures. This system exhibits the highest reported degree of chiral amplification for dynamic helical polymers or supramolecular helices. Significantly, homochiral polymers comprised of hexameric rosettes with structural features that resemble nucleic acids are formed from mixtures of cyanuric acid (Cy) and ribonucleotides ( l‐, d ‐pTARC) that arise spontaneously from the reaction of TAP with the sugars. These findings support the hypothesis that nucleic acid homochirality was a result of symmetry breaking at the supramolecular polymer level.
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Synthetic polymers embedding a modestly biased racemic mixture of enantiomers adopt a single-handed helical conformation thanks to the 'majority-rules' effect.
“synthetic polymers embedding a modestly biased racemic mixture of enantiomers adopt a single-handed helical conformation thanks to the so-called ''majority-rules'' effect.”
From Possible chemical and physical scenarios towards biological homochirality (2022) · cites this paper as [565]
Cites
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Self-citationChen, M. C., Cafferty, B. J., Mamajanov, I., Gállego, I., Khanam, J., Krishnamurthy, R., & Hud, N. V. (2014) · Journal of the American Chemical Society · doi:10.1021/ja410124v · Cited by 94 · see citing works
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Possible chemical and physical scenarios towards biological homochirality
Sallembien, Q., Bouteiller, L., Crassous, J., & Raynal, M. (2022) · Chemical Society Reviews · doi:10.1039/d1cs01179k · Cited by 186 · see citing works
Symmetry Breaking in Self-Assembled Nanoassemblies
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- Authors
- Karunakaran, S. C., Cafferty, B. J., Weigert‐Muñoz, A., Schuster, G. B., & Hud, N. V.
- Affiliations
- Georgia Institute of Technology (US)
- School of Chemistry and Biochemistry Parker H. Petit Institute for Bioengineering and Bioscience Georgia Institute of Technology USA
- Corresponding author
- Hud, Nicholas V.
- ORCID
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2019-01-02
- Volume
- 58
- Issue
- 5
- Pages
- 1453-1457
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W2903887832
- Cited by
- 86
- References
- 4
- Citations by year
- 2026: 8 · 2025: 6 · 2024: 9 · 2023: 12 · 2022: 13 · 2021: 11 · 2020: 15 · 2019: 12
- FWCI
- 5.09
- Type
- journal article
- Language
- en
- Open access
- closed
- Licence
- Locations
- Angewandte Chemie International Edition (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Science Foundation (CHE-1504217)
- Topics
- Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
- Physical Sciences › Chemistry › Organic Chemistry › Supramolecular Chemistry and Complexes
- Physical Sciences › Materials Science › Biomaterials › Supramolecular Self-Assembly in Materials
- Keywords
- spontaneous symmetry breaking, supramolecular polymers, homochirality, origin of homochirality, 2,4,6-triaminopyrimidine, cyanuric acid derivatives, chiral amplification, nucleic acid mimics, ribonucleotides, prebiotic chemistry
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