Efficient self-assembly in water of long noncovalent polymers by nucleobase analogues
Abstract
Molecular self-assembly is widely appreciated to result from a delicate balance between several noncovalent interactions and solvation effects. However, current design approaches for achieving self-assembly in water with small, synthetic molecules do not consider all aspects of the hydrophobic effect, in particular the requirement of surface areas greater than 1 nm(2) for an appreciable free energy of hydration. With the concept of a minimum hydrophobic surface area in mind, we designed a system that achieves highly cooperative self-assembly in water. Two weakly interacting low-molecular-weight monomers (cyanuric acid and a modified triaminopyrimidine) are shown to form extremely long supramolecular polymer assemblies that retain water solubility. The complete absence of intermediate assemblies means that the observed equilibrium is between free monomers and supramolecular assemblies. These observations are in excellent agreement with literature values for the free energy of nucleic acid base interactions as well as the calculated free energy penalty for the exposure of hydrophobic structures in water. The results of our study have implications for the design of new self-assembling structures and hydrogel-forming molecules and may provide insights into the origin of the first RNA-like polymers.
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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 [38]
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Self-citation
- Authors
- Cafferty, B. J., Gállego, I., Chen, M. C., Farley, K. I., Eritja, R., & Hud, N. V.
- Affiliations
- Georgia Institute of Technology (US)
- Department of Chemistry and Biochemistry, Parker H. Petit Institute for Bioengineering and Bioscience, Georgia Institute of Technology, Atlanta, Georgia 30332-0400, United States
- Institute for Research in Biomedicine, Parc Científic de Barcelona, Barcelona 08028, Spain
- Corresponding author
- Hud, Nicholas V.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2013-02-08
- Volume
- 135
- Issue
- 7
- Pages
- 2447-2450
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2060840559
- Cited by
- 157
- References
- 29
- Citations by year
- 2026: 4 · 2025: 4 · 2024: 6 · 2023: 4 · 2022: 15 · 2021: 12 · 2020: 7 · 2019: 16 · 2018: 15 · 2017: 8 · 2016: 22 · 2015: 20 · 2014: 17 · 2013: 7
- FWCI
- 8.40
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of the American Chemical Society (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Physical Sciences › Materials Science › Biomaterials › Supramolecular Self-Assembly in Materials
- Physical Sciences › Chemistry › Organic Chemistry › Supramolecular Chemistry and Complexes
- Physical Sciences › Chemistry › Organic Chemistry › Advanced Polymer Synthesis and Characterization
- Keywords
- self-assembly in water, nucleobase analogs, hydrophobic effect, hydration free energy, cyanuric acid, triaminopyrimidine, supramolecular polymers, water-soluble polymers, cooperative self-assembly
- MeSH terms
- Models, Molecular, Nucleic Acids, Polymers, Pyrimidines, Triazines, Water, Macromolecular Substances, Hydrophobic and Hydrophilic Interactions
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