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Efficient Self-Assembly in Water of Long Noncovalent Polymers by Nucleobase Analogues

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    Efficient Self-Assembly in Water of Long Noncovalent Polymers by Nucleobase Analogues
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    † 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
    [email protected]
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    Cite this: J. Am. Chem. Soc. 2013, 135, 7, 2447–2450
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    https://doi.org/10.1021/ja312155v
    Published February 8, 2013
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    Abstract

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    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 nm2 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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    2. Asem Alenaizan. Structural Analysis of the Poly(thymidine)–Melamine Assembly. The Journal of Physical Chemistry B 2022, 126 (36) , 6948-6954. https://doi.org/10.1021/acs.jpcb.2c04665
    3. Jessica M. Weber, Tho H. Tran. Synthesizing Bioactive Molecules: Synergies between Drug Discovery Techniques and Astrobiology Research. ACS Earth and Space Chemistry 2022, 6 (5) , 1213-1220. https://doi.org/10.1021/acsearthspacechem.1c00326
    4. Syed Pavel Afrose, Chiranjit Mahato, Pooja Sharma, Lisa Roy, Dibyendu Das. Nonequilibrium Catalytic Supramolecular Assemblies of Melamine- and Imidazole-Based Dynamic Building Blocks. Journal of the American Chemical Society 2022, 144 (2) , 673-678. https://doi.org/10.1021/jacs.1c11457
    5. Sarabjeet Kaur, Payal Grover, Stacey D. Wetmore, Purshotam Sharma. Role of Stacking Interactions in the Stability of Primitive Genetics: A Quantum Chemical View. Journal of Chemical Information and Modeling 2021, 61 (9) , 4321-4330. https://doi.org/10.1021/acs.jcim.1c00276
    6. Sagar Biswas, Tapas Ghosh, Deepak K. K. Kori, Apurba K. Das. Bicomponent Coassembled Hydrogel as a Template for Selective Enzymatic Generation of DOPA. Langmuir 2021, 37 (37) , 10883-10889. https://doi.org/10.1021/acs.langmuir.1c00438
    7. David M. Fialho, Suneesh C. Karunakaran, Katherine W. Greeson, Isaac Martínez, Gary B. Schuster, Ramanarayanan Krishnamurthy, Nicholas V. Hud. Depsipeptide Nucleic Acids: Prebiotic Formation, Oligomerization, and Self-Assembly of a New Proto-Nucleic Acid Candidate. Journal of the American Chemical Society 2021, 143 (34) , 13525-13537. https://doi.org/10.1021/jacs.1c02287
    8. Shiqin Miao, Debmalya Bhunia, Shekaraiah Devari, Yufeng Liang, Oliver Munyaradzi, Sarah Rundell, Dennis Bong. Bifacial PNAs Destabilize MALAT1 by 3′ A-Tail Displacement from the U-Rich Internal Loop. ACS Chemical Biology 2021, 16 (8) , 1600-1609. https://doi.org/10.1021/acschembio.1c00575
    9. Gary B. Schuster, Brian J. Cafferty, Suneesh C. Karunakaran, Nicholas V. Hud. Water-Soluble Supramolecular Polymers of Paired and Stacked Heterocycles: Assembly, Structure, Properties, and a Possible Path to Pre-RNA. Journal of the American Chemical Society 2021, 143 (25) , 9279-9296. https://doi.org/10.1021/jacs.0c13081
    10. Asem Alenaizan, Carlos H. Borca, Suneesh C. Karunakaran, Amy K. Kendall, Gerald Stubbs, Gary B. Schuster, C. David Sherrill, Nicholas V. Hud. X-ray Fiber Diffraction and Computational Analyses of Stacked Hexads in Supramolecular Polymers: Insight into Self-Assembly in Water by Prospective Prebiotic Nucleobases. Journal of the American Chemical Society 2021, 143 (16) , 6079-6094. https://doi.org/10.1021/jacs.0c12010
    11. David M. Fialho, Tyler P. Roche, Nicholas V. Hud. Prebiotic Syntheses of Noncanonical Nucleosides and Nucleotides. Chemical Reviews 2020, 120 (11) , 4806-4830. https://doi.org/10.1021/acs.chemrev.0c00069
    12. Bin Liu, Charalampos G. Pappas, Jim Ottelé, Gaël Schaeffer, Christoph Jurissek, Priscilla F. Pieters, Meniz Altay, Ivana Marić, Marc C. A. Stuart, Sijbren Otto. Spontaneous Emergence of Self-Replicating Molecules Containing Nucleobases and Amino Acids. Journal of the American Chemical Society 2020, 142 (9) , 4184-4192. https://doi.org/10.1021/jacs.9b10796
    13. Andre N. Petelski, Célia Fonseca Guerra. Hydrogen-Bonded Rosettes of Aminotriazines for Selective-Ion Recognition. The Journal of Physical Chemistry C 2020, 124 (5) , 3352-3363. https://doi.org/10.1021/acs.jpcc.9b09366
    14. Suneesh C. Karunakaran, Brian J. Cafferty, Kyan S. Jain, Gary B. Schuster, Nicholas V. Hud. Reversible Transformation of a Supramolecular Hydrogel by Redox Switching of Methylene Blue—A Noncovalent Chain Stopper. ACS Omega 2020, 5 (1) , 344-349. https://doi.org/10.1021/acsomega.9b02785
    15. Violeta Vázquez-González, Maria J. Mayoral, Raquel Chamorro, Marco M. R. M. Hendrix, Ilja K. Voets, David González-Rodríguez. Noncovalent Synthesis of Self-Assembled Nanotubes through Decoupled Hierarchical Cooperative Processes. Journal of the American Chemical Society 2019, 141 (41) , 16432-16438. https://doi.org/10.1021/jacs.9b07868
    16. Lafayette N. J. de Windt, Chidambar Kulkarni, Huub M. M. ten Eikelder, Albert J. Markvoort, E. W. Meijer, Anja R. A. Palmans. Detailed Approach to Investigate Thermodynamically Controlled Supramolecular Copolymerizations. Macromolecules 2019, 52 (19) , 7430-7438. https://doi.org/10.1021/acs.macromol.9b01502
    17. Takehiro Hirao, Naoyuki Hisano, Shigehisa Akine, Shin-ichi Kihara, Takeharu Haino. Ring–Chain Competition in Supramolecular Polymerization Directed by Molecular Recognition of the Bisporphyrin Cleft. Macromolecules 2019, 52 (16) , 6160-6168. https://doi.org/10.1021/acs.macromol.9b01012
    18. Shiqin Miao, Yufeng Liang, Ila Marathe, Jie Mao, Chris DeSantis, Dennis Bong. Duplex Stem Replacement with bPNA+ Triplex Hybrid Stems Enables Reporting on Tertiary Interactions of Internal RNA Domains. Journal of the American Chemical Society 2019, 141 (23) , 9365-9372. https://doi.org/10.1021/jacs.9b03435
    19. Marco Todisco, Tommaso P. Fraccia, Greg P. Smith, Andrea Corno, Lucas Bethge, Sven Klussmann, Elvezia M. Paraboschi, Rosanna Asselta, Diego Colombo, Giuliano Zanchetta, Noel A. Clark, Tommaso Bellini. Nonenzymatic Polymerization into Long Linear RNA Templated by Liquid Crystal Self-Assembly. ACS Nano 2018, 12 (10) , 9750-9762. https://doi.org/10.1021/acsnano.8b05821
    20. Hiromu Kashida, Yuhei Hattori, Kaho Tazoe, Tadashi Inoue, Keiji Nishikawa, Kentaro Ishii, Susumu Uchiyama, Hayato Yamashita, Masayuki Abe, Yukiko Kamiya, Hiroyuki Asanuma. Bifacial Nucleobases for Hexaplex Formation in Aqueous Solution. Journal of the American Chemical Society 2018, 140 (27) , 8456-8462. https://doi.org/10.1021/jacs.8b02807
    21. Jie Mao, Chris DeSantis, and Dennis Bong . Small Molecule Recognition Triggers Secondary and Tertiary Interactions in DNA Folding and Hammerhead Ribozyme Catalysis. Journal of the American Chemical Society 2017, 139 (29) , 9815-9818. https://doi.org/10.1021/jacs.7b05448
    22. Tommaso P. Fraccia, Gregory P. Smith, Lucas Bethge, Giuliano Zanchetta, Giovanni Nava, Sven Klussmann, Noel A. Clark, and Tommaso Bellini . Liquid Crystal Ordering and Isotropic Gelation in Solutions of Four-Base-Long DNA Oligomers. ACS Nano 2016, 10 (9) , 8508-8516. https://doi.org/10.1021/acsnano.6b03622
    23. Gretchen Marie Peters, Luke P. Skala, and Jeffery T. Davis . A Molecular Chaperone for G4-Quartet Hydrogels. Journal of the American Chemical Society 2016, 138 (1) , 134-139. https://doi.org/10.1021/jacs.5b08769
    24. Xuewen Du, Jie Zhou, Junfeng Shi, and Bing Xu . Supramolecular Hydrogelators and Hydrogels: From Soft Matter to Molecular Biomaterials. Chemical Reviews 2015, 115 (24) , 13165-13307. https://doi.org/10.1021/acs.chemrev.5b00299
    25. Marshall R. Ligare, Anouk M. Rijs, Giel Berden, Martin Kabeláč, Dana Nachtigallova, Jos Oomens, and Mattanjah S. de Vries . Resonant Infrared Multiple Photon Dissociation Spectroscopy of Anionic Nucleotide Monophosphate Clusters. The Journal of Physical Chemistry B 2015, 119 (25) , 7894-7901. https://doi.org/10.1021/acs.jpcb.5b02222
    26. Gretchen Marie Peters, Luke P. Skala, Taylor N. Plank, Hyuntaek Oh, G. N. Manjunatha Reddy, Andrew Marsh, Steven P. Brown, Srinivasa R. Raghavan, and Jeffery T. Davis . G4-Quartet·M+ Borate Hydrogels. Journal of the American Chemical Society 2015, 137 (17) , 5819-5827. https://doi.org/10.1021/jacs.5b02753
    27. Zhuo Li, Yu-Fang Wang, Bin Liu, Tian-Yu Zheng, Shi-Chao Zhang, and Jian-She Zhao . Pressure-Dependent Pseudo-Polymorphism of Polymeric {[Cu2(TBA)]·2H2O}n and Dinuclear [Cu2(TBA)(H2O)2]·2H2O Complexes Based on in Situ Tetramerization of DMBA. Crystal Growth & Design 2014, 14 (11) , 5640-5646. https://doi.org/10.1021/cg500935a
    28. Gretchen Marie Peters, Luke P. Skala, Taylor N. Plank, Brooke J. Hyman, G. N. Manjunatha Reddy, Andrew Marsh, Steven P. Brown, and Jeffery T. Davis . A G4·K+ Hydrogel Stabilized by an Anion. Journal of the American Chemical Society 2014, 136 (36) , 12596-12599. https://doi.org/10.1021/ja507506c
    29. Jiang-Fei Xu, Li-Ya Niu, Yu-Zhe Chen, Li-Zhu Wu, Chen-Ho Tung, and Qing-Zheng Yang . Hydrogen Bonding Directed Self-Assembly of Small-Molecule Amphiphiles in Water. Organic Letters 2014, 16 (15) , 4016-4019. https://doi.org/10.1021/ol501841f
    30. Xin Xia, Xijun Piao, and Dennis Bong . Bifacial Peptide Nucleic Acid as an Allosteric Switch for Aptamer and Ribozyme Function. Journal of the American Chemical Society 2014, 136 (20) , 7265-7268. https://doi.org/10.1021/ja5032584
    31. Michael C. Chen, Brian J. Cafferty, Irena Mamajanov, Isaac Gállego, Jaheda Khanam, Ramanarayanan Krishnamurthy, and Nicholas V. Hud . Spontaneous Prebiotic Formation of a β-Ribofuranoside That Self-Assembles with a Complementary Heterocycle. Journal of the American Chemical Society 2014, 136 (15) , 5640-5646. https://doi.org/10.1021/ja410124v
    32. Xijun Piao, Xin Xia, and Dennis Bong . Bifacial Peptide Nucleic Acid Directs Cooperative Folding and Assembly of Binary, Ternary, and Quaternary DNA Complexes. Biochemistry 2013, 52 (37) , 6313-6323. https://doi.org/10.1021/bi4008963
    33. M. Tassilo Fenske, Wolfgang Meyer-Zaika, Hans-Gert Korth, Henning Vieker, Andrey Turchanin, and Carsten Schmuck . Cooperative Self-Assembly of Discoid Dimers: Hierarchical Formation of Nanostructures with a pH Switch. Journal of the American Chemical Society 2013, 135 (22) , 8342-8349. https://doi.org/10.1021/ja4025148
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    35. Syed Pavel Afrose, Soumili Roy, Pratip Bhattacharyya, Ajeet Kumar Singh, Lisa Roy, Dibyendu Das. Minimal catalytic dissipative assemblies via cooperation of an amino acid, a nucleobase precursor and a cofactor. Chemical Science 2025, 326 https://doi.org/10.1039/D5SC00827A
    36. Yungang Feng, Fangrui Xie, Rui Ding, Qingrong Zhang, Youzhi Zeng, Li Li, Lianbin Wu, Yunlong Yu, Linxuan Fang. One-pot rapid preparation of long-term antioxidant and antibacterial biomedical gels based on lipoic acid and eugenol for accelerating cutaneous wound healing. Journal of Materials Chemistry B 2024, 12 (48) , 12641-12651. https://doi.org/10.1039/D4TB01844C
    37. Nikita Orekhov, Nina Bukhtiiarova, Zlata A. Brushevich, Anton A. Muravev, Elad Nadav, Yael Tsarfati, Anna Kossoy, Isai Feldman, Anastasia Zelenina, Anna A. Rubekina, Sergey N. Semenov, Ekaterina V. Skorb. Altering the structures of 3D supramolecular assemblies from melamine and cyanuric acid derivatives in water. Chemical Communications 2024, 60 (77) , 10680-10683. https://doi.org/10.1039/D4CC02817A
    38. Lázaro A. M. Castanedo, Chérif F. Matta. Prebiotic N-(2-Aminoethyl)-Glycine (AEG)-Assisted Synthesis of Proto-RNA?. Journal of Molecular Evolution 2024, 92 (4) , 449-466. https://doi.org/10.1007/s00239-024-10185-w
    39. Wuxia Zhang, Yupeng Chen. Self-assembled Janus base nanotubes: chemistry and applications. Frontiers in Chemistry 2024, 11 https://doi.org/10.3389/fchem.2023.1346014
    40. Mattanjah S. de Vries, Nathan Svadlenak. Nucleobases as Molecular Fossils of Prebiotic Photoselection. 2024, 77-97. https://doi.org/10.1007/978-3-031-68807-2_4
    41. Liam F. McGarry, Osama El-Zubir, Paul G. Waddell, Fabio Cucinotta, Andrew Houlton, Benjamin R. Horrocks. Vesicles, fibres, films and crystals: A low-molecular-weight-gelator [Au(6-thioguanosine) 2 ]Cl which exhibits a co-operative anion-induced transition from vesicles to a fibrous metallo-hydrogel. Soft Matter 2023, 19 (43) , 8386-8402. https://doi.org/10.1039/D3SM01006F
    42. Sk Nurul Hasan, Jhimli Banerjee, Soumen Patra, Sukhendu Kar, Sayan Das, Sovan Samanta, Dharani Wanigasekera, Upekshi Pavithra, Kanchana Wijesekera, Mayuri Napagoda, Biplab Giri, Sandeep Kumar Dash, Braja Gopal Bag. Self-assembled renewable nano-sized pentacyclic triterpenoid maslinic acids in aqueous medium for anti-leukemic, antibacterial and biocompatibility studies: An insight into targeted proteins-compound interactions based mechanistic pathway prediction through molecular docking. International Journal of Biological Macromolecules 2023, 245 , 125416. https://doi.org/10.1016/j.ijbiomac.2023.125416
    43. Ruslan Kashapov, Yuliya Razuvayeva, Nadezda Kashapova, Albina Ziganshina, Vadim Salnikov, Anastasiia Sapunova, Alexandra Voloshina, Lucia Zakharova. Emergence of Nanoscale Drug Carriers through Supramolecular Self-Assembly of RNA with Calixarene. International Journal of Molecular Sciences 2023, 24 (9) , 7911. https://doi.org/10.3390/ijms24097911
    44. Maryam Farzan, Alfred Ross, Claudia Müller, Andrea Allmendinger. Liquid crystal phase formation and non-Newtonian behavior of oligonucleotide formulations. European Journal of Pharmaceutics and Biopharmaceutics 2022, 181 , 270-281. https://doi.org/10.1016/j.ejpb.2022.11.021
    45. Cristina Pérez-Fernández, Jorge Vega, Pedro Rayo-Pizarroso, Eva Mateo-Marti, Marta Ruiz-Bermejo. Prebiotic synthesis of noncanonical nucleobases under plausible alkaline hydrothermal conditions. Scientific Reports 2022, 12 (1) https://doi.org/10.1038/s41598-022-19474-0
    46. Vivekanand Shukla, Yang Jiao, Jung-Hoon Lee, Elsebeth Schröder, Jeffrey B. Neaton, Per Hyldgaard. Accurate Nonempirical Range-Separated Hybrid van der Waals Density Functional for Complex Molecular Problems, Solids, and Surfaces. Physical Review X 2022, 12 (4) https://doi.org/10.1103/PhysRevX.12.041003
    47. Jingjing Yu, Dawei Qi, Ermei Mäkilä, Lippo Lassila, Anastassios C. Papageorgiou, Markus Peurla, Jessica M. Rosenholm, Zhao Zhao, Pekka Vallittu, Sirpa Jalkanen, Chunman Jia, Jianwei Li. Small‐Molecule‐based Supramolecular Plastics Mediated by Liquid‐Liquid Phase Separation**. Angewandte Chemie 2022, 134 (39) https://doi.org/10.1002/ange.202204611
    48. Jingjing Yu, Dawei Qi, Ermei Mäkilä, Lippo Lassila, Anastassios C. Papageorgiou, Markus Peurla, Jessica M. Rosenholm, Zhao Zhao, Pekka Vallittu, Sirpa Jalkanen, Chunman Jia, Jianwei Li. Small‐Molecule‐based Supramolecular Plastics Mediated by Liquid‐Liquid Phase Separation**. Angewandte Chemie International Edition 2022, 61 (39) https://doi.org/10.1002/anie.202204611
    49. Serge Nader, Lorenzo Sebastianelli, Sheref S. Mansy. Protometabolism as out-of-equilibrium chemistry. Philosophical Transactions of the Royal Society A: Mathematical, Physical and Engineering Sciences 2022, 380 (2227) https://doi.org/10.1098/rsta.2020.0423
    50. Andre Nicolai Petelski, Silvana Carina Pamies, María Josefina Verónica Márquez, Gladis Laura Sosa, Nélida María Peruchena. Impact of Covalent Modifications on the Hydrogen Bond Strengths in Diaminotriazine Supramolecules. ChemPhysChem 2022, 23 (13) https://doi.org/10.1002/cphc.202200151
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    52. Carina Lee, Jessica Weber, Laura Rodriguez, Rachel Sheppard, Laura Barge, Eve Berger, Aaron Burton. Chirality in Organic and Mineral Systems: A Review of Reactivity and Alteration Processes Relevant to Prebiotic Chemistry and Life Detection Missions. Symmetry 2022, 14 (3) , 460. https://doi.org/10.3390/sym14030460
    53. Luis A. Ortiz-Rodríguez, Sean J. Hoehn, Carlos E. Crespo-Hernández. On the Photostability of Cyanuric Acid and Its Candidature as a Prebiotic Nucleobase. Molecules 2022, 27 (4) , 1184. https://doi.org/10.3390/molecules27041184
    54. Han-Xiao Wang, Lifei Xu, Xuefeng Zhu, Chenlu Xue, Li Zhang, Minghua Liu. Dissymmetrical tails-regulated helical nanoarchitectonics of amphiphilic ornithines: nanotubes, bundles and twists. Nanoscale 2022, 14 (3) , 1001-1007. https://doi.org/10.1039/D1NR07538A
    55. Monica-Cornelia Sardaru, Irina Rosca, Simona Morariu, Elena-Laura Ursu, Razvan Ghiarasim, Alexandru Rotaru. Injectable Thixotropic β–Cyclodextrin–Functionalized Hydrogels Based on Guanosine Quartet Assembly. International Journal of Molecular Sciences 2021, 22 (17) , 9179. https://doi.org/10.3390/ijms22179179
    56. Edgard G. Rivera-Valentín, Justin Filiberto, Kennda L. Lynch, Irena Mamajanov, Timothy W. Lyons, Mitch Schulte, Abel Méndez. Introduction—First Billion Years: Habitability. Astrobiology 2021, 21 (8) , 893-905. https://doi.org/10.1089/ast.2020.2314
    57. Asem Alenaizan, Kévin Fauché, Ramanarayanan Krishnamurthy, C. David Sherrill. Noncovalent Helicene Structure between Nucleic Acids and Cyanuric Acid. Chemistry – A European Journal 2021, 27 (12) , 4043-4052. https://doi.org/10.1002/chem.202004390
    58. Brooke A. Anderson, Kévin Fauché, Suneesh C. Karunakaran, Jayasudhan R. Yerabolu, Nicholas V. Hud, Ramanarayanan Krishnamurthy. The Unexpected Base‐Pairing Behavior of Cyanuric Acid in RNA and Ribose versus Cyanuric Acid Induced Helicene Assembly of Nucleic Acids: Implications for the Pre‐RNA Paradigm. Chemistry – A European Journal 2021, 27 (12) , 4033-4042. https://doi.org/10.1002/chem.202004397
    59. Conor D. Rankine. Ultrafast excited-state dynamics of promising nucleobase ancestor 2,4,6-triaminopyrimidine. Physical Chemistry Chemical Physics 2021, 23 (6) , 4007-4017. https://doi.org/10.1039/D0CP05609J
    60. Asem Alenaizan, Joshua L Barnett, Nicholas V Hud, C David Sherrill, Anton S Petrov. The proto-Nucleic Acid Builder: a software tool for constructing nucleic acid analogs. Nucleic Acids Research 2021, 49 (1) , 79-89. https://doi.org/10.1093/nar/gkaa1159
    61. Mengfan Wu, Chuyan Zhang, Fujing Wei, Huifang An, Xiaqing Wang, Dan Li, Haoyu Wang, Kexiong Wen, Qingyu Lin, Yixiang Duan. A self-assembly based on a hydrogel interface: facile, rapid, and large-scale preparation of colloidal photonic crystals. Materials Chemistry Frontiers 2020, 4 (8) , 2409-2417. https://doi.org/10.1039/D0QM00266F
    62. Maximino Aldana, Miguel Fuentes-Cabrera, Martín Zumaya. Self-Propulsion Enhances Polymerization. Entropy 2020, 22 (2) , 251. https://doi.org/10.3390/e22020251
    63. Kelly G. Aukema, Lambros J. Tassoulas, Serina L. Robinson, Jessica F. Konopatski, Madison D. Bygd, Lawrence P. Wackett, . Cyanuric Acid Biodegradation via Biuret: Physiology, Taxonomy, and Geospatial Distribution. Applied and Environmental Microbiology 2020, 86 (2) https://doi.org/10.1128/AEM.01964-19
    64. Songjun Xiao, Paul J. Paukstelis, Richard D. Ash, Peter Y. Zavalij, Jeffery T. Davis. Drawing with Iron on a Gel Containing a Supramolecular Siderophore. Angewandte Chemie 2019, 131 (51) , 18605-18608. https://doi.org/10.1002/ange.201910872
    65. Songjun Xiao, Paul J. Paukstelis, Richard D. Ash, Peter Y. Zavalij, Jeffery T. Davis. Drawing with Iron on a Gel Containing a Supramolecular Siderophore. Angewandte Chemie International Edition 2019, 58 (51) , 18434-18437. https://doi.org/10.1002/anie.201910872
    66. Laura E. Rodriguez, Christopher H. House, Karen E. Smith, Melissa R. Roberts, Michael P. Callahan. Nitrogen heterocycles form peptide nucleic acid precursors in complex prebiotic mixtures. Scientific Reports 2019, 9 (1) https://doi.org/10.1038/s41598-019-45310-z
    67. Sarabjeet Kaur, Purshotam Sharma. Radical pathways for the formation of non-canonical nucleobases in prebiotic environments. RSC Advances 2019, 9 (63) , 36530-36538. https://doi.org/10.1039/C9RA08001E
    68. Gregory Gate, Rafał Szabla, Michael R. Haggmark, Jiří Šponer, Andrzej L. Sobolewski, Mattanjah S. de Vries. Photodynamics of alternative DNA base isoguanine. Physical Chemistry Chemical Physics 2019, 21 (25) , 13474-13485. https://doi.org/10.1039/C9CP01622H
    69. Rie Wakabayashi, Hiroki Obayashi, Ryuichiro Hashimoto, Noriho Kamiya, Masahiro Goto. Complementary interaction with peptide amphiphiles guides size-controlled assembly of small molecules for intracellular delivery. Chemical Communications 2019, 55 (49) , 6997-7000. https://doi.org/10.1039/C9CC02473E
    70. Petr Motloch, Ana Guerreiro, Carolina Q. Azeredo, Gonçalo J. L. Bernardes, Christopher A. Hunter, Istvan Kocsis. Triaminopyrimidine derivatives as transmembrane HCl transporters. Organic & Biomolecular Chemistry 2019, 17 (22) , 5633-5638. https://doi.org/10.1039/C9OB00725C
    71. Sarabjeet Kaur, Purshotam Sharma, Stacey D. Wetmore. Can Cyanuric Acid and 2,4,6‐Triaminopyrimidine Containing Ribonucleosides be Components of Prebiotic RNA? Insights from QM Calculations and MD Simulations. ChemPhysChem 2019, 20 (11) , 1425-1436. https://doi.org/10.1002/cphc.201900237
    72. Aram Jeon, Jintaek Gong, Jun Kyun Oh, Sunbum Kwon, Wonchul Lee, Sang Ouk Kim, Sung June Cho, Hee‐Seung Lee. Spontaneous Nanobelt Formation by Self‐Assembly of β‐Benzyl GABA. Chemistry – An Asian Journal 2019, 14 (11) , 1945-1948. https://doi.org/10.1002/asia.201900363
    73. Andre Nicolai Petelski, Célia Fonseca Guerra. Designing Self‐Assembled Rosettes: Why Ammeline is a Superior Building Block to Melamine. ChemistryOpen 2019, 8 (2) , 135-142. https://doi.org/10.1002/open.201800210
    74. Suneesh C. Karunakaran, Brian J. Cafferty, Angela Weigert‐Muñoz, Gary B. Schuster, Nicholas V. Hud. Spontaneous Symmetry Breaking in the Formation of Supramolecular Polymers: Implications for the Origin of Biological Homochirality. Angewandte Chemie 2019, 131 (5) , 1467-1471. https://doi.org/10.1002/ange.201812808
    75. Suneesh C. Karunakaran, Brian J. Cafferty, Angela Weigert‐Muñoz, Gary B. Schuster, Nicholas V. Hud. Spontaneous Symmetry Breaking in the Formation of Supramolecular Polymers: Implications for the Origin of Biological Homochirality. Angewandte Chemie International Edition 2019, 58 (5) , 1453-1457. https://doi.org/10.1002/anie.201812808
    76. Bisang Chen, Feiming Li, Liling Zou, Dejian Chen. Intermolecular hydrogen bonding-mediated synthesis of high-quality photoluminescent carbon dots for label-free fluorometric detection of Fe3+ ions. Journal of Colloid and Interface Science 2019, 534 , 381-388. https://doi.org/10.1016/j.jcis.2018.09.050
    77. Suneesh C. Karunakaran, Brian J. Cafferty, Miguel Peláez-Fernández, Kasahun Neselu, Ingeborg Schmidt-Krey, Alberto Fernandez-Nieves, Gary B. Schuster, Nicholas V. Hud. Exquisite regulation of supramolecular equilibrium polymers in water: chain stoppers control length, polydispersity and viscoelasticity. Polymer Chemistry 2018, 9 (43) , 5268-5277. https://doi.org/10.1039/C8PY01146J
    78. Joaquín Calbo. Supramolecular polymer chemistry meets computational chemistry: theoretical simulations on advanced self-assembling chiral materials. Supramolecular Chemistry 2018, 30 (10) , 876-890. https://doi.org/10.1080/10610278.2018.1432860
    79. Ravi Joshi. Free radical induced redox reactions of 2,4,6-triaminopyrimidine: A pulse radiolysis study. Radiation Physics and Chemistry 2018, 151 , 169-178. https://doi.org/10.1016/j.radphyschem.2018.06.004
    80. Yan Xiao, Jiaxiao Zhang, Meidong Lang. Melamine driven supramolecular self‐assembly of nucleobase derivatives in water. Journal of Polymer Science Part A: Polymer Chemistry 2018, 56 (7) , 789-796. https://doi.org/10.1002/pola.28954
    81. Brian J. Cafferty, David M. Fialho, Nicholas V. Hud. Searching for Possible Ancestors of RNA: The Self-Assembly Hypothesis for the Origin of Proto-RNA. 2018, 143-174. https://doi.org/10.1007/978-3-319-93584-3_5
    82. Isaac Gállego, Christine He. Template-Directed Replication of Nucleic Acids Mediated by Viscous Environments. 2018, 199-225. https://doi.org/10.1007/978-3-319-93584-3_7
    83. Deiaa M. Harraz, Jeffery T. Davis. A self-assembled peroxidase from 5′-GMP and heme. Chemical Communications 2018, 54 (13) , 1587-1590. https://doi.org/10.1039/C7CC09900B
    84. David M. Fialho, Kimberly C. Clarke, Megan K. Moore, Gary B. Schuster, Ramanarayanan Krishnamurthy, Nicholas V. Hud. Glycosylation of a model proto-RNA nucleobase with non-ribose sugars: implications for the prebiotic synthesis of nucleosides. Organic & Biomolecular Chemistry 2018, 16 (8) , 1263-1271. https://doi.org/10.1039/C7OB03017G
    85. Federica Carducci, Juliana S. Yoneda, Rosangela Itri, Paolo Mariani. On the structural stability of guanosine-based supramolecular hydrogels. Soft Matter 2018, 14 (15) , 2938-2948. https://doi.org/10.1039/C8SM00299A
    86. Sandeepa Kulala Vittala, Sajena Kanangat Saraswathi, Joshy Joseph. Fullerene Cluster Assisted Self‐Assembly of Short DNA Strands into Semiconducting Nanowires. Chemistry – A European Journal 2017, 23 (62) , 15759-15765. https://doi.org/10.1002/chem.201703333
    87. Sarah A. Lundell, Alexandra M. Brown, Anthony M. Santora, Steven M. Romanelli, Ipsita A. Banerjee. Development of Self-Assembled Gold Nanoparticle Bound Amino Hydroxy Mercaptopurine Hybrids as Sensors for DNA Binding. Nano Hybrids and Composites 2017, 18 , 20-33. https://doi.org/10.4028/www.scientific.net/NHC.18.20
    88. Jan Zidek, Eva Kulovana, Josef Jancar. The Effect of Network Solvation on the Viscoelastic Response of Polymer Hydrogels. Polymers 2017, 9 (8) , 379. https://doi.org/10.3390/polym9080379
    89. Karen E. Smith, Christopher H. House, Jason P. Dworkin, Michael P. Callahan. Spontaneous Oligomerization of Nucleotide Alternatives in Aqueous Solutions. Origins of Life and Evolution of Biospheres 2017, 47 (1) , 3-11. https://doi.org/10.1007/s11084-016-9484-3
    90. Pol Besenius. Controlling supramolecular polymerization through multicomponent self‐assembly. Journal of Polymer Science Part A: Polymer Chemistry 2017, 55 (1) , 34-78. https://doi.org/10.1002/pola.28385
    91. K. Kanagaraj, M. Alagesan, Y. Inoue, C. Yang. Solvation Effects in Supramolecular Chemistry. 2017, 11-60. https://doi.org/10.1016/B978-0-12-409547-2.12481-3
    92. F. Biedermann. Self-Assembly in Aqueous Media. 2017, 241-268. https://doi.org/10.1016/B978-0-12-409547-2.12487-4
    93. H. Fenniri, K.W. Temburnikar, R.S. Johnson. Rosettes: Self-Assembled Supermacrocycles. 2017, 83-113. https://doi.org/10.1016/B978-0-12-409547-2.12583-1
    94. Alexandru Rotaru, Gabriela Pricope, Taylor N. Plank, Lilia Clima, Elena L. Ursu, Mariana Pinteala, Jeffery T. Davis, Mihail Barboiu. G-Quartet hydrogels for effective cell growth applications. Chemical Communications 2017, 53 (94) , 12668-12671. https://doi.org/10.1039/C7CC07806D
    95. D. V. Andreeva, A. Kollath, N. Brezhneva, D. V. Sviridov, B. J. Cafferty, H. Möhwald, E. V. Skorb. Using a chitosan nanolayer as an efficient pH buffer to protect pH-sensitive supramolecular assemblies. Physical Chemistry Chemical Physics 2017, 19 (35) , 23843-23848. https://doi.org/10.1039/C7CP02618H
    96. Giulia Marafon, Ileana Menegazzo, Marta De Zotti, Marco Crisma, Claudio Toniolo, Alessandro Moretto. Tuning morphological architectures generated through living supramolecular assembly of a helical foldamer end-capped with two complementary nucleobases. Soft Matter 2017, 13 (23) , 4231-4240. https://doi.org/10.1039/C7SM00764G
    97. Brian J. Cafferty, David M. Fialho, Jaheda Khanam, Ramanarayanan Krishnamurthy, Nicholas V. Hud. Spontaneous formation and base pairing of plausible prebiotic nucleotides in water. Nature Communications 2016, 7 (1) https://doi.org/10.1038/ncomms11328
    98. Jessica A. M. Yeates, Christian Hilbe, Martin Zwick, Martin A. Nowak, Niles Lehman. Dynamics of prebiotic RNA reproduction illuminated by chemical game theory. Proceedings of the National Academy of Sciences 2016, 113 (18) , 5030-5035. https://doi.org/10.1073/pnas.1525273113
    99. Nicole Avakyan, Andrea A. Greschner, Faisal Aldaye, Christopher J. Serpell, Violeta Toader, Anne Petitjean, Hanadi F. Sleiman. Reprogramming the assembly of unmodified DNA with a small molecule. Nature Chemistry 2016, 8 (4) , 368-376. https://doi.org/10.1038/nchem.2451
    100. Jennifer L. Seffernick, Lawrence P. Wackett, . Ancient Evolution and Recent Evolution Converge for the Biodegradation of Cyanuric Acid and Related Triazines. Applied and Environmental Microbiology 2016, 82 (6) , 1638-1645. https://doi.org/10.1128/AEM.03594-15
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    Cite this: J. Am. Chem. Soc. 2013, 135, 7, 2447–2450
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