ArticleChemical science2017
Homochiral oligomers with highly flexible backbones form stable H-bonded duplexes.
Article in Chemical science, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed.
- Recognition-Encoded Molecules: A Minimal Self-Replicator.Chemistry (Weinheim an der Bergstrasse, Germany) · 2024Article
- Sequence-selective duplex formation and template effect in recognition-encoded oligoanilines.Chemical science · 2023Article
- Iridium-Catalyzed Synthesis of Chiral 1,2,3-Triazoles Units and Precise Construction of Stereocontrolled Oligomers.Molecules (Basel, Switzerland) · 2023Article
- Recognition-Encoded Synthetic Information Molecules.Accounts of chemical research · 2023Article
- H-Bond Templated Oligomer Synthesis Using a Covalent Primer.Journal of the American Chemical Society · 2022Article
- Folding and duplex formation in mixed sequence recognition-encodedChemical science · 2021Article
- High-Fidelity Sequence-Selective Duplex Formation by Recognition-Encoded Melamine Oligomers.Journal of the American Chemical Society · 2021Article
- Applications of Discrete Synthetic Macromolecules in Life and Materials Science: Recent and Future Trends.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2021Review
- Supramolecular catalysis by recognition-encoded oligomers: discovery of a synthetic imine polymerase.Chemical science · 2020Article
- Organogelating and narcissistic self-sorting behaviour of non-preorganized oligoamides.Chemical science · 2019Article
- Building blocks for recognition-encoded oligoesters that form H-bonded duplexes.Chemical science · 2019Article
- H-Bonded Duplexes based on a Phenylacetylene Backbone.Journal of the American Chemical Society · 2018Article
- Backbone conformation affects duplex initiation and duplex propagation in hybridisation of synthetic H-bonding oligomers.Organic & biomolecular chemistry · 2018Article
- Sequence-Selective Formation of Synthetic H-Bonded Duplexes.Journal of the American Chemical Society · 2017Article
- H-Bond Self-Assembly: Folding versus Duplex Formation.Journal of the American Chemical Society · 2017Article
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2 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Two homochiral building blocks featuring a protected thiol, an alkene and a H-bond recognition unit (phenol or phosphine oxide) have been prepared. Iterative photochemical thiol-ene coupling reactions were used to synthesize oligomers containing 1-4 phosphine oxide and 1-4 phenol recognition sites. Length-complementary H-bond donor and H-bond acceptor oligomers were found to form stable duplexes in toluene. NMR titrations and thermal denaturation experiments show that the association constant and the enthalpy of duplex formation increase significantly for every additional H-bonding unit added to the chain. There is an order of magnitude increase in stability for each additional H-bonding interaction at room temperature indicating that all of the H-bonding sites are fully bound to their complements in the duplexes. The backbone of the thiol-ene duplexes is a highly flexible alkane chain, but this conformational flexibility does not have a negative impact on binding affinity. The average effective molarity for the intramolecular H-bonding interactions that zip up the duplexes is 18 mM. This value is somewhat higher than the EM of 14 mM found for a related family of duplexes, which have the same recognition units but a more rigid backbone prepared using reductive amination chemistry. The flexible thiol-ene AAAA·DDDD duplex is an order of magnitude more stable than the rigid reductive amination AAAA·DDDD duplex. The backbone of the thiol-ene system retains much of its conformational flexibility in the duplex, and these results show that highly flexible molecules can make very stable complexes, provided there is no significant restriction of degrees of freedom on complexation.
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