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Sequence-selective duplex formation and template effect in recognition-encoded oligoanilines

A new family of duplex-forming recognition encoded oligomers, capable of sequence selective duplex formation and template directed synthesis, was developed. Monomers equipped with both amine and aldehyde groups were functionalized with 2-trifluoromethylphenol or phosphine oxide as H-bond recognition...

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Autores principales: Rosa-Gastaldo, Daniele, Dalla Valle, Andrea, Marchetti, Tommaso, Gabrielli, Luca
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10445429/
https://www.ncbi.nlm.nih.gov/pubmed/37621420
http://dx.doi.org/10.1039/d3sc00880k
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author Rosa-Gastaldo, Daniele
Dalla Valle, Andrea
Marchetti, Tommaso
Gabrielli, Luca
author_facet Rosa-Gastaldo, Daniele
Dalla Valle, Andrea
Marchetti, Tommaso
Gabrielli, Luca
author_sort Rosa-Gastaldo, Daniele
collection PubMed
description A new family of duplex-forming recognition encoded oligomers, capable of sequence selective duplex formation and template directed synthesis, was developed. Monomers equipped with both amine and aldehyde groups were functionalized with 2-trifluoromethylphenol or phosphine oxide as H-bond recognition units. Duplex formation and assembly properties of homo- and hetero-oligomers were studied by (19)F and (1)H NMR experiments in chloroform. The designed backbone prevents the undesired 1,2-folding allowing sequence-selective duplex formation, and the stability of the antiparallel duplex is 3-fold higher than the parallel arrangement. Dynamic combinatorial chemistry was exploited for the templated synthesis of complementary oligomers, showing that an aniline dimer can template the formation of the complementary imine. The key role of the H-bond recognition confers to the system the ability to discriminate a mutated donor monomer incapable of H-bonding. Sequence selective duplex formation combined with the template effect makes this system an attractive target for further studies.
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spelling pubmed-104454292023-08-24 Sequence-selective duplex formation and template effect in recognition-encoded oligoanilines Rosa-Gastaldo, Daniele Dalla Valle, Andrea Marchetti, Tommaso Gabrielli, Luca Chem Sci Chemistry A new family of duplex-forming recognition encoded oligomers, capable of sequence selective duplex formation and template directed synthesis, was developed. Monomers equipped with both amine and aldehyde groups were functionalized with 2-trifluoromethylphenol or phosphine oxide as H-bond recognition units. Duplex formation and assembly properties of homo- and hetero-oligomers were studied by (19)F and (1)H NMR experiments in chloroform. The designed backbone prevents the undesired 1,2-folding allowing sequence-selective duplex formation, and the stability of the antiparallel duplex is 3-fold higher than the parallel arrangement. Dynamic combinatorial chemistry was exploited for the templated synthesis of complementary oligomers, showing that an aniline dimer can template the formation of the complementary imine. The key role of the H-bond recognition confers to the system the ability to discriminate a mutated donor monomer incapable of H-bonding. Sequence selective duplex formation combined with the template effect makes this system an attractive target for further studies. The Royal Society of Chemistry 2023-07-26 /pmc/articles/PMC10445429/ /pubmed/37621420 http://dx.doi.org/10.1039/d3sc00880k Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Rosa-Gastaldo, Daniele
Dalla Valle, Andrea
Marchetti, Tommaso
Gabrielli, Luca
Sequence-selective duplex formation and template effect in recognition-encoded oligoanilines
title Sequence-selective duplex formation and template effect in recognition-encoded oligoanilines
title_full Sequence-selective duplex formation and template effect in recognition-encoded oligoanilines
title_fullStr Sequence-selective duplex formation and template effect in recognition-encoded oligoanilines
title_full_unstemmed Sequence-selective duplex formation and template effect in recognition-encoded oligoanilines
title_short Sequence-selective duplex formation and template effect in recognition-encoded oligoanilines
title_sort sequence-selective duplex formation and template effect in recognition-encoded oligoanilines
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10445429/
https://www.ncbi.nlm.nih.gov/pubmed/37621420
http://dx.doi.org/10.1039/d3sc00880k
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