Cargando…
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...
Autores principales: | , , , |
---|---|
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 |
_version_ | 1785094169213009920 |
---|---|
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. |
format | Online Article Text |
id | pubmed-10445429 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT rosagastaldodaniele sequenceselectiveduplexformationandtemplateeffectinrecognitionencodedoligoanilines AT dallavalleandrea sequenceselectiveduplexformationandtemplateeffectinrecognitionencodedoligoanilines AT marchettitommaso sequenceselectiveduplexformationandtemplateeffectinrecognitionencodedoligoanilines AT gabrielliluca sequenceselectiveduplexformationandtemplateeffectinrecognitionencodedoligoanilines |