Strengthened cooperativity of DNA-based cyclic hydrogen-bonded rosettes by subtle functionalization

David Almacellas; Célia Fonseca Guerra; Jordi Poater

doi:10.1039/d3ob01391j

Strengthened cooperativity of DNA-based cyclic hydrogen-bonded rosettes by subtle functionalization

David Almacellas
, Célia Fonseca Guerra^*
, Jordi Poater^*

^*Corresponding author for this work

Research output: Contribution to Journal › Article › Academic › peer-review

Abstract

Cooperative effects cause extra stabilization of hydrogen-bonded supramolecular systems. In this work we have designed hydrogen-bonded rosettes derived from a guanine-cytosine Janus-type motif with the aim of finding a monomer that enhances the synergy of supramolecular systems. For this, relativistic dispersion-corrected density functional theory computations have been performed. Our proposal involves a monomer with three hydrogen-bonds pointing in the same direction, which translates into shorter bonds, stronger donor-acceptor interactions, and more attractive electrostatic interactions, thus giving rise to rosettes with strengthened cooperativity. This newly designed rosette has triple the cooperativity found for the naturally occurring guanine quadruplex.

Original language	English
Pages (from-to)	8403-8412
Number of pages	10
Journal	Organic and Biomolecular Chemistry
Volume	21
Issue number	41
Early online date	5 Oct 2023
DOIs	https://doi.org/10.1039/d3ob01391j
Publication status	Published - 7 Nov 2023

Bibliographical note

Funding Information:
We thank the Netherlands Organization for Scientific Research (NWO), the Spanish MINECO (PID-2019-106830GB-I00, PID2022-138861NB-I00 and CEX2021-001202-M) and the Catalan Government (2021SGR442) for financial support.

Publisher Copyright:
© 2023 The Royal Society of Chemistry

Funding

We thank the Netherlands Organization for Scientific Research (NWO), the Spanish MINECO (PID-2019-106830GB-I00, PID2022-138861NB-I00 and CEX2021-001202-M) and the Catalan Government (2021SGR442) for financial support.

Funders	Funder number
Generalitat de Catalunya	2021SGR442
Generalitat de Catalunya
Nederlandse Organisatie voor Wetenschappelijk Onderzoek
Ministerio de Economía y Competitividad	CEX2021-001202-M, PID-2019-106830GB-I00, PID2022-138861NB-I00
Ministerio de Economía y Competitividad

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title = "Strengthened cooperativity of DNA-based cyclic hydrogen-bonded rosettes by subtle functionalization",

abstract = "Cooperative effects cause extra stabilization of hydrogen-bonded supramolecular systems. In this work we have designed hydrogen-bonded rosettes derived from a guanine-cytosine Janus-type motif with the aim of finding a monomer that enhances the synergy of supramolecular systems. For this, relativistic dispersion-corrected density functional theory computations have been performed. Our proposal involves a monomer with three hydrogen-bonds pointing in the same direction, which translates into shorter bonds, stronger donor-acceptor interactions, and more attractive electrostatic interactions, thus giving rise to rosettes with strengthened cooperativity. This newly designed rosette has triple the cooperativity found for the naturally occurring guanine quadruplex.",

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AU - Almacellas, David

AU - Fonseca Guerra, Célia

AU - Poater, Jordi

N1 - Funding Information: We thank the Netherlands Organization for Scientific Research (NWO), the Spanish MINECO (PID-2019-106830GB-I00, PID2022-138861NB-I00 and CEX2021-001202-M) and the Catalan Government (2021SGR442) for financial support. Publisher Copyright: © 2023 The Royal Society of Chemistry

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N2 - Cooperative effects cause extra stabilization of hydrogen-bonded supramolecular systems. In this work we have designed hydrogen-bonded rosettes derived from a guanine-cytosine Janus-type motif with the aim of finding a monomer that enhances the synergy of supramolecular systems. For this, relativistic dispersion-corrected density functional theory computations have been performed. Our proposal involves a monomer with three hydrogen-bonds pointing in the same direction, which translates into shorter bonds, stronger donor-acceptor interactions, and more attractive electrostatic interactions, thus giving rise to rosettes with strengthened cooperativity. This newly designed rosette has triple the cooperativity found for the naturally occurring guanine quadruplex.

AB - Cooperative effects cause extra stabilization of hydrogen-bonded supramolecular systems. In this work we have designed hydrogen-bonded rosettes derived from a guanine-cytosine Janus-type motif with the aim of finding a monomer that enhances the synergy of supramolecular systems. For this, relativistic dispersion-corrected density functional theory computations have been performed. Our proposal involves a monomer with three hydrogen-bonds pointing in the same direction, which translates into shorter bonds, stronger donor-acceptor interactions, and more attractive electrostatic interactions, thus giving rise to rosettes with strengthened cooperativity. This newly designed rosette has triple the cooperativity found for the naturally occurring guanine quadruplex.

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Strengthened cooperativity of DNA-based cyclic hydrogen-bonded rosettes by subtle functionalization

Abstract

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