Cargando…

On the stability of peptide nucleic acid duplexes in the presence of organic solvents

Nucleic acid double helices are stabilized by hydrogen bonding and stacking forces (a combination of hydrophobic, dispersive and electrostatic forces) of the base pairs in the helix. One would predict the hydrogen bonding contributions to increase and the stacking contributions to decrease as the wa...

Descripción completa

Detalles Bibliográficos
Autores principales: Sen, Anjana, Nielsen, Peter E.
Formato: Texto
Lenguaje:English
Publicado: Oxford University Press 2007
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1904262/
https://www.ncbi.nlm.nih.gov/pubmed/17478520
http://dx.doi.org/10.1093/nar/gkm210
_version_ 1782133983547490304
author Sen, Anjana
Nielsen, Peter E.
author_facet Sen, Anjana
Nielsen, Peter E.
author_sort Sen, Anjana
collection PubMed
description Nucleic acid double helices are stabilized by hydrogen bonding and stacking forces (a combination of hydrophobic, dispersive and electrostatic forces) of the base pairs in the helix. One would predict the hydrogen bonding contributions to increase and the stacking contributions to decrease as the water activity in the medium decreases. Study of nucleobase paired duplexes in the absence of water and ultimately in pure aprotic, non-polar organic solvents is not possible with natural phosphodiester nucleic acids due to the ionic phosphate groups and the associated cations, but could be possible with non-ionic nucleic acid analogues or mimics such as peptide nucleic acids. We now report that peptide nucleic acid (PNA) (in contrast to DNA) duplexes show almost unaffected stability in up to 70% dimethylformamide (DMF) or dioxane, and extrapolation of the data to conditions of 100% organic solvents indicates only minor (or no) destabilization of the PNA duplexes. Our data indicate that stacking forces contribute little if at all to the duplex stability under these conditions. The differences in behaviour between the PNA and the DNA duplexes are attributed to the differences in hydration and counter ion release rather than to the differences in nucleobase interaction. These results support the possibility of having stable nucleobase paired double helices in organic solvents.
format Text
id pubmed-1904262
institution National Center for Biotechnology Information
language English
publishDate 2007
publisher Oxford University Press
record_format MEDLINE/PubMed
spelling pubmed-19042622007-07-03 On the stability of peptide nucleic acid duplexes in the presence of organic solvents Sen, Anjana Nielsen, Peter E. Nucleic Acids Res Chemistry Nucleic acid double helices are stabilized by hydrogen bonding and stacking forces (a combination of hydrophobic, dispersive and electrostatic forces) of the base pairs in the helix. One would predict the hydrogen bonding contributions to increase and the stacking contributions to decrease as the water activity in the medium decreases. Study of nucleobase paired duplexes in the absence of water and ultimately in pure aprotic, non-polar organic solvents is not possible with natural phosphodiester nucleic acids due to the ionic phosphate groups and the associated cations, but could be possible with non-ionic nucleic acid analogues or mimics such as peptide nucleic acids. We now report that peptide nucleic acid (PNA) (in contrast to DNA) duplexes show almost unaffected stability in up to 70% dimethylformamide (DMF) or dioxane, and extrapolation of the data to conditions of 100% organic solvents indicates only minor (or no) destabilization of the PNA duplexes. Our data indicate that stacking forces contribute little if at all to the duplex stability under these conditions. The differences in behaviour between the PNA and the DNA duplexes are attributed to the differences in hydration and counter ion release rather than to the differences in nucleobase interaction. These results support the possibility of having stable nucleobase paired double helices in organic solvents. Oxford University Press 2007-05 2007-05-03 /pmc/articles/PMC1904262/ /pubmed/17478520 http://dx.doi.org/10.1093/nar/gkm210 Text en © 2007 The Author(s) http://creativecommons.org/licenses/by-nc/2.0/uk/ This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/2.0/uk/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Sen, Anjana
Nielsen, Peter E.
On the stability of peptide nucleic acid duplexes in the presence of organic solvents
title On the stability of peptide nucleic acid duplexes in the presence of organic solvents
title_full On the stability of peptide nucleic acid duplexes in the presence of organic solvents
title_fullStr On the stability of peptide nucleic acid duplexes in the presence of organic solvents
title_full_unstemmed On the stability of peptide nucleic acid duplexes in the presence of organic solvents
title_short On the stability of peptide nucleic acid duplexes in the presence of organic solvents
title_sort on the stability of peptide nucleic acid duplexes in the presence of organic solvents
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1904262/
https://www.ncbi.nlm.nih.gov/pubmed/17478520
http://dx.doi.org/10.1093/nar/gkm210
work_keys_str_mv AT senanjana onthestabilityofpeptidenucleicacidduplexesinthepresenceoforganicsolvents
AT nielsenpetere onthestabilityofpeptidenucleicacidduplexesinthepresenceoforganicsolvents