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Revisiting the planarity of nucleic acid bases: Pyramidilization at glycosidic nitrogen in purine bases is modulated by orientation of glycosidic torsion

We describe a novel, fundamental property of nucleobase structure, namely, pyramidilization at the N1/9 sites of purine and pyrimidine bases. Through a combined analyses of ultra-high-resolution X-ray structures of both oligonucleotides extracted from the Nucleic Acid Database and isolated nucleotid...

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Autores principales: Sychrovsky, Vladimir, Foldynova-Trantirkova, Silvie, Spackova, Nada, Robeyns, Koen, Van Meervelt, Luc, Blankenfeldt, Wulf, Vokacova, Zuzana, Sponer, Jiri, Trantirek, Lukas
Formato: Texto
Lenguaje:English
Publicado: Oxford University Press 2009
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2790901/
https://www.ncbi.nlm.nih.gov/pubmed/19786496
http://dx.doi.org/10.1093/nar/gkp783
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author Sychrovsky, Vladimir
Foldynova-Trantirkova, Silvie
Spackova, Nada
Robeyns, Koen
Van Meervelt, Luc
Blankenfeldt, Wulf
Vokacova, Zuzana
Sponer, Jiri
Trantirek, Lukas
author_facet Sychrovsky, Vladimir
Foldynova-Trantirkova, Silvie
Spackova, Nada
Robeyns, Koen
Van Meervelt, Luc
Blankenfeldt, Wulf
Vokacova, Zuzana
Sponer, Jiri
Trantirek, Lukas
author_sort Sychrovsky, Vladimir
collection PubMed
description We describe a novel, fundamental property of nucleobase structure, namely, pyramidilization at the N1/9 sites of purine and pyrimidine bases. Through a combined analyses of ultra-high-resolution X-ray structures of both oligonucleotides extracted from the Nucleic Acid Database and isolated nucleotides and nucleosides from the Cambridge Structural Database, together with a series of quantum chemical calculations, molecular dynamics (MD) simulations, and published solution nuclear magnetic resonance (NMR) data, we show that pyramidilization at the glycosidic nitrogen is an intrinsic property. This property is common to isolated nucleosides and nucleotides as well as oligonucleotides—it is also common to both RNA and DNA. Our analysis suggests that pyramidilization at N1/9 sites depends in a systematic way on the local structure of the nucleoside. Of note, the pyramidilization undergoes stereo-inversion upon reorientation of the glycosidic bond. The extent of the pyramidilization is further modulated by the conformation of the sugar ring. The observed pyramidilization is more pronounced for purine bases, while for pyrimidines it is negligible. We discuss how the assumption of nucleic acid base planarity can lead to systematic errors in determining the conformation of nucleotides from experimental data and from unconstrained MD simulations.
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spelling pubmed-27909012009-12-09 Revisiting the planarity of nucleic acid bases: Pyramidilization at glycosidic nitrogen in purine bases is modulated by orientation of glycosidic torsion Sychrovsky, Vladimir Foldynova-Trantirkova, Silvie Spackova, Nada Robeyns, Koen Van Meervelt, Luc Blankenfeldt, Wulf Vokacova, Zuzana Sponer, Jiri Trantirek, Lukas Nucleic Acids Res Structural Biology We describe a novel, fundamental property of nucleobase structure, namely, pyramidilization at the N1/9 sites of purine and pyrimidine bases. Through a combined analyses of ultra-high-resolution X-ray structures of both oligonucleotides extracted from the Nucleic Acid Database and isolated nucleotides and nucleosides from the Cambridge Structural Database, together with a series of quantum chemical calculations, molecular dynamics (MD) simulations, and published solution nuclear magnetic resonance (NMR) data, we show that pyramidilization at the glycosidic nitrogen is an intrinsic property. This property is common to isolated nucleosides and nucleotides as well as oligonucleotides—it is also common to both RNA and DNA. Our analysis suggests that pyramidilization at N1/9 sites depends in a systematic way on the local structure of the nucleoside. Of note, the pyramidilization undergoes stereo-inversion upon reorientation of the glycosidic bond. The extent of the pyramidilization is further modulated by the conformation of the sugar ring. The observed pyramidilization is more pronounced for purine bases, while for pyrimidines it is negligible. We discuss how the assumption of nucleic acid base planarity can lead to systematic errors in determining the conformation of nucleotides from experimental data and from unconstrained MD simulations. Oxford University Press 2009-11 2009-09-28 /pmc/articles/PMC2790901/ /pubmed/19786496 http://dx.doi.org/10.1093/nar/gkp783 Text en © The Author(s) 2009. Published by Oxford University Press. http://creativecommons.org/licenses/by-nc/2.5/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/2.5/uk/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Structural Biology
Sychrovsky, Vladimir
Foldynova-Trantirkova, Silvie
Spackova, Nada
Robeyns, Koen
Van Meervelt, Luc
Blankenfeldt, Wulf
Vokacova, Zuzana
Sponer, Jiri
Trantirek, Lukas
Revisiting the planarity of nucleic acid bases: Pyramidilization at glycosidic nitrogen in purine bases is modulated by orientation of glycosidic torsion
title Revisiting the planarity of nucleic acid bases: Pyramidilization at glycosidic nitrogen in purine bases is modulated by orientation of glycosidic torsion
title_full Revisiting the planarity of nucleic acid bases: Pyramidilization at glycosidic nitrogen in purine bases is modulated by orientation of glycosidic torsion
title_fullStr Revisiting the planarity of nucleic acid bases: Pyramidilization at glycosidic nitrogen in purine bases is modulated by orientation of glycosidic torsion
title_full_unstemmed Revisiting the planarity of nucleic acid bases: Pyramidilization at glycosidic nitrogen in purine bases is modulated by orientation of glycosidic torsion
title_short Revisiting the planarity of nucleic acid bases: Pyramidilization at glycosidic nitrogen in purine bases is modulated by orientation of glycosidic torsion
title_sort revisiting the planarity of nucleic acid bases: pyramidilization at glycosidic nitrogen in purine bases is modulated by orientation of glycosidic torsion
topic Structural Biology
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2790901/
https://www.ncbi.nlm.nih.gov/pubmed/19786496
http://dx.doi.org/10.1093/nar/gkp783
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