Conformational study of DNA sugars: From the gas phase to solution

Uriarte, Iciar

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https://hdl.handle.net/2142/96942 Copy

Description

Title

Conformational study of DNA sugars: From the gas phase to solution

Author(s)

Uriarte, Iciar

Contributor(s)

• Davis, Benjamin G.
• Corzana, Francisco
• Cocinero, Emilio J.
• Vallejo-López, Montserrat

Issue Date

2017-06-21

Keyword(s)

• Conformers
• Isomers
• Chirality
• Stereochemistry

Abstract

begin{wrapfigure}{r}{0pt}_x000d_ includegraphics[scale=0.25]{ribofuranose.eps}_x000d_ end{wrapfigure}_x000d_ _x000d_ Sugars are versatile molecules that play a variety of roles in the organism. For example, they are important in energy storage processes or as structural scaffolds. Here, we focus on the monosaccharide present in DNA by addressing the conformational and puckering properties in the gas phase of $alpha$- and mbox{$beta$-methyl-2-deoxy-ribofuranoside} and $alpha$- and $beta$-methyl-2-deoxy-ribopiranoside. Other sugars have been previously studied in the gas phasefootnote{E. J. Cocinero, A. Lesarri, P. Écija, F. J. Basterretxea, J.-U. Grabow, J. A. Fernández, F. Castaño, textit{Angew. Chem. Int. Edit.} 2012, textbf{51}, 3119.}$^{,}$footnote{P. Écija, I. Uriarte, L. Spada, B. G. Davis, W. Caminati, F. J. Basterretxea, A. Lesarri, E. J. Cocinero, textit{Chem. Commun.} 2016, textbf{52}, 6241.}._x000d_ _x000d_ The work presented here stems from a combination of chemical synthesis, ultrafast vaporization methods, supersonic expansions, microwave spectroscopy (both chirped-pulsed and Balle-Flygare cavity-based spectrometers) and NMR spectroscopy. Previous studies in the gas phase had been performed on mbox{2-deoxyribose}footnote{I. Peña, E. J. Cocinero, C. Cabezas, A. Lesarri, S. Mata, P. Écija, A. M. Daly, Á. Cimas, C. Bermúdez, F. J. Basterretxea, S. Blanco, J. A. Fernández, J. C. López, F. Castaño, J. L. Alonso, textit{Angew. Chem. Int. Edit.} 2013, textbf{52}, 11840.}, but only piranose forms were detected. However, thanks to the combination of these techniques, we have isolated and characterized for the first time the conformational landscape of the sugar present in DNA in its biologically relevant furanose form. Our gas phase study serves as a probe of the conformational preferences of these biomolecules under isolation conditions. Thanks to the NMR experiments, we can characterize the favored conformations in solution and extract the role of the solvent in the structure and puckering of the monosaccharides._x000d_

Publisher

International Symposium on Molecular Spectroscopy

Type of Resource

text

Language

eng

Permalink

http://hdl.handle.net/2142/96942

DOI

https://doi.org/10.15278/isms.2017.WC04

Copyright and License Information

Copyright 2017 Iciar Uriarte

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