University of Illinois Urbana-Champaign

Fluorination And Deoxygenation As Chemical Tools To Study The Conformational Preferences Of Hexopyranoses: A Journey From Gas Phase To Solution

Cocinero, Emilio J.

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WL03_1.pptx
6439.pdf

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https://hdl.handle.net/2142/116872

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Title
Fluorination And Deoxygenation As Chemical Tools To Study The Conformational Preferences Of Hexopyranoses: A Journey From Gas Phase To Solution
Author(s)
Cocinero, Emilio J.
Contributor(s)
  • Boutureira, Omar
  • Corzana, Francisco
  • Basterretxea, Francisco J.
  • Calabrese, Camilla
  • Insausti, Aran
  • Alonso, Elena R.
Issue Date
2022-06-22
Keyword(s)
Conformers and isomers
Abstract
\begin{wrapfigure}{l}{0pt} \includegraphics[scale=0.16]{Figura2.eps} \end{wrapfigure} The 3D-arrangement of carbohydrates and, particularly, the orientation of their hydroxymethyl groups are structural features crucial for their biological activities. In this work, we investigate the influence of water on the conformational preferences of model hexopyranoses by performing a comprehensive analysis in the gas phase via microwave spectroscopy\footnote{C. Calabrese, I. Uriarte, A. Insausti, M. Vallejo-Lopez, F. J. Basterretxea, S. A. Cochrane, B. G. Davis, F. Corzana and E. J. Cocinero \textit{ACS Cent. Sci.}, \textbf{6}, 293-303, 2020.}$^{,}$\footnote{E. J. Cocinero, A. Lesarri, P. Ecija, F. J. Basterretxea, J.-U. Grabow, J. A. Fernandez, F. Castaño \textit{Angew. Chem. Int. Ed.}, \textbf{51}, 3119, 2012.} of different fluorinated and deoxygenated carbohydrate analogues and comparing the results with those obtained in solution using a combination of NMR data and molecular dynamics simulations. The gg conformation is stabilized in the gas phase by intra molecular HBs that lock this conformation when oriented clockwise. However, and contrary to previously reported data, the conformation of the hydroxymethyl group in D-gluco and D-mannopyranose series follows a similar tendency in the gas phase and in solution, indicating the importance of stereo electronic and minimizing the importance of competing water molecules against stabilizing intra molecular HBs.
Publisher
International Symposium on Molecular Spectroscopy
Type of Resource
text
Genre of Resource
Conference Paper / Presentation
Language
eng
Handle URL
https://hdl.handle.net/2142/116872
DOI
https://doi.org/10.15278/isms.2022.WL03
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Copyright 2022 held by the authors

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Abstracts & Presentations - 2022 International Symposium on Molecular Spectroscopy PRIMARY