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Publication details

Document type
Journal articles

Document subtype
Full paper

Title
Conformational Plasticity in Glycomimetics: Fluorocarbamethyl-L-idopyranosides Mimic the Intrinsic Dynamic Behaviour of Natural Idose Rings

Participants in the publication
L. Unione (Author)
B. X. Xu (Author)
D. Diaz (Author)
S. Martin Santamaria (Author)
A. Poveda (Author)
J. Sardinha (Author)
A. P. Rauter (Author)
Dep. Química e Bioquímica
 CQB
 Y. Blériot (Author)
Y. M. Zhang (Author)
F. J. Cañada (Author)
M. Sollogoub (Author)
J. Jiménez-Barbero (Author)

Summary
Sugar function, structure and dynamics are intricately correlated. Ring flexibility is intrinsically related to biological activity; actually plasticity in L-iduronic rings modulates their interactions with biological receptors. However, the access to the experimental values of the energy barriers and free-energy difference for conformer interconversion in water solution has been elusive. Here, a new generation of fluorine-containing glycomimetics is presented. We have applied a combination of organic synthesis, NMR spectroscopy and computational methods to investigate the conformational behaviour of idose- and glucose-like rings. We have used low-temperature NMR spectroscopic experiments to slow down the conformational exchange of the idose-like rings. Under these conditions, the exchange rate becomes slow in the (FNMR)-F-19 spectroscopic chemical shift timescale and allows shedding light on the thermodynamic and kinetic features of the equilibrium. Despite the minimal structural differences between these compounds, a remarkable difference in their dynamic behaviour indeed occurs. The importance of introducing fluorine atoms in these sugars mimics is also highlighted. Only the use of (FNMR)-F-19 spectroscopic experiments has permitted the unveiling of key features of the conformational equilibrium that would have otherwise remained unobserved.

Date of Publication
2015

Institution
FACULDADE DE CIÊNCIAS DA UNIVERSIDADE DE LISBOA

Where published
CHEMISTRY-A EUROPEAN JOURNAL

Publication Identifiers
ISSN - 0947-6539

Publisher
Wiley

Volume
21
Number
29

Number of pages
9
Starting page
10513
Last page
10521

Document Identifiers
URL - http://dx.doi.org/10.1002/chem.201501249
DOI - https://doi.org/10.1002/chem.201501249

Rankings
Web Of Science Q1 (2018) - 5.160 - Chemistry, Multidisciplinary

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APA
L. Unione, B. X. Xu, D. Diaz, S. Martin Santamaria, A. Poveda, J. Sardinha, A. P. Rauter, Y. Blériot, Y. M. Zhang, F. J. Cañada, M. Sollogoub, J. Jiménez-Barbero, (2015). Conformational Plasticity in Glycomimetics: Fluorocarbamethyl-L-idopyranosides Mimic the Intrinsic Dynamic Behaviour of Natural Idose Rings . CHEMISTRY-A EUROPEAN JOURNAL, 21, 10513-10521. ISSN 0947-6539. eISSN . http://dx.doi.org/10.1002/chem.201501249

IEEE
L. Unione, B. X. Xu, D. Diaz, S. Martin Santamaria, A. Poveda, J. Sardinha, A. P. Rauter, Y. Blériot, Y. M. Zhang, F. J. Cañada, M. Sollogoub, J. Jiménez-Barbero, "Conformational Plasticity in Glycomimetics: Fluorocarbamethyl-L-idopyranosides Mimic the Intrinsic Dynamic Behaviour of Natural Idose Rings " in CHEMISTRY-A EUROPEAN JOURNAL, vol. 21, pp. 10513-10521, 2015. 10.1002/chem.201501249

BIBTEX
@article{26556, author = {L. Unione and B. X. Xu and D. Diaz and S. Martin Santamaria and A. Poveda and J. Sardinha and A. P. Rauter and Y. Blériot and Y. M. Zhang and F. J. Cañada and M. Sollogoub and J. Jiménez-Barbero}, title = {Conformational Plasticity in Glycomimetics: Fluorocarbamethyl-L-idopyranosides Mimic the Intrinsic Dynamic Behaviour of Natural Idose Rings }, journal = {CHEMISTRY-A EUROPEAN JOURNAL}, year = 2015, pages = {10513-10521}, volume = 21 }