BIBLIOS

Tipo
Artigos em Revista

Tipo de Documento
Artigo Completo

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

Participantes na publicação
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)

Resumo
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.


Instituição
FACULDADE DE CIÊNCIAS DA UNIVERSIDADE DE LISBOA

Suporte
CHEMISTRY-A EUROPEAN JOURNAL

Identificadores da Publicação
ISSN - 0947-6539

Editora
Wiley



Identificadores do Documento
URL - http://dx.doi.org/10.1002/chem.201501249
DOI - https://doi.org/10.1002/chem.201501249

Identificadores de Qualidade
Web Of Science Q1 (2018) - 5.160 - Chemistry, Multidisciplinary

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