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首页> 外文期刊>Chemistry: A European journal >Conformational Plasticity in Glycomimetics: Fluorocarbamethyl-L-idopyranosides Mimic the Intrinsic Dynamic Behaviour of Natural Idose Rings
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Conformational Plasticity in Glycomimetics: Fluorocarbamethyl-L-idopyranosides Mimic the Intrinsic Dynamic Behaviour of Natural Idose Rings

机译：糖代谢的构象可塑性：氟碳甲基-L-idopyranosides模仿天然的同剂量环的内在动力学行为。

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摘要

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.
机译：糖的功能，结构和动力学有着复杂的联系。环的柔韧性本质上与生物活性有关。实际上，L-艾杜糖环的可塑性调节了它们与生物受体的相互作用。然而，难以获得水溶液中构象异构体互变的能垒和自由能差的实验值。在此，提出了新一代的含氟糖模拟物。我们已经应用有机合成，核磁共振波谱和计算方法的组合来研究象糖和葡萄糖样环的构象行为。我们已经使用了低温NMR光谱实验来减慢像糖一样的环的构象交换。在这些条件下，交换速率在（FNMR）-F-19光谱化学位移时间标度中变慢，并允许对平衡的热力学和动力学特征有所了解。尽管这些化合物之间的结构差异很小，但它们的动态行为确实存在显着差异。还强调了在这些糖模拟物中引入氟原子的重要性。只有（FNMR）-F-19光谱实验的使用才允许揭示构象平衡的关键特征，而这些特征本来就不会被观察到。

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