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首页> 外文期刊>Chemistry: A European journal >Fluoroacetamide Moieties as NMR Spectroscopy Probes for the Molecular Recognition of GlcNAc-Containing Sugars: Modulation of the CH-π Stacking Interactions by Different Fluorination Patterns
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Fluoroacetamide Moieties as NMR Spectroscopy Probes for the Molecular Recognition of GlcNAc-Containing Sugars: Modulation of the CH-π Stacking Interactions by Different Fluorination Patterns

机译：氟乙酰胺部分作为NMR光谱探针，用于含GLCNAC糖的分子识别：通过不同氟化图案的CH-π堆叠相互作用的调制

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摘要

We herein propose the use of fluoroacetamide and difluoroacetamide moieties as sensitive tags for the detection of sugar-protein interactions by simple ~1H and/or ~(19)F NMR spectroscopy methods. In this process, we have chosen the binding of N,N'-diacetyl chitobiose, a ubiquitous disaccharide fragment in glycoproteins, by wheat-germ agglutinin (WGA), a model lectin. By using saturation-transfer difference (STD)-NMR spectroscopy, we experimentally demonstrate that, under solution conditions, the molecule that contained the CHF_2CONH- moiety is the stronger aromatic binder, followed by the analogue with the CH_2FCONHgroup and the natural molecule (with the CH_3CONH- fragment). In contrast, the molecule with the CF_3CONH- isoster displayed the weakest intermolecular interaction (one order of magnitude weaker). Because sugar-aromatic CH-π interactions are at the origin of these observations, these results further contribute to the characterization and exploration of these forces and offer an opportunity to use them to unravel complex recognition processes.
机译：我们在此提出使用氟乙酰胺和二氟乙酰胺部分作为敏感标签，用于通过简单〜1H和/或〜（19）F NMR光谱方法检测糖蛋白相互作用。在该方法中，我们选择了N，N'-二乙酰氧化甘油，糖蛋白（WGA）的糖蛋白（WGA），凝集素的结合。通过使用饱和转移差（STD）-NMR光谱学，我们通过实验证明，在溶液条件下，含有CHF_2CONH-部分的分子是更强的芳族粘合剂，其次是与CH_2FCONHGROUP和天然分子的类似物（用） ch_3conh-片段）。相反，具有CF_3CONH-的分子显示最弱的分子间相互作用（较小的一个数量级）。因为甘蔗芳族Ch-π相互作用处于这些观察结果的起源，因此这些结果进一步有助于这些力的表征和探索，并提供了将它们用来解析复杂识别过程的机会。

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  • 来源
    《Chemistry: A European journal》 |2017年第16期|共9页
  • 作者

    Luca Unione; Maria Alcalá; Bego?a Echeverria; Sonia Serna; Ana Ardá; Antonio Franconetti; F. Javier Ca?ada; Tammo Diercks; Niels Reichardt; Jesús Jiménez-Barbero;

  • 作者单位

    Molecular Recognition and Host-Pathogen Interactions CIC bioGUNE Bizkaia Technology Park Building 801 A 48170 Derio (Spain);

    Glycotechnology Laboratory CICbiomaGUNE Paseo Miramjn 20014 Donostia-San Sebastian (Spain);

    Glycotechnology Laboratory CICbiomaGUNE Paseo Miramjn 20014 Donostia-San Sebastian (Spain);

    Glycotechnology Laboratory CICbiomaGUNE Paseo Miramjn 20014 Donostia-San Sebastian (Spain);

    Molecular Recognition and Host-Pathogen Interactions CIC bioGUNE Bizkaia Technology Park Building 801 A 48170 Derio (Spain);

    Department of Organic Chemistry Faculty of Chemistry University of Seville Profesor García González 1 41012 Sevilla (Spain);

    Department of Chemical and Physical Biology CIB-CSIC Ramiro de Maeztu 9 28040 Madrid (Spain);

    Molecular Recognition and Host-Pathogen Interactions CIC bioGUNE Bizkaia Technology Park Building 801 A 48170 Derio (Spain);

    Glycotechnology Laboratory CICbiomaGUNE Paseo Miramjn 20014 Donostia-San Sebastian (Spain);

    Molecular Recognition and Host-Pathogen Interactions CIC bioGUNE Bizkaia Technology Park Building 801 A 48170 Derio (Spain);

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 应用化学;
  • 关键词

    fluorine; molecular modeling; molecular recognition; NMR spectroscopy; noncovalent interactions;

    机译：氟;分子建模;分子识别;NMR光谱;非价相互作用;

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