2-aminoethyl fucoside | 864968-00-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-aminoethyl fucoside
• CAS: 864968-00-3
• 化学式: C₉H₁₉NO₅
• 分子量: 221.254
• InChiKey: MNTSFXCVZOQJBB-JTPBWFLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.82
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  105.17
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-aminoethyl fucoside 、 fluorescein 5-isothiocyanate 在 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 以96%的产率得到
  参考文献：
  名称：

  Discovery of Two Classes of Potent Glycomimetic Inhibitors of Pseudomonas aeruginosa LecB with Distinct Binding Modes

  摘要：

  The treatment of infections due to the opportunistic pathogen Pseudomonas aeruginosa is often difficult, as a consequence of bacterial biofilm formation. Such a protective environment shields the bacterium from host defense and antibiotic treatment and secures its survival. One crucial factor for maintenance of the biofilm architecture is the carbohydrate-binding lectin LecB. Here, we report the identification of potent mannose-based LecB inhibitors from a screening of four series of mannosides in a novel competitive binding assay for LecB. Cinnamide and sulfonamide derivatives are inhibitors of bacterial adhesion with up to a 20-fold increase in affinity to LecB compared to the natural ligand methyl mannoside. Because many lectins of the host require terminal saccharides (e.g., fucosides), such capped structures as reported here may offer a beneficial selectivity profile for the pathogenic lectin. Both classes of compounds show distinct binding modes at the protein, offering the advantage of a simultaneous development of two new lead structures as anti-pseudomonadal drugs with an anti-virulence mode of action.

  DOI：

  10.1021/cb400371r
• 作为产物：
  描述：

  乙基2,3,4-三-O-苄基-1-硫代-alpha,beta-L-吡喃岩藻糖苷 在 palladium dihydroxide 四乙基溴化铵 、 氢气 、 溴 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 106.5h， 生成 2-aminoethyl fucoside
  参考文献：
  名称：

  以多价形式呈现不同碳水化合物配体的 E-选择素拮抗剂的合成和生物学评价

  摘要：

  报道了以多价形式呈现不同碳水化合物配体的第一种多聚赖氨酸缀合物的合成。如 1 H NMR 所示，已制备具有高度可预测的组成的糖聚合物 3c 和 3d。它们起到多价 E-选择素抑制剂的作用，但与先前描述的相关化合物相比，它们的效力并不优越。

  DOI：

  10.1055/s-2005-865299

文献信息

• Combating DC‐SIGN‐mediated SARS‐CoV‐2 dissemination by glycan‐mimicking polymers
  作者：Jonathan Cramer、Xiaohua Jiang、Butrint Aliu、Beat Ernst

  DOI：10.1002/ardp.202300396

  日期：2024.4

  Many viruses exploit the human C‐type lectin receptor dendritic cell‐specific ICAM‐3 grabbing nonintegrin (DC‐SIGN) for cell entry and virus dissemination. An inhibition of DC‐SIGN‐mediated virus attachment by glycan‐derived ligands has, thus, emerged as a promising strategy toward broad‐spectrum antiviral therapeutics. In this contribution, several cognate fragments of oligomannose‐ and complex‐type glycans grafted onto a poly‐l‐lysine scaffold are evaluated as polyvalent DC‐SIGN ligands. The range of selected carbohydrate epitopes encompasses linear (α‐ d‐Man‐(1→2)‐α‐ d‐Man, α‐ d‐Man‐(1→2)‐α‐ d‐Man‐(1→2)‐α‐ d‐Man‐(1→3)‐α‐ d‐Man) and branched (α‐ d‐Man‐(1→6)‐[α‐ d‐Man‐(1→3)]‐α‐ d‐Man) oligomannosides, as well as α‐ l‐Fuc. The thermodynamics of binding are investigated on a mono‐ and multivalent level to shed light on the molecular details of the interactions with the tetravalent receptor. Cellular models of virus attachment and DC‐SIGN‐mediated virus dissemination reveal a high potency of the presented glycopolymers in the low pico‐ and nanomolar ranges, respectively. The high activity of oligomannose epitopes in combination with the biocompatible properties of the poly‐ l‐lysine scaffold highlights the potential for further preclinical development of polyvalent DC‐SIGN ligands.

  摘要 许多病毒利用人类 C 型凝集素受体树突状细胞特异性 ICAM-3 抓取非整合素（DC-SIGN）进入细胞并传播病毒。因此，通过糖源配体抑制 DC-SIGN 介导的病毒附着已成为广谱抗病毒疗法的一种有前途的策略。在本文中，我们评估了接枝到聚赖氨酸支架上的低聚甘露糖和复合型聚糖的几种同源片段作为多价 DC-SIGN 配体。所选碳水化合物表位的范围包括线性（α- d-Man-(1→2)-α- d-Man，α- d-Man-(1→2)-α- d-Man-(1→2)-α- d-Man-(1→3)-α- d-Man）和支化（α- d-Man-(1→6)-[α- d-Man-(1→3)]-α- d-Man）低聚甘露糖苷以及α- l-Fuc。研究了单价和多价结合的热力学，以揭示与四价受体相互作用的分子细节。病毒附着和 DC-SIGN 介导的病毒传播的细胞模型显示，所展示的糖聚合物分别在低皮摩尔和纳摩尔范围内具有很高的效力。低聚甘露糖表位的高活性与聚 l-lysine 支架的生物相容性，凸显了进一步临床前开发多价 DC-SIGN 配体的潜力。