4-methylphenyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-1-thio-β-D-glucopyranoside | 1415974-47-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 4-methylphenyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-1-thio-β-D-glucopyranoside
• 英文别名: 4-methylphenyl 2-azido-4,6-O-(benzylidene)-2-deoxy-3-O-(2-naphthylmethyl)-1-thio-D-glucopyranoside
• CAS: 1415974-47-8
• 化学式: C₃₁H₂₉N₃O₄S
• 分子量: 539.655
• InChiKey: OOFNJVDJZYAMKD-NHMJYFFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.34
• 重原子数：
  39.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  85.68
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  、 2-溴甲基萘 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 4-methylphenyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-1-thio-α-D-glucopyranoside 、 4-methylphenyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2-naphthylmethyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  具有GlcNAc-GlcA重复模式及其与CD44的结合亲和力的透明质酸寡糖的合成。

  摘要：

  透明质酸（HA）是细胞外基质中普遍存在的糖胺聚糖，也是CD44的配体，CD44是一种跨膜糖蛋白，在细胞迁移中很重要。晶体和NMR研究发现，模式（GlcA–GlcNAc）3的六糖是可与CD44结合的最短HA，但是分子动力学模拟显示模式（GlcNAc–GlcA）2的四糖是与CD44相互作用的关键结构。在具有CD44的结合研究中，获得具有这种重复模式的寡聚体至关重要。在这里，我们开发了一种合成程序，可提供带有GlcNAc-GlcA重复单元的HA寡糖，并通过等温滴定量热（ITC）测量了这些糖与人CD44之间的结合相互作用。在化学合成过程中，我们在没有相邻基团参与的情况下成功生成了β-糖苷键，并克服了氧化步骤中的问题。此外，用于脱苄基和叠氮基还原的无氨溶解金属还原已首次应用于碳水化合物合成中。ITC分析表明，HA四糖（GlcNAc–GlcA）2确实可以相互作用并与人CD44结合。

  DOI：

  10.1039/d0ob01048k

文献信息

• Divergent Synthesis of 48 Heparan Sulfate-Based Disaccharides and Probing the Specific Sugar–Fibroblast Growth Factor-1 Interaction
  作者：Yu-Peng Hu、Yong-Qing Zhong、Zhi-Geng Chen、Chun-Yen Chen、Zhonghao Shi、Medel Manuel L. Zulueta、Chiao-Chu Ku、Pei-Ying Lee、Cheng-Chung Wang、Shang-Cheng Hung

  DOI：10.1021/ja3090065

  日期：2012.12.26

  Several biological processes involve glycans, yet understanding their ligand specificities is impeded by their inherent diversity and difficult acquisition. Generating broad synthetic sugar libraries for bioevaluations is a powerful tool in unraveling glycan structural information. In the case of the widely distributed heparan sulfate (HS), however, the 48 theoretical possibilities for its repeating disaccharide call for synthetic approaches that should minimize the effort in an undoubtedly huge undertaking. Here we employed a divergent strategy to afford all 48 HS-based disaccharides from just two orthogonally protected disaccharide precursors. Different combinations and sequence of transformation steps were applied with many downstream intermediates leading up to multiple target products. With the full disaccharide library in hand, affinity screening with fibroblast growth factor-1 (FGF-1) revealed that four of the synthetic sugars bind to FGF-1. The molecular details of the interaction were further clarified through X-ray analysis of the sugar-protein cocrystals. The capability of comprehensive sugar libraries in providing key insights in glycan-ligand interaction is, thus, highlighted.