benzyl <(6'-(((naphthylmethyl)amino)carbonyl)hexyl) 5-acetamido-3,5-dideoxy-4-O-(N-((5-(dimethylamino)naphth-1-yl)sulfonyl)glycyl)-8,9-O-isopropylidene-D-glycero-α-D-galacto-nonulopyranosid>onate | 144226-31-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl <(6'-(((naphthylmethyl)amino)carbonyl)hexyl) 5-acetamido-3,5-dideoxy-4-O-(N-((5-(dimethylamino)naphth-1-yl)sulfonyl)glycyl)-8,9-O-isopropylidene-D-glycero-α-D-galacto-nonulopyranosid>onate
• CAS: 144226-31-3
• 化学式: C₅₃H₆₄N₄O₁₃S
• 分子量: 997.176
• InChiKey: IUQJCTVGBLWKPJ-PQJUYCSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.78
• 重原子数：
  71.0
• 可旋转键数：
  22.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  217.36
• 氢给体数：
  4.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  benzyl <(6'-(((naphthylmethyl)amino)carbonyl)hexyl) 5-acetamido-3,5-dideoxy-4-O-(N-((5-(dimethylamino)naphth-1-yl)sulfonyl)glycyl)-8,9-O-isopropylidene-D-glycero-α-D-galacto-nonulopyranosid>onate 在 溶剂黄146 作用下， 反应 40.0h， 以89%的产率得到benzyl <(6'-(((naphthylmethyl)amino)carbonyl)hexyl) 5-acetamido-3,5-dideoxy-4-O-(N-((5-(dimethylamino)naphth-1-yl)sulfonyl)glycyl)-D-glycero-α-D-galacto-nonulopyranosid>onate
  参考文献：
  名称：

  Design and evaluation of a tightly binding fluorescent ligand for influenza A hemagglutinin

  摘要：

  Attachment of influenza virus to susceptible cells is mediated by the viral protein hemagglutinin, which recognizes cell-membrane-bound glycoconjugates that terminate in alpha-sialosides. We have synthesized a fluorescent alpha-sialoside that has the highest affinity of any reported monovalent ligand for hemagglutinin, and it is not a substrate for the viral neuraminidase. This alpha-sialoside provides a convenient fluorescence competition assay for the binding of other ligands. Since each of the currently used binding assays has significant disadvantages, such a simple assay is of great importance for the study of potential inhibitors of viral attachment.

  DOI：

  10.1021/ja00050a004
• 作为产物：
  描述：

  (2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-{6-[(naphthalen-1-ylmethyl)-carbamoyl]-hexyloxy}-6-((1R,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 4-二甲氨基吡啶 、 Dowex 50W (H⁺ form) 、 potassium tert-butylate 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 47.0h， 生成 benzyl <(6'-(((naphthylmethyl)amino)carbonyl)hexyl) 5-acetamido-3,5-dideoxy-4-O-(N-((5-(dimethylamino)naphth-1-yl)sulfonyl)glycyl)-8,9-O-isopropylidene-D-glycero-α-D-galacto-nonulopyranosid>onate
  参考文献：
  名称：

  Design and evaluation of a tightly binding fluorescent ligand for influenza A hemagglutinin

  摘要：

  Attachment of influenza virus to susceptible cells is mediated by the viral protein hemagglutinin, which recognizes cell-membrane-bound glycoconjugates that terminate in alpha-sialosides. We have synthesized a fluorescent alpha-sialoside that has the highest affinity of any reported monovalent ligand for hemagglutinin, and it is not a substrate for the viral neuraminidase. This alpha-sialoside provides a convenient fluorescence competition assay for the binding of other ligands. Since each of the currently used binding assays has significant disadvantages, such a simple assay is of great importance for the study of potential inhibitors of viral attachment.

  DOI：

  10.1021/ja00050a004