| 502423-62-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 502423-62-3
• 化学式: C₁₂₉H₁₁₇ClO₃₈
• 分子量: 2310.78
• InChiKey: XSVZBWDICZQTOB-SPQATNBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.46
• 重原子数：
  168.0
• 可旋转键数：
  39.0
• 环数：
  19.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  452.66
• 氢给体数：
  0.0
• 氢受体数：
  38.0

反应信息

• 作为反应物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 22.0h， 以84%的产率得到benzyl α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->2)-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->2)-L-rhamnopyranoside
  参考文献：
  名称：

  Structure-Dependent Modulation of a Pathogen Response in Plants by Synthetic O-Antigen Polysaccharides

  摘要：

  Many phytopathogenic bacteria display lipopolysaccharides (LIPS) with the O-chain repeating unit [alpha-L-Rha-(1-->3)-alpha-L-Rha-(1-->3)-alpha-L-Rha-(1-->2)](n). This trisaccharide unit was synthesized and oligomerized to obtain hexa- and nonasaccharides. The deprotected rhamnans were effective in suppressing the hypersensitive response (HR) and in inducing PR-1 gene expression in Arabidopsis thaliana. Conformational analysis of the oligorhamnans by NMR spectroscopy and molecular dynamics calculations revealed that a coiled structure develops with increasing chain length of the oligosaccharide. This is associated with increasing efficacy in HR suppression and PR-1 gene expression. We therefore infer that the coiled structure of phytopathogenic bacteria is a plant-recognizable pathogen-associated molecular pattern (PAMP).

  DOI：

  10.1021/ja0452166
• 作为产物：
  描述：

  (2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate 、 benzyl(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranoside 在 4 A molecular sieve 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以71%的产率得到
  参考文献：
  名称：

  Structure-Dependent Modulation of a Pathogen Response in Plants by Synthetic O-Antigen Polysaccharides

  摘要：

  Many phytopathogenic bacteria display lipopolysaccharides (LIPS) with the O-chain repeating unit [alpha-L-Rha-(1-->3)-alpha-L-Rha-(1-->3)-alpha-L-Rha-(1-->2)](n). This trisaccharide unit was synthesized and oligomerized to obtain hexa- and nonasaccharides. The deprotected rhamnans were effective in suppressing the hypersensitive response (HR) and in inducing PR-1 gene expression in Arabidopsis thaliana. Conformational analysis of the oligorhamnans by NMR spectroscopy and molecular dynamics calculations revealed that a coiled structure develops with increasing chain length of the oligosaccharide. This is associated with increasing efficacy in HR suppression and PR-1 gene expression. We therefore infer that the coiled structure of phytopathogenic bacteria is a plant-recognizable pathogen-associated molecular pattern (PAMP).

  DOI：

  10.1021/ja0452166