benzyl (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-rhamnopyranoside | 502423-58-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl (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-rhamnopyranoside
• 英文别名: Bz(-2)[ClAc(-3)][Bz(-4)]Rha(a1-3)[Bz(-2)][Bz(-4)]Rha(a1-2)[Bz(-3)][Bz(-4)]Rha(a)-O-Bn；[(2S,3S,4R,5R,6R)-4-benzoyloxy-5-[(2S,3R,4R,5S,6S)-3,5-dibenzoyloxy-4-[(2S,3R,4R,5S,6S)-3,5-dibenzoyloxy-4-(2-chloroacetyl)oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-2-methyl-6-phenylmethoxyoxan-3-yl] benzoate
• CAS: 502423-58-7
• 化学式: C₆₉H₆₃ClO₂₀
• 分子量: 1247.7
• InChiKey: AAZAOAWFXWNADT-OGULABTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.3
• 重原子数：
  90
• 可旋转键数：
  28
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  240
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  benzyl (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-rhamnopyranoside 在 硫脲 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以83%的产率得到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
  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：

  benzyl (2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 硫脲 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 16.25h， 生成 benzyl (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-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of the pentasaccharide repeating unit of the major O-antigen component from Pseudomonas syringae pv. ribicola NVPPB 1010

  摘要：

  The synthesis of the repeating unit of the major O-antigen component from Pseudomonas syringae pv. ribicola NVPPB 1010 is reported. The strategy used was based on the successive coupling of a trisaccharide rhamnosyl trichloroacetimidate with a rhamnosyl acceptor with a free hydroxyl group on C-2. The pentasaccharide was then obtained by coupling with a N-Troc-tri-O-acetyl-glucosamine trichloroacetimidate. The synthesis allowed the oligomerisation of the repeating unit. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.10.002

文献信息

• Synthesis of the pentasaccharide repeating unit of the major O-antigen component from Pseudomonas syringae pv. ribicola NVPPB 1010
  作者：Emiliano Bedini、Gaspare Barone、Carlo Unverzagt、Michelangelo Parrilli

  DOI：10.1016/j.carres.2003.10.002

  日期：2004.1

  The synthesis of the repeating unit of the major O-antigen component from Pseudomonas syringae pv. ribicola NVPPB 1010 is reported. The strategy used was based on the successive coupling of a trisaccharide rhamnosyl trichloroacetimidate with a rhamnosyl acceptor with a free hydroxyl group on C-2. The pentasaccharide was then obtained by coupling with a N-Troc-tri-O-acetyl-glucosamine trichloroacetimidate. The synthesis allowed the oligomerisation of the repeating unit. (C) 2003 Elsevier Ltd. All rights reserved.
• Structure-Dependent Modulation of a Pathogen Response in Plants by Synthetic O-Antigen Polysaccharides
  作者：Emiliano Bedini、Cristina De Castro、Gitte Erbs、Lorenzo Mangoni、J. Maxwell Dow、Mari-Anne Newman、Michelangelo Parrilli、Carlo Unverzagt

  DOI：10.1021/ja0452166

  日期：2005.3.1

  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).