N-phenyl trifluoroacetimidate (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1→ 2)-3,7-di-O-benzoyl-4-O-para-bromobenzyl-6-O-benzyl-L-glycero-D-mannoheptopyranoside | 1403362-21-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-phenyl trifluoroacetimidate (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1→ 2)-3,7-di-O-benzoyl-4-O-para-bromobenzyl-6-O-benzyl-L-glycero-D-mannoheptopyranoside
• CAS: 1403362-21-9
• 化学式: C₅₅H₅₂BrF₃N₄O₁₆
• 分子量: 1161.93
• InChiKey: BAPMEXSUBUGKRR-QURINYHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.25
• 重原子数：
  79.0
• 可旋转键数：
  21.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  248.0
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  N-phenyl trifluoroacetimidate (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1→ 2)-3,7-di-O-benzoyl-4-O-para-bromobenzyl-6-O-benzyl-L-glycero-D-mannoheptopyranoside 、 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Antigenic Potential of a Highly Conserved Neisseria meningitidis Lipopolysaccharide Inner Core Structure Defined by Chemical Synthesis

  摘要：

  Neisseria meningitidis is a leading cause of bacterial meningitis worldwide. We studied the potential of synthetic lipopolysaccharide (LPS) inner core structures as broadly protective antigens against N. meningitidis. Based on the specific reactivity of human serum antibodies to synthetic LPS cores, we selected a highly conserved LPS core tetrasaccharide as a promising antigen. This LPS inner core tetrasaccharide induced a robust IgG response in mice when formulated as an immunogenic glycoconjugate. Binding of raised mouse serum to a broad collection of N. meningitidis strains demonstrated the accessibility of the LPS core on viable bacteria. The distal trisaccharide was identified as the crucial epitope, whereas the proximal Kdo moiety was immunodominant and induced mainly nonprotective antibodies that are responsible for lack of functional protection in polyclonal serum. Our results identified key antigenic determinants of LPS core glycan and, hence, may aid the design of a broadly protective immunization against N. meningitidis.

  DOI：

  10.1016/j.chembiol.2014.11.016
• 作为产物：
  描述：

  5-tert-butyl-2-methylphenyl 3,7-di-O-benzoyl-4-O-para-bromobenzyl-6-O-benzyl-1-thio-L-glycero-D-manno-heptopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 三氟甲磺酸三甲基硅酯 、 水 、 potassium carbonate 作用下， 以 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 1.5h， 生成 N-phenyl trifluoroacetimidate (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1→ 2)-3,7-di-O-benzoyl-4-O-para-bromobenzyl-6-O-benzyl-L-glycero-D-mannoheptopyranoside
  参考文献：
  名称：

  Total synthesis of the core tetrasaccharide of the lipopolysaccharide from Neisseria meningitidis

  摘要：

  本发明涉及从脑膜炎奈瑟氏菌的脂多糖中全合成α-GlcNAc-(1→2)-α-Hep-(1→3)-α-Hep-(1→5)-α-Kdo核心四糖，所得的产物以及α-GlcNAc-(1→2)-α-Hep-(1→3)-α-Hep-(1→5)-α-Kdo用作疫苗，用于预防由含有四糖的细菌感染引起的疾病，特别是用于预防由脑膜炎奈瑟氏菌引起的脑膜炎、败血症、肺炎和鼻咽炎的免疫。

  公开号：

  EP2573100A1