5-aminopentyl-L-glycero-α-D-manno-heptopyranosyl-L-glycero-α-D-manno-heptopyranoside | 1237498-96-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-aminopentyl-L-glycero-α-D-manno-heptopyranosyl-L-glycero-α-D-manno-heptopyranoside
• 英文别名: SI-1
• CAS: 1237498-96-2
• 化学式: C₁₉H₃₇NO₁₃
• 分子量: 487.502
• InChiKey: CNYAIPFXHRNAHN-KPYMXKMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.52
• 重原子数：
  33.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  245.01
• 氢给体数：
  10.0
• 氢受体数：
  14.0

反应信息

• 作为产物：
  描述：

  在 10% palladium on carbon 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 5-aminopentyl-L-glycero-α-D-manno-heptopyranosyl-L-glycero-α-D-manno-heptopyranoside
  参考文献：
  名称：

  迈向鼠疫耶尔森菌细胞壁多糖的合成：L-甘油-D-甘露聚糖-庚糖结构单元的对映选择性合成。

  摘要：

  描述了用于鼠疫耶尔森氏菌细胞壁多糖的全合成的L-甘油-D-甘露聚糖-庚基结构单元的短且对映选择性的从头合成。

  DOI：

  10.1039/c000784f

文献信息

• Antigenic Potential of a Highly Conserved Neisseria meningitidis Lipopolysaccharide Inner Core Structure Defined by Chemical Synthesis
  作者：Anika Reinhardt、You Yang、Heike Claus、Claney L. Pereira、Andrew D. Cox、Ulrich Vogel、Chakkumkal Anish、Peter H. Seeberger

  DOI：10.1016/j.chembiol.2014.11.016

  日期：2015.1

  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.