5-carboxypentyl 2-O-(2-O-(2-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside | 1069074-60-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 5-carboxypentyl 2-O-(2-O-(2-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside
• 英文别名: 6-[(2S,3S,4S,5R,6R)-3-[(2R,3S,4S,5R,6R)-3-[(2R,3S,4S,5R,6R)-3-[(2R,3S,4R,5R,6R)-3-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyhexanoic acid
• CAS: 1069074-60-7
• 化学式: C₁₁₄H₁₂₄O₂₃
• 分子量: 1862.22
• InChiKey: XIEFWOYYXZFYHV-HMIAZFFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.9
• 重原子数：
  137
• 可旋转键数：
  53
• 环数：
  16.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  242
• 氢给体数：
  2
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  5-carboxypentyl 2-O-(2-O-(2-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 、 N-生物素基-1,6-己烷二胺 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以68%的产率得到N-[6-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]hexyl]-6-[(2S,3S,4S,5R,6R)-3-[(2R,3S,4S,5R,6R)-3-[(2R,3S,4S,5R,6R)-3-[(2R,3S,4R,5R,6R)-3-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyhexanamide
  参考文献：
  名称：

  Biotin Sulfone as a New Tool for Synthetic Oligosaccharide Immobilization: Application to Multiple Analysis Profiling and Surface Plasmonic Analysis of Anti-Candida albicans Antibody Reactivity against α and β (1→2) Oligomannosides

  摘要：

  As a part of our glycoantigen synthetic program for diagnosis and basic analysis of yeast-related pathogenic mechanisms, a library of 1-->2 oligomannosides suitable for immunoanalysis was prepared. The use of biotin sulfone, an oxidized form of biotin, offers a convenient solution for both oligosaccharide synthesis and immobilization on microspheres and surface plasmon resonance sensors. The application of this new strategy for the analysis of anti-Candida albicans antibody response through multiple-analyte profiling technology (Luminex) and with surface plasmonic analysis using biotin tagged synthetic oligosaccharides on avidin coated surfaces was validated using monoclonal antibodies.

  DOI：

  10.1021/jm800099g
• 作为产物：
  描述：

  5-methoxycarbonylpentyl 2-O-(2-O-(2-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 在 sodium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以82%的产率得到5-carboxypentyl 2-O-(2-O-(2-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Biotin Sulfone as a New Tool for Synthetic Oligosaccharide Immobilization: Application to Multiple Analysis Profiling and Surface Plasmonic Analysis of Anti-Candida albicans Antibody Reactivity against α and β (1→2) Oligomannosides

  摘要：

  As a part of our glycoantigen synthetic program for diagnosis and basic analysis of yeast-related pathogenic mechanisms, a library of 1-->2 oligomannosides suitable for immunoanalysis was prepared. The use of biotin sulfone, an oxidized form of biotin, offers a convenient solution for both oligosaccharide synthesis and immobilization on microspheres and surface plasmon resonance sensors. The application of this new strategy for the analysis of anti-Candida albicans antibody response through multiple-analyte profiling technology (Luminex) and with surface plasmonic analysis using biotin tagged synthetic oligosaccharides on avidin coated surfaces was validated using monoclonal antibodies.

  DOI：

  10.1021/jm800099g

文献信息

• Biotin Sulfone as a New Tool for Synthetic Oligosaccharide Immobilization: Application to Multiple Analysis Profiling and Surface Plasmonic Analysis of Anti-<i>Candida albicans</i> Antibody Reactivity against α and β (1→2) Oligomannosides
  作者：Mayeul Collot、Boualem Sendid、Aurélie Fievez、Camille Savaux、Annie Standaert-Vitse、Marc Tabouret、Anne Sophie Drucbert、Pierre Marie Danzé、Daniel Poulain、Jean-Maurice Mallet

  DOI：10.1021/jm800099g

  日期：2008.10.9

  As a part of our glycoantigen synthetic program for diagnosis and basic analysis of yeast-related pathogenic mechanisms, a library of 1-->2 oligomannosides suitable for immunoanalysis was prepared. The use of biotin sulfone, an oxidized form of biotin, offers a convenient solution for both oligosaccharide synthesis and immobilization on microspheres and surface plasmon resonance sensors. The application of this new strategy for the analysis of anti-Candida albicans antibody response through multiple-analyte profiling technology (Luminex) and with surface plasmonic analysis using biotin tagged synthetic oligosaccharides on avidin coated surfaces was validated using monoclonal antibodies.