Acetic acid (2R,3R,4S,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-{5-[5-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pentyldisulfanyl]-pentyloxy}-tetrahydro-pyran-4-yl ester | 853782-66-8

• 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: Acetic acid (2R,3R,4S,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-{5-[5-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pentyldisulfanyl]-pentyloxy}-tetrahydro-pyran-4-yl ester
• CAS: 853782-66-8
• 化学式: C₃₈H₅₈O₂₀S₂
• 分子量: 898.999
• InChiKey: UTSJCNMSGKOUCQ-FSQGJVJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  60.0
• 可旋转键数：
  25.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  247.32
• 氢给体数：
  0.0
• 氢受体数：
  22.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-{5-[5-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pentyldisulfanyl]-pentyloxy}-tetrahydro-pyran-4-yl ester 在 甲醇 、 sodium methylate 作用下， 反应 0.5h， 以97%的产率得到5-thioacetoxypentyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl dimer
  参考文献：
  名称：

  Selective Binding of Mannose-Encapsulated Gold Nanoparticles to Type 1 Pili in Escherichia coli

  摘要：

  The synthesis, characterization and biological application of mannose encapsulated gold nanoparticles (m-AuNP) are reported. m-AuNP is well dispersed and very stable without aggregation in the media of broad ion strength and pH ranges. The selective binding of m-AuNP to the mannose adhesin FimH of bacterial type 1 pili is demonstrated using transmission electron microscopy. The competition assay with free mannose suggests that m-AuNP binds FimH better than free mannose does. This work demonstrates that carbohydrate attached nanoparticles can be used as an efficient affinity label and a multi-ligand carrier in a biological system.

  DOI：

  10.1021/ja0200903
• 作为产物：
  描述：

  pent-4-enyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 偶氮二异丁腈 、 硫代乙酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 以80%的产率得到Acetic acid (2R,3R,4S,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-{5-[5-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pentyldisulfanyl]-pentyloxy}-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Selective Binding of Mannose-Encapsulated Gold Nanoparticles to Type 1 Pili in Escherichia coli

  摘要：

  The synthesis, characterization and biological application of mannose encapsulated gold nanoparticles (m-AuNP) are reported. m-AuNP is well dispersed and very stable without aggregation in the media of broad ion strength and pH ranges. The selective binding of m-AuNP to the mannose adhesin FimH of bacterial type 1 pili is demonstrated using transmission electron microscopy. The competition assay with free mannose suggests that m-AuNP binds FimH better than free mannose does. This work demonstrates that carbohydrate attached nanoparticles can be used as an efficient affinity label and a multi-ligand carrier in a biological system.

  DOI：

  10.1021/ja0200903