3,4,6-tri-O-acetyl-2-N-acetamido-2-deoxy-α-D-galactopyranosyloxyethyl methacrylamide | 1443446-11-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-acetyl-2-N-acetamido-2-deoxy-α-D-galactopyranosyloxyethyl methacrylamide
• CAS: 1443446-11-4
• 化学式: C₂₀H₃₀N₂O₁₀
• 分子量: 458.466
• InChiKey: GWBGHPFRTGFLDP-NUABRCLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.65
• 重原子数：
  32.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  155.56
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-N-acetamido-2-deoxy-α-D-galactopyranosyloxyethyl methacrylamide 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以65%的产率得到2-N-acetamido-2-deoxy-α-D-galactopyranosyloxyethyl methacrylamide
  参考文献：
  名称：

  ‘Multicopy Multivalent’ Glycopolymer-Stabilized Gold Nanoparticles as Potential Synthetic Cancer Vaccines

  摘要：

  Mucin-related carbohydrates are overexpressed on the surface of cancer cells, providing a disease-specific target for cancer immunotherapy. Here, we describe the design and construction of peptide-free multivalent glycosylated nanoscale constructs as potential synthetic cancer vaccines that generate significant titers of antibodies selective for aberrant mucin glycans. A polymerizable version of the Tn-antigen glycan was prepared and converted into well-defined glycopolymers by Reversible Addition Fragmentation chain Transfer (RAFT) polymerization. The polymers were then conjugated to gold nanoparticles, yielding 'multicopy-multivalent nanoscale glycoconjugates. Immunological studies indicated that these nanomaterials generated strong and long-lasting production of antibodies that are selective to the Tn-antigen glycan and cross-reactive toward mucin proteins displaying Tn. The results demonstrate proof-of-concept of a simple and modular approach toward synthetic anticancer vaccines based on multivalent glycosylated nanomaterials without the need for a typical vaccine protein component.

  DOI：

  10.1021/ja4046857
• 作为产物：
  描述：

  N-(2-羟乙基)-2-甲基-2-丙烯酰胺 在 三氟甲磺酸三甲基硅酯 、 苯硫酚 、 1,2-双(二苯基膦)乙烷 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 3,4,6-tri-O-acetyl-2-N-acetamido-2-deoxy-α-D-galactopyranosyloxyethyl methacrylamide
  参考文献：
  名称：

  ‘Multicopy Multivalent’ Glycopolymer-Stabilized Gold Nanoparticles as Potential Synthetic Cancer Vaccines

  摘要：

  Mucin-related carbohydrates are overexpressed on the surface of cancer cells, providing a disease-specific target for cancer immunotherapy. Here, we describe the design and construction of peptide-free multivalent glycosylated nanoscale constructs as potential synthetic cancer vaccines that generate significant titers of antibodies selective for aberrant mucin glycans. A polymerizable version of the Tn-antigen glycan was prepared and converted into well-defined glycopolymers by Reversible Addition Fragmentation chain Transfer (RAFT) polymerization. The polymers were then conjugated to gold nanoparticles, yielding 'multicopy-multivalent nanoscale glycoconjugates. Immunological studies indicated that these nanomaterials generated strong and long-lasting production of antibodies that are selective to the Tn-antigen glycan and cross-reactive toward mucin proteins displaying Tn. The results demonstrate proof-of-concept of a simple and modular approach toward synthetic anticancer vaccines based on multivalent glycosylated nanomaterials without the need for a typical vaccine protein component.

  DOI：

  10.1021/ja4046857