(2R,3R,4S,5R,6R)-2-[(2R,3R,4S,5R)-6-氨基-4,5-二羟基-2-(羟基甲基)四氢吡喃-3-基]氧基-6-(羟基甲基)四氢吡喃-3,4,5-三醇 | 21973-66-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (2R,3R,4S,5R,6R)-2-[(2R,3R,4S,5R)-6-氨基-4,5-二羟基-2-(羟基甲基)四氢吡喃-3-基]氧基-6-(羟基甲基)四氢吡喃-3,4,5-三醇
• 英文名称: Maltosylamine
• 英文别名: (2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R)-6-amino-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 21973-66-0
• 化学式: C₁₂H₂₃NO₁₀
• 分子量: 341.315
• InChiKey: RVOXBKZHFYRXCD-PICCSMPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  195
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4-[6-氨基-8-羟基-2-(2-甲氧基乙氧基)嘌呤-9-基甲基]苯甲酸 、 (2R,3R,4S,5R,6R)-2-[(2R,3R,4S,5R)-6-氨基-4,5-二羟基-2-(羟基甲基)四氢吡喃-3-基]氧基-6-(羟基甲基)四氢吡喃-3,4,5-三醇 在 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 C₂₈H₃₈N₆O₁₄ 、 C₂₈H₃₈N₆O₁₄
  参考文献：
  名称：

  Synthesis and immunostimulatory activity of sugar-conjugated TLR7 ligands

  摘要：

  Toll-like receptors (TLRs) are a type of pattern recognition receptors (PRRs), which are activated by recognizing pathogen-associated molecular patterns (PAMPs). The activation of TLRs initiates innate immune responses and subsequently leads to adaptive immune responses. TLR agonists are effective immuomodulators in vaccine adjuvants for infectious diseases and cancer immunotherapy. In exploring hydrophilic small molecules of TLR7 ligands using the cell-targeted property of a vaccine adjuvant, we conjugated 1V209, a small TLR7 ligand molecule, with various low or middle molecular weight sugar molecules that work as carriers. The sugar-conjugated 1V209 derivatives showed increased water solubility and higher immunostimulatory activity in both mouse and human cells compared to unmodified 1V209. The improved immunostimulatory potency of sugar-conjugates was attenuated by an inhibitor of endocytic process, cytochalasin D, suggesting that conjugation of sugar moieties may enhance the uptake of TLR7 ligand into the endosomal compartment. Collectively our results support that sugar-conjugated TLR7 ligands are applicable to novel drugs for cancer and vaccine therapy.

  DOI：

  10.1016/j.bmcl.2019.126840
• 作为产物：
  描述：

  麦芽糖 在 氨 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 (2R,3R,4S,5R,6R)-2-[(2R,3R,4S,5R)-6-氨基-4,5-二羟基-2-(羟基甲基)四氢吡喃-3-基]氧基-6-(羟基甲基)四氢吡喃-3,4,5-三醇
  参考文献：
  名称：

  Synthesis and immunostimulatory activity of sugar-conjugated TLR7 ligands

  摘要：

  Toll-like receptors (TLRs) are a type of pattern recognition receptors (PRRs), which are activated by recognizing pathogen-associated molecular patterns (PAMPs). The activation of TLRs initiates innate immune responses and subsequently leads to adaptive immune responses. TLR agonists are effective immuomodulators in vaccine adjuvants for infectious diseases and cancer immunotherapy. In exploring hydrophilic small molecules of TLR7 ligands using the cell-targeted property of a vaccine adjuvant, we conjugated 1V209, a small TLR7 ligand molecule, with various low or middle molecular weight sugar molecules that work as carriers. The sugar-conjugated 1V209 derivatives showed increased water solubility and higher immunostimulatory activity in both mouse and human cells compared to unmodified 1V209. The improved immunostimulatory potency of sugar-conjugates was attenuated by an inhibitor of endocytic process, cytochalasin D, suggesting that conjugation of sugar moieties may enhance the uptake of TLR7 ligand into the endosomal compartment. Collectively our results support that sugar-conjugated TLR7 ligands are applicable to novel drugs for cancer and vaccine therapy.

  DOI：

  10.1016/j.bmcl.2019.126840

文献信息

• Synthesis and immunostimulatory activity of sugar-conjugated TLR7 ligands
  作者：Akihito Baba、Masahiro Wakao、Hiroyuki Shinchi、Michael Chan、Tomoko Hayashi、Shiyin Yao、Howard B. Cottam、Dennis A. Carson、Yasuo Suda

  DOI：10.1016/j.bmcl.2019.126840

  日期：2020.2

  Toll-like receptors (TLRs) are a type of pattern recognition receptors (PRRs), which are activated by recognizing pathogen-associated molecular patterns (PAMPs). The activation of TLRs initiates innate immune responses and subsequently leads to adaptive immune responses. TLR agonists are effective immuomodulators in vaccine adjuvants for infectious diseases and cancer immunotherapy. In exploring hydrophilic small molecules of TLR7 ligands using the cell-targeted property of a vaccine adjuvant, we conjugated 1V209, a small TLR7 ligand molecule, with various low or middle molecular weight sugar molecules that work as carriers. The sugar-conjugated 1V209 derivatives showed increased water solubility and higher immunostimulatory activity in both mouse and human cells compared to unmodified 1V209. The improved immunostimulatory potency of sugar-conjugates was attenuated by an inhibitor of endocytic process, cytochalasin D, suggesting that conjugation of sugar moieties may enhance the uptake of TLR7 ligand into the endosomal compartment. Collectively our results support that sugar-conjugated TLR7 ligands are applicable to novel drugs for cancer and vaccine therapy.