8-hydroxy-3,6-dioxaoctyl 2',3',4',6'-tetra-O-acetyl-1'-thio-β-D-galactopyranoside | 132156-09-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 8-hydroxy-3,6-dioxaoctyl 2',3',4',6'-tetra-O-acetyl-1'-thio-β-D-galactopyranoside
• 英文别名: [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[2-[2-(2-hydroxyethoxy)ethoxy]ethylsulfanyl]oxan-2-yl]methyl acetate
• CAS: 132156-09-3
• 化学式: C₂₀H₃₂O₁₂S
• 分子量: 496.533
• InChiKey: BPZNGPFDVBCPOQ-CXQPBAHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  33
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  178
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  8-hydroxy-3,6-dioxaoctyl 2',3',4',6'-tetra-O-acetyl-1'-thio-β-D-galactopyranoside 以 1,4-二氧六环 为溶剂， 反应 1.25h， 生成 <(2',3',4',6'-tetra-O-acetyl-1'-thio-β-D-galactopyranosyl)oxy>-3,6-dioxaoctyl 11-(5-cholesten-3β-yloxy)-3,6,9-trioxaundecanyl 2,5-dichlorophenyl phosphorothioate
  参考文献：
  名称：

  Water-soluble cholesteryl-containing phosphorothioate monogalactosides: synthesis, properties, and use in lowering blood cholesterol by directing plasma lipoproteins to the liver

  摘要：

  The synthesis of several monogalactoside-terminated phosphorothiolated cholesteryl derivatives is described. Monogalactosyl derivatives are coupled by phosphorothiolation to cholesterol by using ethylene glycol units as hydrophilic spacer moieties. The resulting compounds are easily soluble in water. Upon addition of such solutions to human serum (to 2 mM final concentration) the compounds are readily incorporated into lipoproteins. Isolated low-density lipoprotein (LDL) and high-density lipoprotein (HDL), preloaded with the compounds, are rapidly cleared from the circulation by the liver. The hepatic association is blocked by N-acetylgalactosamine, which indicates that galactose-specific recognition sites are responsible for the increased liver uptake. The plasma clearance and hepatic uptake of LDL loaded with the compounds is substantially higher (about 2-fold) than clearance and uptake of HDL containing the compounds. The selectivity of the effects of monogalactoside-terminated phosphorothiolated cholesteryl derivatives on the in vivo behavior of LDL as compared to that of HDL indicates that these compounds might be used to lower specifically LDL levels in patients with a high LDL-cholesterol level.

  DOI：

  10.1021/jm00107a024
• 作为产物：
  描述：

  2-氯乙氧基-2-乙氧基二乙醇 在 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 丁酮 为溶剂， 反应 17.0h， 生成 8-hydroxy-3,6-dioxaoctyl 2',3',4',6'-tetra-O-acetyl-1'-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Water-soluble cholesteryl-containing phosphorothioate monogalactosides: synthesis, properties, and use in lowering blood cholesterol by directing plasma lipoproteins to the liver

  摘要：

  The synthesis of several monogalactoside-terminated phosphorothiolated cholesteryl derivatives is described. Monogalactosyl derivatives are coupled by phosphorothiolation to cholesterol by using ethylene glycol units as hydrophilic spacer moieties. The resulting compounds are easily soluble in water. Upon addition of such solutions to human serum (to 2 mM final concentration) the compounds are readily incorporated into lipoproteins. Isolated low-density lipoprotein (LDL) and high-density lipoprotein (HDL), preloaded with the compounds, are rapidly cleared from the circulation by the liver. The hepatic association is blocked by N-acetylgalactosamine, which indicates that galactose-specific recognition sites are responsible for the increased liver uptake. The plasma clearance and hepatic uptake of LDL loaded with the compounds is substantially higher (about 2-fold) than clearance and uptake of HDL containing the compounds. The selectivity of the effects of monogalactoside-terminated phosphorothiolated cholesteryl derivatives on the in vivo behavior of LDL as compared to that of HDL indicates that these compounds might be used to lower specifically LDL levels in patients with a high LDL-cholesterol level.

  DOI：

  10.1021/jm00107a024

文献信息

• Capture-Tag-Release: A Strategy for Small Molecule Labeling of Native Enzymes
  作者：Aaron R. Van Dyke、Lily S. Etemad、Michael J. Vessicchio、George A. Naclerio、Victoria Jedson

  DOI：10.1002/cbic.201600267

  日期：2016.9.2

  Capture, tag and release: We report a method for tagging native enzymes with small molecules, by exploiting both the coupling and fragmentation properties of the Staudinger ligation. As a proof‐of‐principle, this strategy was applied to the enzyme β‐galactosidase. Importantly, inhibitor release in the final step restored enzyme activity.

  捕获，标记和释放：我们报告了一种利用小分子Staudinger连接的偶联和片段化特性来标记小分子天然酶的方法。作为原理的证明，该策略被应用于β-半乳糖苷酶。重要的是，抑制剂在最后一步的释放恢复了酶的活性。