[2-(2-decyloxyethoxy)ethylsulfanylmethyl]benzene | 1026270-95-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [2-(2-decyloxyethoxy)ethylsulfanylmethyl]benzene
• 英文别名: 2-(2-Decoxyethoxy)ethylsulfanylmethylbenzene
• CAS: 1026270-95-0
• 化学式: C₂₁H₃₆O₂S
• 分子量: 352.582
• InChiKey: NBGPBEWVOOZXFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  24
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [2-(2-decyloxyethoxy)ethylsulfanylmethyl]benzene 在 三氟化硼乙醚 、 氨 、 sodium 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 1-{2-[2-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranosyl)ethoxy]ethoxy}decane
  参考文献：
  名称：

  Carbohydrate–protein interactions at interfaces: synthesis of thiolactosyl glycolipids and design of a working model for surface plasmon resonance

  摘要：

  用于碳水化合物-蛋白质结合研究的硫代半乳糖脂已经合成。其中一种代表被选用于与植物凝集素RCA120（蓖麻的凝集素）结合的研究。使用BIAcore表面等离子共振仪器实时定量测量了相互作用。用β-半乳糖苷酶从硫代半乳糖脂中原位去除大部分半乳糖表明凝集素结合具有高度特异性。1-{2-[2-(2-[β-D-半乳糖基-(1 → 4)-1-硫代-β-D-吡喃葡萄糖基]乙氧基)乙氧基]乙氧基}十八烷30的解离常数KD=8.77×10-8 M，比溶液中与乳糖结合的解离常数高四个数量级。需要浓度大于80mM的乳糖才能阻止凝集素与新膜中的硫代半乳糖脂结合。

  DOI：

  10.1039/b210672h
• 作为产物：
  描述：

  癸基溴 、 2-(2-benzylsulfanylethoxy)ethanol 在 phase transfer catalyst sodium iodide 作用下， 生成 [2-(2-decyloxyethoxy)ethylsulfanylmethyl]benzene
  参考文献：
  名称：

  Carbohydrate–protein interactions at interfaces: comparison of the binding of Ricinus communis lectin to two series of synthetic glycolipids using surface plasmon resonance studies

  摘要：

  合成了两种C-乳糖脂和相关的C-半乳糖脂，并将它们与RCA120植物凝集素的结合情况与第二系列的硫乳糖乙氧烷进行比较。通过表面等离子共振（BIAcore）在5至30°C范围内的不同浓度和温度下实时定量测量了互动。C-半乳糖脂（1,3-二甲基-5-[β-D-半乳糖吡喃糖基]-5-(4-辛烷基氧苯基)嘧啶-2,4,6-三酮）与RCA120的结合明显较弱，结合常数KA = 8.86 × 10^5，远低于相应的C-乳糖脂（1,3-二甲基-5-[β-D-半乳糖吡喃糖基-(1→4)-β-D-葡萄糖吡喃糖基]-5-(4-辛烷基氧苯基)嘧啶-2,4,6-三酮）（KA = 2.31 × 10^7）。两种不同系列乳糖脂的连接区域对RCA120凝集素结合的影响清晰可见，结合的动力学值以及自由能中焓和熵的变化反映了连接器及持有合成糖脂在新膜中的烃锚的重要性。

  DOI：

  10.1039/b306784j

文献信息

• Carbohydrate–protein interactions at interfaces: comparison of the binding of Ricinus communis lectin to two series of synthetic glycolipids using surface plasmon resonance studies
  作者：P. Critchley、G. J. Clarkson

  DOI：10.1039/b306784j

  日期：——

  Two C-lactosyl lipids and the related C-galactosyl lipids have been synthesised and their binding to RCA120 plant lectin was compared with a second series of thiolactosylethoxyalkanes. The interactions were measured quantitatively in real time by surface plasmon resonance (BIAcore) at a range of concentrations and temperatures from 5 to 30 °C. The C-galactosyl lipid (1,3-dimethyl-5-[β-D-galactopyranosyl]-5-(4-octadecyloxybenzyl)pyrimidine-2,4,6-trione) bound much more weakly with a KA = 8.86 × 105 than the corresponding C-lactosyl lipid (1,3-dimethyl-5-[β-D-galactopyranosyl-(1 → 4)-β-D-glucopyranosyl]-5-(4-octadecyloxybenzyl)pyrimidine-2,4,6-trione) (KA = 2.31 × 107). The influence of the linker region of the two different series of lactosyl lipids was clearly demonstrated by the differences in the binding to RCA120 lectin. The changes in kinetic values and in the enthalpic and entropic contribution to the free energy of binding reflected the importance of the linker and the hydrocarbon anchor holding the synthetic glycolipids in the neomembrane.

  合成了两种C-乳糖脂和相关的C-半乳糖脂，并将它们与RCA120植物凝集素的结合情况与第二系列的硫乳糖乙氧烷进行比较。通过表面等离子共振（BIAcore）在5至30°C范围内的不同浓度和温度下实时定量测量了互动。C-半乳糖脂（1,3-二甲基-5-[β-D-半乳糖吡喃糖基]-5-(4-辛烷基氧苯基)嘧啶-2,4,6-三酮）与RCA120的结合明显较弱，结合常数KA = 8.86 × 10^5，远低于相应的C-乳糖脂（1,3-二甲基-5-[β-D-半乳糖吡喃糖基-(1→4)-β-D-葡萄糖吡喃糖基]-5-(4-辛烷基氧苯基)嘧啶-2,4,6-三酮）（KA = 2.31 × 10^7）。两种不同系列乳糖脂的连接区域对RCA120凝集素结合的影响清晰可见，结合的动力学值以及自由能中焓和熵的变化反映了连接器及持有合成糖脂在新膜中的烃锚的重要性。
• Carbohydrate–protein interactions at interfaces: synthesis of thiolactosyl glycolipids and design of a working model for surface plasmon resonance
  作者：Peter Critchley、M. Nicolas Willand、Atvinder K. Rullay、David H. G. Crout

  DOI：10.1039/b210672h

  日期：2003.3.13

  Thiolactosyl lipids designed for carbohydrate-protein binding studies have been synthesised. One representative was selected for binding studies with a plant lectin RCA120, the agglutinin from Ricinus communis. The interactions were measured quantitatively in real time using a BIAcore surface plasmon resonance instrument. Removal of much of the galactose from the thiolactosyl lipid in situ with β-galactosidase showed that the lectin binding was highly specific. A dissociation constant KD = 8.77 × 10−8 M was measured for 1-2-[2-(2-[β-D-galactopyranosyl-(1 → 4)-1-thio-β-D-glucopyranosyl]ethoxy)ethoxy]ethoxy}octadecane 30 which is four orders of magnitude greater than that determined for binding to lactose in solution. A concentration of lactose of >80 mM was required to block the lectin binding to thiolactosyl lipid in a neomembrane.

  用于碳水化合物-蛋白质结合研究的硫代半乳糖脂已经合成。其中一种代表被选用于与植物凝集素RCA120（蓖麻的凝集素）结合的研究。使用BIAcore表面等离子共振仪器实时定量测量了相互作用。用β-半乳糖苷酶从硫代半乳糖脂中原位去除大部分半乳糖表明凝集素结合具有高度特异性。1-2-[2-(2-[β-D-半乳糖基-(1 → 4)-1-硫代-β-D-吡喃葡萄糖基]乙氧基)乙氧基]乙氧基}十八烷30的解离常数KD=8.77×10-8 M，比溶液中与乳糖结合的解离常数高四个数量级。需要浓度大于80mM的乳糖才能阻止凝集素与新膜中的硫代半乳糖脂结合。