(1,2-Di-O-hexadecyl-sn-3-glyceryl)-O-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl-(1->3)-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside | 332075-26-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: (1,2-Di-O-hexadecyl-sn-3-glyceryl)-O-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl-(1->3)-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
• CAS: 332075-26-0
• 化学式: C₁₂₉H₁₅₂O₃₃
• 分子量: 2230.61
• InChiKey: OJBULZMAZCHNAB-MDZHEDEDSA-N

反应信息

• 作为反应物：
  描述：

  (1,2-Di-O-hexadecyl-sn-3-glyceryl)-O-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl-(1->3)-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以80%的产率得到(1,2-Di-O-hexadecyl-sn-3-glyceryl)-O-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranosyl-(1->3)-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  Thermodynamic Properties and Swelling Behavior of Glycolipid Monolayers at Interfaces

  摘要：

  Synthetic glycolipids with lactose headgroups (N = 1, 2, and 3) were synthesized, and their thermodynamic properties were systematically studied by Langmuir isotherms using a film balance. The molar transition entropy and the molar latent heat were calculated by applying the Clausius-Clapeyron equation. It has been demonstrated that the phase behavior of the glycolipid monolayers is comparable to that of ordinary phospholipids, despite the lower degree of cooperativity between the larger headgroups. The glycolipid monolayer was transferred onto a solid surface by Langmuir-Blodgett deposition, and the swelling behavior was investigated by ellipsometry. The surface grafting density was precisely controlled, and the water disjoining pressure inside the lactose layer was quantitatively measured. The measured swelling curves were analyzed in terms of the theoretical descriptions for the grafted polymer "brushes". For the lipids with lactose units of N = 2 and 3, the disjoining pressure-thickness relation could fit very well to these theoretical approaches, even though the statistical limit N much greater than 1 is hardly fulfilled. The results suggest entropic effects of the headgroups on the interaction between the neighboring molecules. On the other hand, the theoretical description of the swelling behavior of the lipids with one lactose unit failed due to the "rodlike" structure of lactose. The unique properties of these glycolipids at interfaces, such as (i) the phase behavior comparable to that of ordinary phospholipids and (ii) the "polymer-like" swelling behavior, play very important roles in biological systems. Mimicking the complex interactions between oligosaccharide headgroups in the plasma membranes, the synthetic glycolipids designed in this study are quite realistic models for the glycocalix.

  DOI：

  10.1021/jp0028103
• 作为产物：
  描述：

  (1,2-Di-O-hexadecyl-sn-3-glyceryl)-O-(2,6-di-O-benzoyl-3,4-di-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl-(1->3)-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以94%的产率得到(1,2-Di-O-hexadecyl-sn-3-glyceryl)-O-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl-(1->3)-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Thermodynamic Properties and Swelling Behavior of Glycolipid Monolayers at Interfaces

  摘要：

  Synthetic glycolipids with lactose headgroups (N = 1, 2, and 3) were synthesized, and their thermodynamic properties were systematically studied by Langmuir isotherms using a film balance. The molar transition entropy and the molar latent heat were calculated by applying the Clausius-Clapeyron equation. It has been demonstrated that the phase behavior of the glycolipid monolayers is comparable to that of ordinary phospholipids, despite the lower degree of cooperativity between the larger headgroups. The glycolipid monolayer was transferred onto a solid surface by Langmuir-Blodgett deposition, and the swelling behavior was investigated by ellipsometry. The surface grafting density was precisely controlled, and the water disjoining pressure inside the lactose layer was quantitatively measured. The measured swelling curves were analyzed in terms of the theoretical descriptions for the grafted polymer "brushes". For the lipids with lactose units of N = 2 and 3, the disjoining pressure-thickness relation could fit very well to these theoretical approaches, even though the statistical limit N much greater than 1 is hardly fulfilled. The results suggest entropic effects of the headgroups on the interaction between the neighboring molecules. On the other hand, the theoretical description of the swelling behavior of the lipids with one lactose unit failed due to the "rodlike" structure of lactose. The unique properties of these glycolipids at interfaces, such as (i) the phase behavior comparable to that of ordinary phospholipids and (ii) the "polymer-like" swelling behavior, play very important roles in biological systems. Mimicking the complex interactions between oligosaccharide headgroups in the plasma membranes, the synthetic glycolipids designed in this study are quite realistic models for the glycocalix.

  DOI：

  10.1021/jp0028103

文献信息

• Synthesis and Molecular Tumbling Properties of Sialyl Lewis X and Derived Neoglycolipids
  作者：Christian Gege、Armin Geyer、Richard R. Schmidt

  DOI：10.1002/1521-3765(20020603)8:11<2454::aid-chem2454>3.0.co;2-u

  日期：2002.6.3

  applied to the synthesis of the corresponding Lewis X (LeX) derivatives. The glycolipids were inserted in model membranes, and the tumbling frequencies of the sLex tetrasaccharide epitopes were then analysed by NMR spectroscopy. A nonaethylene glycol spacer decouples the carbohydrate moiety from the membrane mobility while (oligo-)lactoses act as more rigid distance keepers between the Lewis epitope and

  唾液酸化的路易斯X（sLeX）表位已成为生物学研究的主要目标，因为它通过与选择素结合而在炎症中发挥作用。该表位位于糖鞘脂的末端，并且乳糖单元充当神经酰胺部分的间隔基。本文着重于间隔物结构和间隔物长度对sLeX表位迁移率的影响。为此目的，合成了具有一个，两个或三个乳糖单元作为sLeX四糖表位和膜锚之间间隔物的sLex新糖脂1a-c。该合成策略也被应用于相应的Lewis X（LeX）衍生物的合成。将糖脂插入模型膜中，然后通过NMR光谱分析sLex四糖表位的翻转频率。九甘醇间隔基使碳水化合物部分与膜的迁移性脱钩，而（低聚）乳糖酶则充当路易斯表位与膜表面之间更牢固的距离保持物。通过分析旋转相关时间可以量化不同程度的解耦。