[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] N-[2-[2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxycarbonylamino]ethyldisulfanyl]ethyl]carbamate | 359442-86-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] N-[2-[2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxycarbonylamino]ethyldisulfanyl]ethyl]carbamate
• CAS: 359442-86-7
• 化学式: C₆₀H₁₀₀N₂O₄S₂
• 分子量: 977.597
• InChiKey: HRHHIEGJBGXHBV-YPCQYWAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.4
• 重原子数：
  68
• 可旋转键数：
  21
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] N-[2-[2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxycarbonylamino]ethyldisulfanyl]ethyl]carbamate 在 1,4-dithio-D,L-threitol 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 3.0h， 生成 cholesteryl (2-mercaptoethyl)carbamate
  参考文献：
  名称：

  脂质筏形成：多元不饱和磷脂的关键作用

  摘要：

  导致脂质筏形成的力量了解甚少。迄今为止，大多数注意力都集中在胆固醇和高熔点脂质之间的有吸引力的相互作用上。排斥力很少受到关注。在这里，我们表明，胆固醇的可交换模拟物与液体无序双层中低熔点磷脂的可交换模拟物之间的排斥性相互作用比同一种固醇和高熔点磷脂的可交换模拟物之间的吸引力要强得多。在液体有序双层中。我们得出的结论是，多不饱和磷脂已被广泛视为脂质筏形成的主要参与者。该知识应引起人们对于控制多不饱和磷脂水平以使细胞膜正常发挥功能的兴趣。

  DOI：

  10.1002/anie.201611367
• 作为产物：
  描述：

  胱胺 、 胆固醇甲酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以50%的产率得到[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] N-[2-[2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxycarbonylamino]ethyldisulfanyl]ethyl]carbamate
  参考文献：
  名称：

  胆固醇在生物膜中的结构作用。

  摘要：

  DOI：

  10.1021/ja016199c

文献信息

• Role of Capping Ligands on the Nanoparticles in the Modulation of Properties of a Hybrid Matrix of Nanoparticles in a 2D Film and in a Supramolecular Organogel
  作者：Asish Pal、Aasheesh Srivastava、Santanu Bhattacharya

  DOI：10.1002/chem.200900304

  日期：2009.9.14

  the gelator assembly was found to depend critically on the capping ligands protecting the Au surface of the gold nanoparticles. Transmission electron microscopy (TEM) showed a long‐range directional assembly of certain AuNPs along the gel fibers. Scanning electron microscopy (SEM) images of the freeze‐dried gels and nanocomposites indicate that the morphological transformation in the composite microstructures

  我们在二维膜和三维聚集体中分别引入了由不同配体封端的各种金纳米颗粒（AuNP），它们分别衍生自N-硬脂酰-L-丙氨酸和N-月桂酰-L-丙氨酸。N-硬脂酰基-L-丙氨酸的组装在空气-水界面处提供稳定的薄膜。在N-硬脂酰-L-丙氨酸的空气-水界面中掺入AuNP后，形成了更紧凑的组件。然后，我们检查了的三维组件具有不同的覆盖配体官能化的各种的AuNP的掺入的影响Ñ -lauroyl-大号-丙氨酸，在烃中形成凝胶的化合物。从各种微观和整体性质的评估中可以明显看出，纳米粒子掺入物理凝胶的深远影响。发现AuNP与胶凝剂组件的相互作用主要取决于保护金纳米颗粒的Au表面的封端配体。透射电子显微镜（TEM）显示某些AuNPs沿凝胶纤维的长距离定向组装。冷冻干燥的凝胶和纳米复合材料的扫描电子显微镜（SEM）图像表明，复合材料微观结构中的形态转变在很大程度上取决于纳米粒子的封端剂。差示扫描量热法（DSC）显示，
• A Chemical Sensor for the Liquid-Ordered Phase
  作者：Honghua Cao、Jianbing Zhang、Bingwen Jing、Steven L. Regen

  DOI：10.1021/ja0513988

  日期：2005.6.1

  The mixing properties of exchangeable phospholipids, derived from 1,2-dipalmitoyl-sn-glycero3-phosphoethanolamine and 1,2-distearoyl-sn-glycero-3-phosphoethanolamine, with an exchangeable form of cholesterol have been used to monitor the transition from the liquid-disordered to the liquid-ordered phase in cholesterol-containing bilayers, made from 1,2-dipaimitoyl-sn-glycero-3-phosphocholine and 1,2-distearoyl-sn-glycero-3-phosphocholine, respectively.
• Selective Association of Cholesterol with Long-Chain Phospholipids in Liquid-Ordered Bilayers:  Support for the Existence of Lipid Rafts
  作者：Michihiro Sugahara、Maki Uragami、Steven L. Regen

  DOI：10.1021/ja038102n

  日期：2003.10.1

  Nearest-neighbor recognition experiments, which have been carried out under fluidizing and condensing conditions, using exchangeable dimers derived from 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine, 1,2-distearoyl-sn-glycero-3-phosphoethanolamine, and cholesterol, have provided strong evidence that sterol-phospholipid recognition is limited to the liquid-ordered phase.
• Selective Sterol-Phospholipid Associations in Fluid Bilayers
  作者：Michihiro Sugahara、Maki Uragami、Steven L. Regen

  DOI：10.1021/ja017269i

  日期：2002.4.1

  The nearest-neighbor preferences of three exchangeable lipid monomers (two phospholipids that differ in length, A and B, and a derivative of cholesterol, C) have been quantified in the fluid bilayer state by use of the nearest-neighbor recognition method (Davidson, S. K. M.; Regen, S. L. Chem. Rev. 1997, 97, 1269). Thus, an analysis of the equilibrium dimer distributions has shown that (i) the sterol favors both phospholipids as nearest neighbors relative to other sterol molecules, (ii) that this recognition is selective (i,e., the sterol favors the longer phospholipid as a nearest neighbor over the shorter one, especially when the sterol concentrations in the bilayer is high (e.g., 40 mol %), and (iii) the phospholipids, themselves, are unable to recognize each other. Taken together, these findings indicate that the probable mechanism by which cholesterol induces homoassociation of A and B in analogous bilayers is one in which the sterol "pulls" two or more of the longer phospholipid monomers (B) out of a "sea" of randomly mixed A and B. These findings also lend support for the notion of cholesterol - phospholipid complexation in fluid bilayers. The biological implications of these findings are briefly discussed.
• The Structural Role of Cholesterol in Biological Membranes
  作者：Michihiro Sugahara、Maki Uragami、Xun Yan、Steven L. Regen

  DOI：10.1021/ja016199c

  日期：2001.8.1