methyl 10,10-dideuteriooctadecanoate | 33509-82-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 10,10-dideuteriooctadecanoate
• 英文别名: (10.10-D2)-Stearinsaeuremethylester；10,10-Dideutero-methyl-octadecanoat；Methyl-10,10-dideutero-octadecanoat；Methyl octadecanoat-10,10-d2；10,10-dideuterio-octadecanoic acid methyl ester
• CAS: 33509-82-9
• 化学式: C₁₉H₃₈O₂
• 分子量: 300.494
• InChiKey: HPEUJPJOZXNMSJ-KBMKNGFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.42
• 重原子数：
  21.0
• 可旋转键数：
  16.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  methyl 10,10-dideuteriooctadecanoate 在 水 、 sodium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.0h， 以94%的产率得到[10,10-²H2]octadecanoic acid
  参考文献：
  名称：

  NMR-based conformational analysis of sphingomyelin in bicelles

  摘要：

  Sphingomyelin (SM) is a common sphingolipid in mammalian membranes and is known to be substantially involved in cellular events such as the formation of lipid rafts. Despite its biological significance, conformation of SM in a membrane environment remains unclear because the noncrystalline property and anisotropic environment of lipid bilayers hampers the application of X-ray crystallography and NMR measurements. In this study, to elucidate the conformation of SM in membranes, we utilized bicelles as a substitute for a lipid bilayer membrane. First, we demonstrated through P-31 NMR, H-2 NMR, and dynamic light scattering experiments that SM forms both oriented and isotropic bicelles by changing the ratio of SM/dihexanoyl phosphatidylcholine. Then, we determined the conformation of SM in isotropic bicelles on the basis of coupling constants and NOE correlations in H-1 NMR and found that the C2-C6 and amide groups of SM take a relatively rigid conformation in bicelles. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.001
• 作为产物：
  描述：

  10-氧代十八烷酸甲酯 在 4-二甲氨基吡啶 、 硼氘化钠 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 二甲基亚砜 为溶剂， 生成 methyl 10,10-dideuteriooctadecanoate
  参考文献：
  名称：

  NMR-based conformational analysis of sphingomyelin in bicelles

  摘要：

  Sphingomyelin (SM) is a common sphingolipid in mammalian membranes and is known to be substantially involved in cellular events such as the formation of lipid rafts. Despite its biological significance, conformation of SM in a membrane environment remains unclear because the noncrystalline property and anisotropic environment of lipid bilayers hampers the application of X-ray crystallography and NMR measurements. In this study, to elucidate the conformation of SM in membranes, we utilized bicelles as a substitute for a lipid bilayer membrane. First, we demonstrated through P-31 NMR, H-2 NMR, and dynamic light scattering experiments that SM forms both oriented and isotropic bicelles by changing the ratio of SM/dihexanoyl phosphatidylcholine. Then, we determined the conformation of SM in isotropic bicelles on the basis of coupling constants and NOE correlations in H-1 NMR and found that the C2-C6 and amide groups of SM take a relatively rigid conformation in bicelles. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.001

文献信息

• NMR-based conformational analysis of sphingomyelin in bicelles
  作者：Toshiyuki Yamaguchi、Takashi Suzuki、Tomokazu Yasuda、Tohru Oishi、Nobuaki Matsumori、Michio Murata

  DOI：10.1016/j.bmc.2011.11.001

  日期：2012.1

  Sphingomyelin (SM) is a common sphingolipid in mammalian membranes and is known to be substantially involved in cellular events such as the formation of lipid rafts. Despite its biological significance, conformation of SM in a membrane environment remains unclear because the noncrystalline property and anisotropic environment of lipid bilayers hampers the application of X-ray crystallography and NMR measurements. In this study, to elucidate the conformation of SM in membranes, we utilized bicelles as a substitute for a lipid bilayer membrane. First, we demonstrated through P-31 NMR, H-2 NMR, and dynamic light scattering experiments that SM forms both oriented and isotropic bicelles by changing the ratio of SM/dihexanoyl phosphatidylcholine. Then, we determined the conformation of SM in isotropic bicelles on the basis of coupling constants and NOE correlations in H-1 NMR and found that the C2-C6 and amide groups of SM take a relatively rigid conformation in bicelles. (C) 2011 Elsevier Ltd. All rights reserved.