[10,10-²H2]octadecanoic acid | 80863-15-6

• 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: [10,10-²H2]octadecanoic acid
• 英文别名: 10,10-dideuteriooctadecanoic acid；10,10-dideuterio-octadecanoic acid；Stearinsaeure-10d(2)
• CAS: 80863-15-6
• 化学式: C₁₈H₃₆O₂
• 分子量: 286.467
• InChiKey: QIQXTHQIDYTFRH-KNXIQCGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.33
• 重原子数：
  20.0
• 可旋转键数：
  16.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  [10,10-²H2]octadecanoic acid 在 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 [10,10-²H2]-(2S,3R,E)-(2-(stearoylamino)-3-hydroxyoctadec-4-en-1-yl)-(2-(dimethyl(prop-2-yn-1-yl)ammonio)ethyl)phosphate
  参考文献：
  名称：

  Novel Raman-tagged sphingomyelin that closely mimics original raft-forming behavior

  摘要：

  Three Raman probes of sphingomyelin (SM) were synthesized and evaluated for their applicability to imaging experiments. One probe containing a hydroxymethyl-1,3-butadiyne moiety in the polar head group showed strong scattering. The solid-state H-2 NMR spectra of this probe in oriented bilayer membrane revealed excellent compatibility with natural SM in phase behavior since the probe undergoes phase separation to form raft-like liquid ordered (L-o) domains in the raft-mimicking mixed bilayers. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.05.014
• 作为产物：
  描述：

  10-(tert-butyldiphenylsilanyloxy)decanoic acid methyl ester 在 1-苯基-1-丙炔 、 4-二甲氨基吡啶 、 Jones reagent 、 lithium aluminium deuteride 、 四丁基氟化铵 、 三乙胺 、 copper dichloride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 7.17h， 生成 [10,10-²H2]octadecanoic acid
  参考文献：
  名称：

  Novel Raman-tagged sphingomyelin that closely mimics original raft-forming behavior

  摘要：

  Three Raman probes of sphingomyelin (SM) were synthesized and evaluated for their applicability to imaging experiments. One probe containing a hydroxymethyl-1,3-butadiyne moiety in the polar head group showed strong scattering. The solid-state H-2 NMR spectra of this probe in oriented bilayer membrane revealed excellent compatibility with natural SM in phase behavior since the probe undergoes phase separation to form raft-like liquid ordered (L-o) domains in the raft-mimicking mixed bilayers. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.05.014

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.