1-十六烷醇-D33 | 284474-73-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 1-十六烷醇-D33
• 中文别名: 1-十六烷醇-d₃₃
• 英文名称: 1-hexadecyl-d33-ol
• 英文别名: hexadecyl-d33 alcohol；d33-hexadecanol；1-Hexadecan-d33-ol；1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,14,14,15,15,16,16,16-tritriacontadeuteriohexadecan-1-ol
• CAS: 284474-73-3
• 化学式: C₁₆H₃₄O
• 分子量: 275.183
• InChiKey: BXWNKGSJHAJOGX-TUWMXWROSA-N

物化性质

• 熔点：
  54-56 °C(lit.)
• 沸点：
  179-181 °C10 mm Hg(lit.)
• 密度：
  0.818 g/mL at 25 °C

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  17
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• WGK Germany：
  3
• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38

反应信息

• 作为反应物：
  描述：

  1-十六烷醇-D33 在 咪唑 、 碘 、 三苯基膦 作用下， 以 乙醚 、 乙腈 为溶剂， 以85%的产率得到1-hexadecyl-d33-iodide
  参考文献：
  名称：

  Lipid Modifications of a Ras Peptide Exhibit Altered Packing and Mobility versus Host Membrane as Detected by ²H Solid-State NMR

  摘要：

  The human N-ras protein binds to cellular membranes by insertion of two covalently bound posttranslational lipid modifications, which is crucial for its function in signal transduction and cell proliferation. Mutations in ras may lead to unregulated cell growth and eventually cancer, making it an important therapeutic target. Here we have investigated the molecular details of the membrane binding mechanism. A heptapeptide derived from the C-terminus of the human N-ras protein was synthesized including two hexadecyl modifications. Solid-state H-2 NMR was used to determine the packing and molecular dynamics of the ras lipid chains as well as the phospholipid matrix. Separately labeling the chains of the peptide and the phospholipids with H-2 enabled us to obtain atomically resolved parameters relevant to their structural dynamics. While the presence of ras only marginally affected the packing of DMPC membranes, dramatically lower order parameters (S-CD) were observed for the ras acyl chains indicating modified packing properties. Essentially identical projected lengths of the 16:0 ras chains and the 14:0 DMPC chains were found, implying that the polypeptide backbone is located at the lipid-water interface. Dynamical properties of both the ras and phospholipid chains were determined from spin-lattice H-2 relaxation (R-1Z) measurements. Plots of R-1Z rates versus the corresponding squared segmental order parameters revealed striking differences. We propose the ras peptide is confined to microdomains containing DMPC chains which are in exchange with the bulk bilayer on the H-2 NMR time scale (similar to 10(-5)s). Compared to the host DMPC matrix, the ras lipid modifications are extremely flexible and undergo relatively large amplitude motions. It is hypothesized that this flexibility is a requirement for the optimal anchoring of lipid-modified proteins to cellular membranes.

  DOI：

  10.1021/ja051856c
• 作为产物：
  描述：

  棕榈酸-d31 在 lithium aluminium deuteride 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到1-十六烷醇-D33
  参考文献：
  名称：

  烷硫醇自组装单分子层的分子间和分子内温度依赖性振动扰动

  摘要：

  已在 25-300 K 条件下探索了吸附在 Au(111) 织构表面上的辛硫醇、十二烷硫醇和十六烷硫醇（分别为 C8、C12 和 C16）单分子层的红外光谱。C-H 拉伸模式通常会移动几个波数到较低的频率，并且随着温度的降低强度增加多达 75%，这提供了这些拉伸模式与低能量振动模式耦合等效应的证据。相反，对于低于 300 K 的所有温度，随着氢化吸附物在完全氘化 C16 的基质中越来越稀释，完全氢化的 C16 的 C-H 带的位置移动了几个波数到更高的频率，表明所有带都受到到分子间耦合。

  DOI：

  10.1021/jp031273u

文献信息

• Molecular motions of alkoxysilanes immobilized on silica surfaces: a deuterium NMR study
  作者：Eric C. Kelusky、Colin A. Fyfe

  DOI：10.1021/ja00268a005

  日期：1986.4

  surface-attached chains have been studied by /sup 2/H NMR. Deuterated alkoxysilanes were immobilized on silica gel and investigated both in the solid state and in the presence of solvents. In the solid state, the spectra exhibit motionally narrowed line shapes with the greatest narrowing and therefore the most motion being observed for the longest chains. The motions in the solid state persist to temperatures

  表面附着链的运动动力学已经通过 /sup 2/H NMR 进行了研究。氘代烷氧基硅烷被固定在硅胶上，并在固态和溶剂存在下进行研究。在固态下，光谱表现出运动变窄的线条形状，其中最长的链的变窄幅度最大，因此观察到的运动幅度最大。固态中的运动持续到低至 150 K 的温度，并且本质上可能是各向同性的。己烷和苯对烷氧基硅烷的迁移率只有有限的影响。甲醇能够溶解一部分烷氧基硅烷，但至少有一半的链不受加入甲醇的影响。
• Pyrimidine phosphonic acid esters
  申请人：Concert Pharmaceuticals, Inc.

  公开号：US10160778B2

  公开（公告）日：2018-12-25

  This invention relates to compounds of Formula (I): and pharmaceutically acceptable salts thereof, wherein Y1a, Y1b, Y2a, Y2b, Y3a, and Y3b are each independently selected from hydrogen and deuterium, Y4a, Y4b, Y5a, Y5b, Y6a, Y6b, Y7a, Y7b, Y8a, Y8b, Y9a, Y9b, Y10a, Y10b, Y11a, Y11b, Y12a, Y12b, Y13a, Y13b, Y14a, Y14b, Y15a, Y15b, Y16a, Y16b, Y17a, Y17b, Y18a, and Y18b are each deuterium, X1a, X1b, X2a, X2b, X3, X4a, X4b, X5, and X6 are each independently selected from hydrogen and deuterium; and R is CD3. This invention also provides compositions comprising a compound of this invention and the use of such compositions in methods of treating diseases and conditions that are beneficially treated by administering a viral DNA polymerase inhibitor.

  本发明涉及式（I）化合物： 及其药学上可接受的盐，其中 Y1a、Y1b、Y2a、Y2b、Y3a 和 Y3b 各自独立地选自氢和氘，Y4a、Y4b、Y5a、Y5b、Y6a、Y6b、Y7a、Y7b、Y8a、Y8b、Y9a、Y9b、Y10a、Y10b、Y11a、Y11b、Y12a、Y12b、Y13a、Y13b、Y14a、Y14b、Y15a、Y15b、Y16a、Y16b、Y17a、Y17b、Y18a 和 Y18b 各自为氘，X1a、X1b、X2a、X2b、X3、X4a、X4b、X5 和 X6 各自独立地选自氢和氘；和 R 是 CD3。本发明还提供了包含本发明化合物的组合物，以及这种组合物在治疗通过施用病毒DNA聚合酶抑制剂而获益的疾病和病症的方法中的用途。
• Membrane Insertion of a Lipidated Ras Peptide Studied by FTIR, Solid-State NMR, and Neutron Diffraction Spectroscopy
  作者：Daniel Huster、Alexander Vogel、Catherine Katzka、Holger A. Scheidt、Hans Binder、Silvia Dante、Thomas Gutberlet、Olaf Zschörnig、Herbert Waldmann、Klaus Arnold

  DOI：10.1021/ja0289245

  日期：2003.4.1

  Membrane binding of a doubly lipid modified heptapeptide from the C-terminus of the human N-ras protein was studied by Fourier transform infrared, solid-state NMR, and neutron diffraction spectroscopy. The 16:0 peptide chains insert well into the 1,2-dimyristoyl-sn-glycero-3-phosphocholine phospholipid matrix. This is indicated by a common main phase transition temperature of 21.5 degreesC for both the lipid and peptide chains as revealed by FTIR measurements. Further, H-2 NMR reveals that peptide and lipid chains have approximately the same chain length in the liquid crystalline state. This is achieved by a much lower order parameter of the 16:0 peptide chains compared to the 14:0 phospholipid chains. Finally, proton/deuterium contrast variation of neutron diffraction experiments indicates that peptide chains are localized in the membrane interior analogous to the phospholipid chains. In agreement with this model of peptide chain insertion, the peptide part is localized at the lipid-water interface of the membrane. This is revealed by H-1 nuclear Overhauser enhancement spectra recorded under magic angle spinning conditions. Quantitative cross-peak analysis allows the examination of the average location of the peptide backbone and side chains with respect to the membrane. While the backbone shows the strongest cross-relaxation rates with the phospholipid glycerol, the hydrophobic side chains of the peptide insert deeper into the membrane interior. This is supported by neutron diffraction experiments that reveal a peptide distribution in the lipid-water interface of the membrane. Concurring with these experimental findings, the amide protons of the peptide show strong water exchange as seen in NMR and FTIR measurements. No indications for a hydrogen-bonded secondary structure of the peptide backbone are found. Therefore, membrane binding of the C-terminus of the N-ras protein is mainly due to lipid chain insertion but also supported by interactions between hydrophobic side chains and the lipid membrane. The peptide assumes a mobile and disordered conformation in the membrane. Since the C-terminus of the soluble part of the ras protein is also disordered, we hypothesize that our model for membrane binding of the ras peptide realistically describes the membrane binding of the lipidated C-terminus of the active ras protein.
• PYRIMIDINE PHOSPHONIC ACID ESTERS BEARING AT LEAST ONE DEUTERIUM ATOM
  申请人：Concert Pharmaceuticals Inc.

  公开号：EP3212656B1

  公开（公告）日：2019-06-05
• PYRIMIDINE PHOSPHONIC ACID ESTERS
  申请人：Concert Pharmaceuticals, Inc.

  公开号：US20170334937A1

  公开（公告）日：2017-11-23

  This invention relates to compounds of Formula (A), and pharmaceutically acceptable salts thereof. This invention also provides compositions comprising a compound of this invention and the use of such compositions in methods of treating diseases and conditions that are beneficially treated by administering a viral DNA polymerase inhibitor.