1',3'-dihexadecyl L-glutamate p-toluenesulfonate | 95992-27-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1',3'-dihexadecyl L-glutamate p-toluenesulfonate
• 英文别名: Tos-OH*H-Glu(OC16H33)-OC16H33；dicetyl L-glutaminate p-toluenesulfonate；1',3'-dihexadecyl L-glutamate tosylate；L-Glutamic acid, dihexadecyl ester, 4-methylbenzenesulfonate；dihexadecyl (2S)-2-aminopentanedioate;4-methylbenzenesulfonic acid
• CAS: 95992-27-1
• 化学式: C₇H₈O₃S*C₃₇H₇₃NO₄
• 分子量: 768.196
• InChiKey: QGKSIUAPVOSBRW-XLQCLRHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.38
• 重原子数：
  53
• 可旋转键数：
  37
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1',3'-dihexadecyl L-glutamate p-toluenesulfonate 在 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 反应 30.0h， 生成 1',3'-dohexadecyl N--L-glutamate
  参考文献：
  名称：

  通过自组装过程诱导蛋白样分子结构。

  摘要：

  最有趣的自组装过程之一是将肽链折叠成天然蛋白质结构。我们已经开发出一种构建具有生物学意义的序列的蛋白样结构基序的方法。亲脂性部分连接到肽链的Nα-氨基上，产生“肽-两亲物”。在脂质溶剂界面处的两亲化合物的比对用于促进肽比对以及结构的起始和繁殖。已经合成了含有潜在三螺旋结构基序的肽-两亲物。所得的头基结构已通过圆二色性和NMR光谱学表征。肽两亲分子自组装过程的证据来自：（a）三重螺旋的圆二色性光谱和熔融曲线特征；（b）指示低温下稳定的三螺旋结构和高温下熔融的三重螺旋的一维和二维NMR光谱，以及（c）脉冲场梯度NMR实验证明了建议的三螺旋和非三螺旋物种之间的不同自扩散系数。本文所述的肽-两亲物提供了使用肽头基团建立稳定的蛋白质结构基序的简单方法。（c）脉冲场梯度NMR实验，证明拟议的三螺旋和非三螺旋物种之间具有不同的自扩散系数。本文所述的肽-两亲物提供了使用肽头基团构建稳定的蛋白质结构基序的简

  DOI：

  10.1016/s0968-0896(98)00216-8
• 作为产物：
  描述：

  L-谷氨酸 、 1-十六烷醇 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 以78%的产率得到1',3'-dihexadecyl L-glutamate p-toluenesulfonate
  参考文献：
  名称：

  Diesters of glutaminic acid: Synthesis and primary pharmacological investigations

  摘要：

  DOI：

  10.1007/bf00772105

文献信息

• Synthetic lipidation of peptides and amino acids: monolayer structure and properties.
  作者：Peter Berndt、Gregg B. Fields、Matthew Tirrell

  DOI：10.1021/ja00142a019

  日期：1995.9

  Novel dialkyl chain amphiphiles containing peptides derived from extracellular matrix collagen ligand sequences have been synthesized using a highly efficient solid-phase approach. These compounds have been shown to form stable monolayers at the air-water interface. Monolayer features are determined by the peptide head group and are dependent on the peptide sequence. The peptide packing implied by the head group area is denser than the packing of a fully hydrated random coil structure. At high surface pressures, peptide amphiphiles can be compressed to molecular areas corresponding to fully extended peptide chains. The interfacial monolayer behavior of the peptide amphiphiles is compared to that of a series of novel compounds containing various amino acids in their head group region. Monolayers of these compounds permit investigation of model membranes containing the functional elements of proteins such as those involved in cell adhesion and signaling.
• Hachisako, Hiroshi; Yamazaki, Tetsuya; Ihara, Hirotaka, Journal of the Chemical Society. Perkin transactions II, 1994, # 7, p. 1671 - 1680
  作者：Hachisako, Hiroshi、Yamazaki, Tetsuya、Ihara, Hirotaka、Hirayama, Chuichi、Yamada, Kimiho

  DOI：——

  日期：——
• Thermodynamic and structural characterization of amino acid-linked dialkyl lipids
  作者：Stephanie Tristram-Nagle、Ruthven N.A.H. Lewis、Joseph W. Blickenstaff、Michael DiPrima、Bruno F. Marques、Ronald N. McElhaney、John F. Nagle、James W. Schneider

  DOI：10.1016/j.chemphyslip.2004.11.001

  日期：2005.3

  Using differential scanning calorimetry (DSC), X-ray diffraction (XRD) and Fourier transform infrared spectroscopy (FI'IR), we determined some thermodynamic and structural parameters for a series of amino acid-linked dialkyl lipids containing a glutamic acid-succinate headgroup, and di-alkyl chains: C12, C14, C16 and C18 in CHES buffer, pH 10. Upon heating, DSC shows that the C12, C14 and annealed C 16 lipids undergo a single transition which XRD shows is from a lamellar, chain ordered subgel phase to a fluid phase. This single transition splits into two transitions for C18, and FTIR shows that the upper main transition is predominantly the melting of the hydrocarbon chains whereas the lower transition involves changes in the headgroup ordering as well as changes in the lateral packing of the chains. For short incubation times at low temperature, the C 16 lipid appears to behave like the C18 lipid, but appropriate annealing at low temperatures indicates that its true equilibrium behavior is like the shorter chain lipids. XRD shows that the C12 lipid readily converts into a highly ordered subgel phase upon cooling and suggests a model with untilted, interdigitated chains and an area of 77.2 angstrom(2)/4 chains, with a distorted orthorhombic unit subcell, a = 9.0 angstrom, b = 4.3 angstrom and beta = 92.7 degrees. As the chain length n increases, subgel formation is slowed, but untilted, interdigitated chains prevail. (c) 2004 Elsevier Ireland Ltd. All rights reserved.
• Liposome-like fucopeptides as sialyl lewis X mimetics
  作者：Chun-Cheng Lin、Teiji Kimura、Shih-Hsiung Wu、Gabriele Weitz-Schmidt、Chi-Huey Wong

  DOI：10.1016/s0960-894x(96)00509-4

  日期：1996.11

  Several fucodipeptides and their liposome-like derivatives were prepared and tested as inhibitors of sialyl Lewis X binding to E-selectin. It has been found that trans-hydroxyproline (D or L) can be used to mimic the galactose residue of sialyl Lewis X, and the mimetic containing 3,4-dihydroxy-D-proline is the most active with IC50 value (50 mu M) 10-fold greater than sialyl Lewis X. Derivatization of a hydroxythreonine-containing fucodipeptides into a covalent liposome-like derivative, however, provides a mimetic with only IC50 similar to 30 mu M. Copyright (C) 1996 Elsevier Science Ltd
• Synthesis and biological activity of N-terminal lipidated and/or fluorescently labeled conjugates of astressin as corticotropin releasing factor antagonists
  作者：Dirk T.S. Rijkers、Jack A.J. den Hartog、Rob M.J. Liskamp

  DOI：10.1016/j.bmc.2004.07.035

  日期：2004.10

  This report describes the synthesis of eight N-terminally modified astressin analogs and their biochemical evaluation as corticotropin releasing factor (CRF) antagonists. The lipidated astressin derivatives were tested on rat CRF receptor type 1 and 2alpha and were found to be active as CRF antagonists (rCRFR1: pA(2) = 7.5-8.3; rCRFR2alpha: pA(2) = 7.5-9.0) with nearly equal activities as compared to unmodified astressin (rCRFR1: pA(2) = 8.3 +/- 0.09; rCRFR2alpha: pA(2) = 8.7 +/- 0.08). (C) 2004 Elsevier Ltd. All rights reserved.