didodecyl N-(3-carboxypropanoyl)-L-glutamate | 140161-56-4

• 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: didodecyl N-(3-carboxypropanoyl)-L-glutamate
• 英文别名: glutamate dodecyl ester-type succinic acid；4-[[(2S)-1,5-didodecoxy-1,5-dioxopentan-2-yl]amino]-4-oxobutanoic acid
• CAS: 140161-56-4
• 化学式: C₃₃H₆₁NO₇
• 分子量: 583.85
• InChiKey: FRAPPCIGEYOWAX-LJAQVGFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  41
• 可旋转键数：
  32
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  didodecyl N-(3-carboxypropanoyl)-L-glutamate 、 N,N'-[iminobis(trimethylene)]-bis[quinamide] 在 三乙胺 、 氯甲酸异丁酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.5h， 以54%的产率得到(S)-2-[3-(Bis-{3-[((3R,5R)-1,3,4,5-tetrahydroxy-cyclohexanecarbonyl)-amino]-propyl}-carbamoyl)-propionylamino]-pentanedioic acid didodecyl ester
  参考文献：
  名称：

  Preparation of gemini-type amphiphiles bearing cyclitol head groups and their application as high-performance modifiers for lipases

  摘要：

  Five gemini-type amphiphiles bearing cyclitol head groups, which have abundance of axial hydroxy groups, are newly synthesized. The syntheses are based on a common mixed anhydride method utilizing N,N'-[iminobis(trimethylene)]bisquinamide, prepared from iminobispropylamine and quino-1,5-lactone, and dialkyl N-(3-carboxypropanoyl)-L-glutamates as polar and hydrophobic components, respectively. Candida rugosa lipase (CRL) and Pseudomonas cepacia lipase (PCL) are co-lyophilized with these synthesized gemini-type amphiphiles, and their transesterification activities in organic solvents are evaluated. The modified PCL and CRL prepared by using each amphiphile showed highly enhanced and moderately enhanced enzyme activity, respectively. These results are discussed in terms of the increased preferential exclusion of the hydrophilic heads of the amphiphile and of the topological view of the amphiphile. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.12.006
• 作为产物：
  描述：

  L-谷氨酸 生成 didodecyl N-(3-carboxypropanoyl)-L-glutamate
  参考文献：
  名称：

  由具有低聚丙烯酸头基团的二烷基 L-谷氨酸两亲物形成的端粒-双层膜的相变诱导亚甲基蓝的非凡单体-二聚体转变

  摘要：

  制备了由具有低聚丙烯酸头基团的 L-谷氨酸二烷基酯形成的新型阴离子调聚物双层。亚甲蓝与这些双层相互作用形成单体和二聚体。由于双层基质的凝胶到液晶相转变，这些单体物质被转化为二聚体物质。即使在吖啶橙的情况下也观察到类似的现象。

  DOI：

  10.1246/cl.1992.219

文献信息

• MEDICINAL PREPARATION
  申请人：TORAY INDUSTRIES, INC.

  公开号：EP1787661A1

  公开（公告）日：2007-05-23

  A pharmaceutical preparation has a ligand structure specifically recognizing a target site and an amphiphilic compound having a hydrophobic or amphiphilic group. The pharmaceutical preparation employs an amphiphilic compound of specific structure obtained by introducing a chained hydrophilic group with an appropriate flexibility, and thus becomes a fine particle suited for drug targeting. The pharmaceutical preparation is expected to give a prolonged pharmacological effect. A particulate preparation exhibiting a remarkable site targeting property can be formed. Further, according to the selection of matrix forming material, the drug releasing property can be controlled.

  一种药物制剂具有特异性识别靶位点的配体结构和具有疏水或两性亲和性基团的两性化合物。该药物制剂采用通过引入具有适当柔韧性的链状亲水基团获得的特定结构的两性化合物，因此成为适用于药物靶向的细颗粒。 预计该药物制剂将产生持久的药理效应。可以形成具有显著靶向性能的颗粒制剂。此外，根据基质形成材料的选择，可以控制药物释放性能。
• Induction of protein-like molecular architecture by self-assembly processes
  作者：Gregg B. Fields

  DOI：10.1016/s0968-0896(98)00216-8

  日期：1999.1

  potentially triple-helical structural motifs have been synthesized. The resultant head group structures have been characterized by circular dichroism and NMR spectroscopies. Evidence for a self-assembly process of peptide-amphiphiles has been obtained from: (a) circular dichroism spectra and melting curves characteristic of triple-helices, (b) one- and two-dimensional NMR spectra indicative of stable

  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
• Extraordinary Monomer-Dimer Transition of Methylene Blue Induced by the Phase Transition of Telomer-Bilayer Membranes Formed from Dialkyl L-Glutamate Amphiphiles with Oligo-Acrylic Acid-Head Group
  作者：Hiroshi Hachisako、Yoshiaki Motozato、Ryoichi Murakami、Kimiho Yamada

  DOI：10.1246/cl.1992.219

  日期：1992.2

  L-glutamates with oligo-acrylic acid-head group were prepared. Methylene Blue interacted with these bilayers to form both monomeric and dimeric species. These monomeric species were converted to the dimeric species due to the gel-to-liquid crystalline phase transition of bilayer matrix. A similar phenomenon was observed even in the case of Acridine Orange.

  制备了由具有低聚丙烯酸头基团的 L-谷氨酸二烷基酯形成的新型阴离子调聚物双层。亚甲蓝与这些双层相互作用形成单体和二聚体。由于双层基质的凝胶到液晶相转变，这些单体物质被转化为二聚体物质。即使在吖啶橙的情况下也观察到类似的现象。
• 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.