N-succinyl-Glu^inv(OC16H33)-OC16H33 | 125401-63-0

• 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: N-succinyl-Glu^inv(OC16H33)-OC16H33
• 英文别名: 1,5-di-O-hexadecyl-N-succinyl-L-glutamate；dihexadecyl N-succinyl-L-glutamate；1,5-dihexadecyl-N-succinyl L-glutamate；DHSG；(S)-4-((1,5-Bis(hexadecyloxy)-1,5-dioxopentan-2-yl)amino)-4-oxobutanoic acid；4-[[(2S)-1,5-dihexadecoxy-1,5-dioxopentan-2-yl]amino]-4-oxobutanoic acid
• CAS: 125401-63-0
• 化学式: C₄₁H₇₇NO₇
• 分子量: 696.065
• InChiKey: WTBOZUQAGVMYTM-QNGWXLTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.6
• 重原子数：
  49
• 可旋转键数：
  40
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  7

安全信息

• 危险性防范说明：
  P501,P270,P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313,P301+P312+P330
• 危险性描述：
  H302,H315,H319
• 储存条件：
  存储于室温环境中

制备方法与用途

1,5-二十六烷基N-(3-羧基-1-氧代丙基)-L-谷氨酸是一种脂质，可以用于合成磷脂囊泡，并能有效提高蛋白质的包封效率[1]。

反应信息

• 作为反应物：
  描述：

  N-succinyl-Glu^inv(OC16H33)-OC16H33 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 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 50.0h， 生成 1',3'-dixedecyl N-<1-(N-glycyl-O-benzyl ester)succinyl>-L-glutamate
  参考文献：
  名称：

  Synthetic lipidation of peptides and amino acids: monolayer structure and properties.

  摘要：

  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.

  DOI：

  10.1021/ja00142a019
• 作为产物：
  描述：

  1-十六烷醇 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 22.0h， 生成 N-succinyl-Glu^inv(OC16H33)-OC16H33
  参考文献：
  名称：

  Reagent for introduction of protein or gene

  摘要：

  本发明提供了一种用于将蛋白质或基因引入细胞的试剂。本发明的试剂例如是一种用于将蛋白质或基因引入细胞的试剂，包括以下式(I)-1所代表的阳离子氨基酸型脂质的组合物： （其中在式(I)-1中：L是单键，—CONH—，或—S—S—；M1是—(CH2)k—或—(CH2CH2O)k—（其中k是0到14之间的整数）；m1和m2分别是介于11和21之间的整数（在这方面，当提供一种用于将基因引入细胞的试剂时，排除了m1和m2都为15的情况）。

  公开号：

  US08338643B2

文献信息

• 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
• The role of spacers on the self-assembly of DNA aptamer-amphiphiles into micelles and nanotapes
  作者：Timothy R. Pearce、Brett Waybrant、Efrosini Kokkoli

  DOI：10.1039/c3cc42311e

  日期：——

  The self-assembly of single-stranded DNA (ssDNA) aptamer-amphiphiles was influenced by the choice of spacer used to link the hydrophobic tail and aptamer headgroup. Aptamer-amphiphiles without spacers or with hydrophilic spacers formed globular micelles while amphiphiles with hydrophobic spacers formed bilayer nanotapes, which are the first such structures formed by DNA-amphiphiles.

  单链DNA（ssDNA）氨肽酶的自组装受到连接疏水尾部和氨肽酶头基的间隔物选择的影响。不含间隔物或含亲水间隔物的表链亲和物形成了球状胶束，而含疏水间隔物的表链亲和物则形成了双层纳米带，这是 DNA 表链亲和物首次形成的此类结构。
• CARBOXYLIC ACID-TYPE LIPID, AND LIPID PARTICLE AND LIPID MEMBRANE EACH COMPRISING CARBOXYLIC ACID-TYPE LIPID
  申请人：Toray Industries, Inc.

  公开号：US20210387943A1

  公开（公告）日：2021-12-16

  A carboxylic acid-type lipid can accelerate adhesion or aggregation of platelets even if the carboxylic acid-type lipid does not carry a protein involved in adhesion or aggregation of platelets or a peptide corresponding to an active site of the protein; a lipid particle and a lipid membrane each include the carboxylic acid-type lipid; and a platelet aggregation accelerating agent, a platelet adhesion accelerating agent, a hemostatic agent and a platelet substitute each include the carboxylic acid-type lipid, the lipid particle or the lipid membrane. A carboxylic acid-type lipid is selected from carboxylic acid-type lipids represented by formulas (I) to (VI), a lipid particle includes the carboxylic acid-type lipid, a lipid membrane includes the carboxylic acid-type lipid, and a platelet aggregation accelerating agent, a platelet adhesion accelerating agent, a hemostatic agent and a platelet substitute each include the carboxylic acid-type lipid, the lipid particle or the lipid membrane.

  一种羧酸型脂质即使不携带与血小板粘附或聚集有关的蛋白质或相应的蛋白质活性位点对血小板的粘附或聚集也能加速，脂质颗粒和脂质膜均包括该羧酸型脂质；血小板聚集加速剂、血小板粘附加速剂、止血剂和血小板替代物均包括该羧酸型脂质、脂质颗粒或脂质膜。所述羧酸型脂质选自公式（I）到（VI）所表示的羧酸型脂质，脂质颗粒包括该羧酸型脂质，脂质膜包括该羧酸型脂质，血小板聚集加速剂、血小板粘附加速剂、止血剂和血小板替代物均包括该羧酸型脂质、脂质颗粒或脂质膜。
• Fragment condensation on solid-phase in the synthesis of an amphiphilic glycopeptide from the homophilic recognition domain of epithelial cadherin 1
  作者：Jörg Habermann、Horst Kunz

  DOI：10.1016/s0040-4039(98)00923-x

  日期：1998.7

  The lipo-glycopeptide 6 containing the homophilic recognition motif of mouse epithelial cadherin 1 was synthesised via a fragment condensation on a solid phase linked peptide using an allylic anchor and a pentafluorophenol-based coupling reagent.

  含有小鼠上皮钙粘蛋白1的同源识别基序的脂糖肽6是通过使用烯丙基锚和基于五氟苯酚的偶联剂在固相连接的肽上的片段缩合而合成的。
• 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.