N_α,N_δ-bis(3-aminopropyl)-L-ornithine | 124076-28-4

• 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: N_α,N_δ-bis(3-aminopropyl)-L-ornithine
• 英文别名: (2S)-2,5-bis(3-aminopropylamino)pentanoic acid
• CAS: 124076-28-4
• 化学式: C₁₁H₂₆N₄O₂
• 分子量: 246.353
• InChiKey: CFSPANUDDUAIKH-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  113
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N_α,N_δ-bis(3-aminopropyl)-L-ornithine 在 盐酸 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 2,3-dioleoyloxy-N-[2-(spermine-carboxamido)ethyl]-N,N-dimethyl-1-propanaminum chloride
  参考文献：
  名称：

  一种高效合成阳离子脂质 DOSPA 的方法

  摘要：

  已经开发了一种高效的合成阳离子脂质的策略，N-[2-({2,5-双[(3-氨基丙基)氨基]-1-氧代戊基}氨基)乙基]-N,N-二甲基-2,3-双[(1-oxo-9-octadecenyl)oxy] 与氯化氢的盐 (DOSPA)。它涉及在标准偶联剂存在下连接阳离子头基和疏水部分。

  DOI：

  10.1055/s-2006-949636
• 作为产物：
  描述：

  N_α,N_δ-bis(2-cyanoethyl)-L-ornithine 在 镍 氢气 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以85%的产率得到N_α,N_δ-bis(3-aminopropyl)-L-ornithine
  参考文献：
  名称：

  一种高效合成阳离子脂质 DOSPA 的方法

  摘要：

  已经开发了一种高效的合成阳离子脂质的策略，N-[2-({2,5-双[(3-氨基丙基)氨基]-1-氧代戊基}氨基)乙基]-N,N-二甲基-2,3-双[(1-oxo-9-octadecenyl)oxy] 与氯化氢的盐 (DOSPA)。它涉及在标准偶联剂存在下连接阳离子头基和疏水部分。

  DOI：

  10.1055/s-2006-949636

文献信息

• Precision Templating with DNA of a Virus-like Particle with Peptide Nanostructures
  作者：Yves Ruff、Tyson Moyer、Christina J. Newcomb、Borries Demeler、Samuel I. Stupp

  DOI：10.1021/ja4008003

  日期：2013.4.24

  formed by self-assembly of coiled-coil peptides conjugated at opposite termini with cationic segments and poly(ethylene glycol) (PEG) chains. We found that a high molecular weight of PEG segments was critical for the formation of monodisperse and uniformly shaped filamentous complexes. It is proposed that electrostatic attachment of the nanostructures with sufficiently long PEG segments generates steric

  我们在这里报告了通过封装线性或圆形双链 DNA 模板来制备丝状病毒样颗粒，该模板具有带正电荷的域的预组装蘑菇形纳米结构。这些纳米结构模拟天然丝状病毒的衣壳蛋白，由卷曲螺旋肽在相对末端与阳离子片段和聚（乙二醇）（PEG）链共轭的自组装形成。我们发现高分子量的 PEG 片段对于形成单分散且形状均匀的丝状复合物至关重要。有人提出，具有足够长 PEG 片段的纳米结构的静电附着会产生空间力，从而增加中和的 DNA 模板的刚度。这种硬化抵消了 DNA 模板凝结成环形或多次弯曲的自然趋势。对颗粒的形状和尺寸实现的控制提供了一种策略来创建包含核酸的定义长度的一维超分子纳米结构。
• A Columnar Phase of Dendritic Lipid−Based Cationic Liposome−DNA Complexes for Gene Delivery:  Hexagonally Ordered Cylindrical Micelles Embedded in a DNA Honeycomb Lattice
  作者：Kai K. Ewert、Heather M. Evans、Alexandra Zidovska、Nathan F. Bouxsein、Ayesha Ahmad、Cyrus R. Safinya

  DOI：10.1021/ja055907h

  日期：2006.3.1

  Gene therapy holds great promise as a future approach to fighting disease and is explored in worldwide clinical trials. Cationic liposome (CL)-DNA complexes are a prevalent nonviral delivery vector, but their efficiency requires improvement and the understanding of their mechanism of action is incomplete. As part of our effort to investigate the structure-transfection efficiency relationships of self-assembled CL-DNA vectors, we have synthesized a new, highly charged (16+) multivalent cationic lipid, MVLBG2, with a dendritic headgroup. Our synthetic scheme allows facile variation of the headgroup charge and the spacer connecting hydrophobic and headgroup moieties as well as gram-scale synthesis. Complexes of DNA with mixtures of MVLBG2 and neutral 1,2-dioleoyl-sn-glycerophosphatidylcholine (DOPC) exhibit the well-known lamellar phase at 90 mol % DOPC. Starting at 20 mol % dendritic lipid, however, two novel nonlamellar phases are observed by synchrotron X-ray diffraction. The structure of one of these phases, present in a narrow range of composition around 25 mol % MVLBG2, has been solved. In this novel dual lattice structure, termed H-l(C), hexagonally arranged tubular lipid micelles are surrounded by DNA rods forming a three-dimensionally continuous substructure with honeycomb symmetry. Complexes in the H-l(C) phase efficiently transfect mouse and human cells in culture. Their transfection efficiency, as well as that of the lamellar complexes containing only 10 mol % dendritic lipid, reaches and surpasses that of commercially available, optimized DOTAP-based complexes. In particular, complexes containing MVLBG2 are significantly more transfectant over the entire composition range in mouse embryonic fibroblasts, a cell line empirically known to be hard to transfect.