N-(1-oxybutyric acid methyl ester)-tris[(aminopropoxy)methyl]aminomethane | 1254963-24-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-(1-oxybutyric acid methyl ester)-tris[(aminopropoxy)methyl]aminomethane
• CAS: 1254963-24-0
• 化学式: C₁₈H₃₈N₄O₆
• 分子量: 406.523
• InChiKey: QHSLUHKNWITYMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.11
• 重原子数：
  28.0
• 可旋转键数：
  19.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  161.15
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  N-(1-oxybutyric acid methyl ester)-tris[(aminopropoxy)methyl]aminomethane 在 水 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 、 lithium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 5.83h， 生成 (S)-1-chloro-9,9-bis((3-(2-chloroacetamido)propoxy)methyl)-2,11,14-trioxo-17-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)-7-oxa-3,10,15-triazaoctadecan-18-oic acid
  参考文献：
  名称：

  Protein assembly directed by synthetic molecular recognition motifs

  摘要：

  三功能化氰尿酸（TCA）和蜜胺（TM）在水溶液中以1:1的化学计量比选择性地相互识别。我们将生物素连接到TCA和TM上，通过生物素-配体结合，使得TCA和TM在链霉亲和素上呈现出伪四面体展示。人工合成的氰尿酸/蜜胺识别能够驱动选择性的蛋白质-蛋白质组装。

  DOI：

  10.1039/c1ob05998j
• 作为产物：
  描述：

  N-(1-oxybutyric acid)-tris[(cyanoethoxy)methyl]aminomethane 在 sodium tetrahydroborate 、 硫酸 、 三氟乙酸 、 nickel dichloride 作用下， 以 甲醇 为溶剂， 反应 26.0h， 生成 N-(1-oxybutyric acid methyl ester)-tris[(aminopropoxy)methyl]aminomethane
  参考文献：
  名称：

  Protein assembly directed by synthetic molecular recognition motifs

  摘要：

  三功能化氰尿酸（TCA）和蜜胺（TM）在水溶液中以1:1的化学计量比选择性地相互识别。我们将生物素连接到TCA和TM上，通过生物素-配体结合，使得TCA和TM在链霉亲和素上呈现出伪四面体展示。人工合成的氰尿酸/蜜胺识别能够驱动选择性的蛋白质-蛋白质组装。

  DOI：

  10.1039/c1ob05998j

文献信息

• Stabilization of vesicular and supported membranes by glycolipid oxime polymers
  作者：Mingming Ma、Soumitra Chatterjee、Meng Zhang、Dennis Bong

  DOI：10.1039/c0cc05137c

  日期：——

  We report herein new synthetic glycolipid dimers and polymers that provide unprecedented stability to both supported (SLBs) and vesicular lipid bilayers against dehydration and serum exposure. These novel physical properties will enable pharmaceutical delivery and development of SLB bioanalytical devices.

  我们在此报道了一种新的合成糖脂二聚体和聚合物，它们能够显著提高支撑脂双层（SLBs）和囊泡脂双层对抗脱水和血清暴露的稳定性。这些新颖的物理特性将有助于制药递送和SLB生物分析装置的开发。
• Adaptable Synthesis of <i>C</i>-Glycosidic Multivalent Carbohydrates and Succinamide-Linked Derivatization
  作者：Gavin J. Miller、John M. Gardiner

  DOI：10.1021/ol102310x

  日期：2010.11.19

  A modular approach to the synthesis of trivalent C-glycosidic carbohydrates is described. The approach is illustrated employing carboxylate-terminated C-glycosidic D-mannose, D-glucose, and D-galactose derivatives with different length C1-linked spacer units and also core units with different length linker units attached. The central core scaffold is additionally functionalized via a succinamide-based, conjugatable linker unit, exemplified in an extended multivalent derivative [31] and a pyrene-bearing fluorsecent-labeled tris-C-mannosyl conjugate [33].
• Lipid Membrane Adhesion and Fusion Driven by Designed, Minimally Multivalent Hydrogen-Bonding Lipids
  作者：Mingming Ma、Yun Gong、Dennis Bong

  DOI：10.1021/ja9072657

  日期：2009.11.25

  Cyanuric acid (CA) and melamine (M) functionalized lipids can form membranes that exhibit robust hydrogen-bond driven surface recognition in water, facilitated by multivalent surface clustering of recognition groups and variable hydration at the lipid-water interface. Here we describe a minimal lipid recognition cluster: three CA or M recognition groups are forced into proximity by covalent attachment to a single lipid headgroup. This trivalent lipid system guides recognition at the lipid-water interface using cyanurate-melamine hydrogen bonding when incorporated at 0.1-5 mol percent in fluid phospholipid membranes, inducing both vesicle-vesicle binding and membrane fusion. Fusion was accelerated when the antimicrobial peptide magainin was used to anchor trivalent recognition, or when added exogenously to a preassembled lipid vesicle complex, underscoring the importance of coupling recognition with membrane disruption in membrane fusion. Membrane apposition and fusion were studied in vesicle suspensions using light scattering, FRET assays for lipid mixing, surface plasmon resonance, and cryo-electron microscopy. Recognition was found to be highly spatially selective as judged by vesicular adhesion to surface patterned supported lipid bilayers (SLBs). Fusion to SLBs was also readily observed by fluorescence microscopy. Together, these studies indicate effective and functional recognition of trivalent phospholipids, despite low mole percentage concentration, solvent competition for hydrogen bond donor/acceptor sites, and simplicity of structure. This novel designed molecular recognition motif may be useful for directing aqueous-phase assembly and biomolecular interactions.