N-(1-oxybutyric acid methyl ester)-tris[(cyanoethoxy)methyl]aminomethane | 390358-65-3

• 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[(cyanoethoxy)methyl]aminomethane
• 英文别名: Methyl 4-[[1,3-bis(2-cyanoethoxy)-2-(2-cyanoethoxymethyl)propan-2-yl]amino]-4-oxobutanoate；methyl 4-[[1,3-bis(2-cyanoethoxy)-2-(2-cyanoethoxymethyl)propan-2-yl]amino]-4-oxobutanoate
• CAS: 390358-65-3
• 化学式: C₁₈H₂₆N₄O₆
• 分子量: 394.428
• InChiKey: KJDVRTOFCQNLSC-UHFFFAOYSA-N

物化性质

• 沸点：
  679.8±55.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  28
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  155
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-(1-oxybutyric acid methyl ester)-tris[(cyanoethoxy)methyl]aminomethane 在 sodium tetrahydroborate 、 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 、 nickel dichloride 、 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 29.83h， 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：

  tris(cyanoethoxymethyl)aminomethane 在 硫酸 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 6.0h， 生成 N-(1-oxybutyric acid methyl ester)-tris[(cyanoethoxy)methyl]aminomethane
  参考文献：
  名称：

  用于固相肽合成的基于tris的树枝状大分子接枝核壳型树脂的制备

  摘要：

  由三（羟甲基）氨基甲烷（Tris）合成了一种新型的对称树枝状聚合物单体，并将其反复偶联到核-壳型树脂上。通过树枝化过程，氨基的负载量增加至4.0 mmol g -1树脂。所生产的高负载树状聚合物接枝树脂已成功应用于固相肽合成（SPPS）。

  DOI：

  10.1016/s0040-4039(01)01560-x

文献信息

• 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.