(2R,3S)-2,3-dimethoxy-1,4-bis(N,N-dimethylamino)butane

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2R,3S)-2,3-dimethoxy-1,4-bis(N,N-dimethylamino)butane
• 英文别名: (2S,3R)-2,3-dimethoxy-N,N,N',N'-tetramethylbutane-1,4-diamine
• 化学式: C₁₀H₂₄N₂O₂
• 分子量: 204.313
• InChiKey: VYQCQNCBTMHEFI-AOOOYVTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  24.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2,3-dimethoxy-1,4-bis(N,N-dimethylamino)butane 、 溴代十六烷 以 丙酮 为溶剂， 反应 48.0h， 以65%的产率得到(2R,3S)-2,3-dimethoxy-1,4-bis(n-hexadecyl-N,N-dimethylammonium)butane dibromide
  参考文献：
  名称：

  Counterion-Controlled Transition of a Cationic Gemini from Submicroscopic to Giant Vesicles

  摘要：

  While much is known about the self-assembly of lipids on nanoscale, our understanding of their biologically relevant mesoscale organization remains incomplete. Here, we show for a cationic gemini lipid a sharp and reversible transition from small vesicles with an average diameter of approximately 40 nm to giant vesicles (GVs) with an average diameter of approximately 11 mu m. This transition is dependent on proper [ NaCl] and specific temperature. Below this transition and in the vicinity of the air/water interface, a series of mesoscale morphological transitions was observed, revealing complex structures resembling biological membranes. On the basis of microscopy experiments, a tentative [ NaCl] versus temperature shape/size phase diagram was constructed. To explain this unprecedented transition, we propose a novel mechanism whereby a specific interaction of Cl-counterion with the cationic gemini surfactant initiates the formation of a commensurate solute counterion lattice with low spontaneous curvature. In keeping with the high bending rigidity of NaCl crystal, this tightly associated ionic lattice enslaves membrane curvature and the mesoscale 3-D organization of this lipid.

  DOI：

  10.1021/ja060382u

文献信息

• Counterion-Controlled Transition of a Cationic Gemini from Submicroscopic to Giant Vesicles
  作者：Samppa J. Ryhänen、V. Matti J. Säily、Mikko J. Parry、Paola Luciani、Giovanna Mancini、Juha-Matti I. Alakoskela、Paavo K. J. Kinnunen

  DOI：10.1021/ja060382u

  日期：2006.7.1

  While much is known about the self-assembly of lipids on nanoscale, our understanding of their biologically relevant mesoscale organization remains incomplete. Here, we show for a cationic gemini lipid a sharp and reversible transition from small vesicles with an average diameter of approximately 40 nm to giant vesicles (GVs) with an average diameter of approximately 11 mu m. This transition is dependent on proper [ NaCl] and specific temperature. Below this transition and in the vicinity of the air/water interface, a series of mesoscale morphological transitions was observed, revealing complex structures resembling biological membranes. On the basis of microscopy experiments, a tentative [ NaCl] versus temperature shape/size phase diagram was constructed. To explain this unprecedented transition, we propose a novel mechanism whereby a specific interaction of Cl-counterion with the cationic gemini surfactant initiates the formation of a commensurate solute counterion lattice with low spontaneous curvature. In keeping with the high bending rigidity of NaCl crystal, this tightly associated ionic lattice enslaves membrane curvature and the mesoscale 3-D organization of this lipid.