bis(1-amino-1-deoxy-D-glucityl)3,6-dioxaoctane | 493020-89-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: bis(1-amino-1-deoxy-D-glucityl)3,6-dioxaoctane
• 英文别名: 1,8-bis(1-deoxy-D-glucitol-1-ylamino)-3,6-dioxaoctane；(2R,3R,4R,5S)-6-[2-[2-[2-[[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]amino]ethoxy]ethoxy]ethylamino]hexane-1,2,3,4,5-pentol
• CAS: 493020-89-6
• 化学式: C₁₈H₄₀N₂O₁₂
• 分子量: 476.522
• InChiKey: BTRJABZSSRFPRA-OVSMWIARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.2
• 重原子数：
  32
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  245
• 氢给体数：
  12
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  bis(1-amino-1-deoxy-D-glucityl)3,6-dioxaoctane 在 sodium cyanoborohydride 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 27.17h， 生成 bis(N-octadecene-9-yl-1-amino-1-deoxy-D-glucityl)3,6-dioxaoctane
  参考文献：
  名称：

  Sugar-Based Gemini Surfactant with a Vesicle-to-Micelle Transition at Acidic pH and a Reversible Vesicle Flocculation near Neutral pH

  摘要：

  A sugar-based (reduced glucose) gemini surfactant forms vesicles in dilute aqueous solution near neutral pH. At lower pH, there is a vesicle-to-micelle transition within a narrow pH region (pH 6.0-5.6). The vesicles are transformed into large cylindrical micelles that in turn are transformed into small globular micelles at even lower pH. In the vesicular pH region, the vesicles are positively charged at pH < 7 and exhibit a good colloidal stability. However, close to pH 7, the vesicles become unstable and rapidly flocculate and eventually sediment out from the solution. We find that the flocculation correlates with low vesicle zeta-potentials and the behavior is thus well predicted by the classical DLVO theory of colloidal stability. Surprisingly, we find that the vesicles are easily redispersed by increasing the pH to above pH 7.5. We show that this is due to a vesicle surface charge reversal resulting in negatively charged vesicles at pH > 7.1. Adsorption, or binding, of hydroxide ions to the vesicular surface is likely the cause for the charge reversal, and a hydroxide ion binding constant is calculated using a Poisson-Boltzmann model.

  DOI：

  10.1021/ja028195t
• 作为产物：
  描述：

  1,8-二氨基-3,6-二氧杂辛烷 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 48.5h， 生成 bis(1-amino-1-deoxy-D-glucityl)3,6-dioxaoctane
  参考文献：
  名称：

  超分子化学，62.配体和共底物对磷酸酯和DNA与镧系元素水解的影响† ‡

  摘要：

  已描述了通过提供具有增加数量的亲核基团的共底物或通过将相应的多元醇共价连接至更强的金属结合中心（如二氮杂冠醚）来增强镧系离子的催化活性的尝试。尽管对双（4-硝基苯基）磷酸酯（BNPP）和超螺旋质粒DNA水解的动力学影响只是中等程度，但它们对共底物结构和多元醇构型的依赖性明确表明它们参与了反应的缓慢步骤。因此，向LaCl 3溶液中添加葡萄糖酸会导致DNA切割从20％显着增加到71％​​。与二氮杂皇冠共价结合的萘单元对BNPP的影响很小水解，但再次将DNA水解从38％（RF II）提高到60％。使用溴化乙锭的荧光测定法对小牛胸腺DNA进行的初步亲和力测量显示，多胺对配体电荷的依赖性如先前观察到的那样。萘化合物的特征是高亲和力。初步的NMR数据表明，萘基单元插入到DNA中。

  DOI：

  10.1002/jlac.199619961109

文献信息

• Synthesis of nonionic reduced-sugar based bola amphiphiles and gemini surfactants with an α,ω-diamino-(oxa)alkyl spacer
  作者：Anno Wagenaar、Jan B.F.N. Engberts

  DOI：10.1016/j.tet.2007.08.023

  日期：2007.10

  Reduced-sugar based gemini surfactants with an alpha,omega-diamino-(oxa) alkyl spacer exhibit a rich pH-dependent aggregation behavior and are efficient DNA carriers in gene transfection. Herein, we describe an improved synthetic procedure for these amphiphiles. First, a series of novel nonionic bolaform amphiphiles with identical headgroups and alpha,omega-diamino-(oxa) alkyl spacers were synthesized by reductive aminations involving alpha,omega-diaminoalkanes and the appropriate sugars or aldehydes. The bolaform compounds were used as starting materials for the synthesis of the corresponding reduced-sugar based gemini surfactants in a reductive alkylation reaction employing a polymer-bound cyanoborohydride. A series of new gemini surfactants have been synthesized and characterized. (C) 2007 Elsevier Ltd. All rights reserved.