stilbene-4,4'-dicarboxylic acid N,N'-bis(3-hydroxypropyl)diamide | 166824-90-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: stilbene-4,4'-dicarboxylic acid N,N'-bis(3-hydroxypropyl)diamide
• 英文别名: 4,4'-(Ethene-1,2-diyl)bis(N-(3-hydroxypropyl)benzamide)；N-(3-hydroxypropyl)-4-[(E)-2-[4-(3-hydroxypropylcarbamoyl)phenyl]ethenyl]benzamide
• CAS: 166824-90-4
• 化学式: C₂₂H₂₆N₂O₄
• 分子量: 382.459
• InChiKey: LKUUKRTUUJSTLE-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  98.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  stilbene-4,4'-dicarboxylic acid N,N'-bis(3-hydroxypropyl)diamide 生成 Diisopropyl-phosphoramidous acid 3-{4-[(E)-2-(4-{3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-propylcarbamoyl}-phenyl)-vinyl]-benzoylamino}-propyl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  从超交换到跳跃的交叉作为 DNA 发夹偶联物中光诱导电荷转移的机制

  摘要：

  已经在合成 DNA 发夹中研究了光致电荷分离和电荷重组的机制和动力学，该发夹具有由一到七个 A:T 碱基对分隔的供体和受体芪。飞秒宽带泵浦探针光谱、纳秒瞬态吸收光谱和皮秒荧光衰减测量的应用允许详细分析二苯乙烯受体单线态和电荷分离中间体的形成和衰减。当供体和受体被单个 A:T 碱基对分开时，电荷分离通过单步超交换机制发生。然而，当供体和受体被两个或多个 A:T 碱基对分开时，电荷分离会通过由空穴注入、空穴传输和空穴捕获组成的多步骤过程发生。在这种情况下，空穴到达电子供体比空穴注入桥接 A 束慢。电荷分离（空穴到达）和电荷复合的速率常数取决于供体-受体距离；然而，空穴注入的速率常数与施主-受主距离无关。从超交换到跳跃机制的交叉观察为 DNA 电子转移的分析提供了一个“缺失的环节”，需要重新评估 DNA 中光诱导电子转移的现有文献。空穴注入的速率常数与施主-受主距离无关。从超交换到跳跃机制的交叉观察为

  DOI：

  10.1021/ja0540831
• 作为产物：
  描述：

  cis-二苯乙烯-4,4'-二羧酸 在 氯化亚砜 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 生成 stilbene-4,4'-dicarboxylic acid N,N'-bis(3-hydroxypropyl)diamide
  参考文献：
  名称：

  Use of a Stilbenedicarboxamide Bridge in Stabilizing, Monitoring, and Photochemically Altering Folded Conformations of Oligonucleotides

  摘要：

  A stilbenedicarboxamide bridge (-Sigma-) is shown to serve as a unique and unusually effective cap for stabilizing and characterizing short oligonucleotide double and triple stranded structures. As representative of the stability of a family of oligomers studied, T-m values for the thermal transitions in 0.1 M NaCl of the hairpin forms of dTTT-Sigma-dAAA and dGCG-Sigma-dCGC are similar to 42 degrees C and >80 degrees C, respectively, and T-m for unfolding of the triple-stranded, double-hairpin conformation of d(TTTTTT-Sigma-)(2)dAAAAAA is 69 degrees C. The intercalating dye, ethidium, binds efficiently to the mini-hairpin structures formed by these conjugates, even to dTT-Sigma-dAA, which has a single four-nucleotide pocket; and the DNA groove binding agent, Hoechst 33258, interacts with dTTT-Sigma-dAAA as well as with longer conjugates. The distinctive monomer and excimer fluorescence bands for the stilbenedicarboxamide moiety provide useful information on the structures of these small organized domains, and photoinduced isomerization permits postsynthetic alteration of the geometry of the bridge and therefore alteration of the hybridization properties of the conjugate. The sensitivity to light depends on the nucleotides abutting the linker. When stability to light is desired, it can be achieved by incorporating a dG-dC pair in this position.

  DOI：

  10.1021/ja00133a005

文献信息

• Use of a Stilbenedicarboxamide Bridge in Stabilizing, Monitoring, and Photochemically Altering Folded Conformations of Oligonucleotides
  作者：Robert L. Letsinger、Taifeng Wu

  DOI：10.1021/ja00133a005

  日期：1995.7

  A stilbenedicarboxamide bridge (-Sigma-) is shown to serve as a unique and unusually effective cap for stabilizing and characterizing short oligonucleotide double and triple stranded structures. As representative of the stability of a family of oligomers studied, T-m values for the thermal transitions in 0.1 M NaCl of the hairpin forms of dTTT-Sigma-dAAA and dGCG-Sigma-dCGC are similar to 42 degrees C and >80 degrees C, respectively, and T-m for unfolding of the triple-stranded, double-hairpin conformation of d(TTTTTT-Sigma-)(2)dAAAAAA is 69 degrees C. The intercalating dye, ethidium, binds efficiently to the mini-hairpin structures formed by these conjugates, even to dTT-Sigma-dAA, which has a single four-nucleotide pocket; and the DNA groove binding agent, Hoechst 33258, interacts with dTTT-Sigma-dAAA as well as with longer conjugates. The distinctive monomer and excimer fluorescence bands for the stilbenedicarboxamide moiety provide useful information on the structures of these small organized domains, and photoinduced isomerization permits postsynthetic alteration of the geometry of the bridge and therefore alteration of the hybridization properties of the conjugate. The sensitivity to light depends on the nucleotides abutting the linker. When stability to light is desired, it can be achieved by incorporating a dG-dC pair in this position.
• Binding of Aminoglycoside Antibiotics with Modified A-site 16S rRNA Construct Containing Non-Nucleotide Linkers
  作者：Jeffrey B.-H. Tok、Wilson Wong、Nyla Baboolal

  DOI：10.1016/s0960-894x(01)00760-0

  日期：2002.2

  The design and synthesis of synthetically modified cyclic A-site 16S rRNA construct is reported. The binding characteristics of several members of the aminoglycoside antibiotics with this novel class of synthetically modified A-site 16S rRNA constructs were subsequently investigated. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Crossover from Superexchange to Hopping as the Mechanism for Photoinduced Charge Transfer in DNA Hairpin Conjugates
  作者：Frederick D. Lewis、Huihe Zhu、Pierre Daublain、Torsten Fiebig、Milen Raytchev、Qiang Wang、Vladimir Shafirovich

  DOI：10.1021/ja0540831

  日期：2006.1.1

  The mechanism and dynamics of photoinduced charge separation and charge recombination have been investigated in synthetic DNA hairpins possessing donor and acceptor stilbenes separated by one to seven A:T base pairs. The application of femtosecond broadband pump-probe spectroscopy, nanosecond transient absorption spectroscopy, and picosecond fluorescence decay measurements permits detailed analysis

  已经在合成 DNA 发夹中研究了光致电荷分离和电荷重组的机制和动力学，该发夹具有由一到七个 A:T 碱基对分隔的供体和受体芪。飞秒宽带泵浦探针光谱、纳秒瞬态吸收光谱和皮秒荧光衰减测量的应用允许详细分析二苯乙烯受体单线态和电荷分离中间体的形成和衰减。当供体和受体被单个 A:T 碱基对分开时，电荷分离通过单步超交换机制发生。然而，当供体和受体被两个或多个 A:T 碱基对分开时，电荷分离会通过由空穴注入、空穴传输和空穴捕获组成的多步骤过程发生。在这种情况下，空穴到达电子供体比空穴注入桥接 A 束慢。电荷分离（空穴到达）和电荷复合的速率常数取决于供体-受体距离；然而，空穴注入的速率常数与施主-受主距离无关。从超交换到跳跃机制的交叉观察为 DNA 电子转移的分析提供了一个“缺失的环节”，需要重新评估 DNA 中光诱导电子转移的现有文献。空穴注入的速率常数与施主-受主距离无关。从超交换到跳跃机制的交叉观察为