ethyl 3-((benzyloxy){3-[(tert-butoxycarbonyl)amino]propanoyl}amino)propanoate | 190261-48-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 3-((benzyloxy){3-[(tert-butoxycarbonyl)amino]propanoyl}amino)propanoate
• CAS: 190261-48-4
• 化学式: C₂₀H₃₀N₂O₆
• 分子量: 394.468
• InChiKey: MHNICNUUGSLQPI-UHFFFAOYSA-N

物化性质

• 密度：
  1.137±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  28.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  94.17
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-((benzyloxy){3-[(tert-butoxycarbonyl)amino]propanoyl}amino)propanoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以96%的产率得到N-{3-[(tert-butoxycarbonyl)amino]propanoyl}-N-hydroxy-β-alanine
  参考文献：
  名称：

  Ferrioxamine B Analogues:  Targeting the FoxA Uptake System in the Pathogenic Yersinia enterocolitica

  摘要：

  A series of ferrioxamine 6 analogues that target the bacterium Yersinia enterocolitica were prepared. These iron carriers are composed of three hydroxamate-containing monomeric units. Two identical monomers consist of N-hydroxy-3-aminopropionic acid coupled with beta-alanine, and a third unit at the amino terminal is composed of N-hydroxy-3-aminopropionic acid and one of the following amino acids: beta-alanine (1a), phenylalanine (1b), cyclohexylalanine (1c), or glycine (1d). Thermodynamic results for representatives of the analogues have shown a strong destabilization (3-4 orders of magnitude) of the ferric complexes with respect to ferrioxamine B, probably due to shorter spacers and a more strained structure around the metal center. No significant effect of the variations at the N-terminal has been observed on the stability of the ferric complexes. By contrast, using in vivo radioactive uptake experiments, we have found that these modifications have a substantial effect on the mechanism of iron(Ill) uptake in the pathogenic bacteria Yersinia enterocolitica. Analogues la and 1d were utilized by the ferrioxamine B uptake system (FoxA), while 1b and 1c either used different uptake systems or were transported to the microbial cell nonspecifically by diffusion via the cell membrane. Transport via the FoxA system was also confirmed by uptake experiments with the FoxA deficient strain of Yersinia enterocolitica. A fluorescent marker, attached to 1a in a way that did not interfere with its biological activity, provided additional means to monitor the uptake mechanism by fluorescence techniques. Of particular interest is the observation that 1a was utilized by the uptake system of ferrioxamine B in Yersinia enterocolitica (FoxA) but failed to use the ferrioxamine uptake route in Pseudomonas putida. Here, we present a case in which biomimetic siderophore analogues deliberately designed for a particular bacterium can distinguish between related uptake systems of different microorganisms.

  DOI：

  10.1021/ja035182m
• 作为产物：
  描述：

  Boc-beta-丙氨酸 、 ethyl 3-((benzyloxy)amino)propanoate 在 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 作用下， 以 乙腈 为溶剂， 生成 ethyl 3-((benzyloxy){3-[(tert-butoxycarbonyl)amino]propanoyl}amino)propanoate
  参考文献：
  名称：

  分子键盘锁：一种能够授权密码输入的光化学设备

  摘要：

  本文描述了在分子尺度上保护信息的新概念。通过利用分子布尔逻辑的原理，我们设计了一种模拟电子键盘锁操作的分子装置，例如，用于多种应用的通用安全电路，其中对对象或数据的访问仅限于人数有限。这种锁与简单分子逻辑门的区别在于，它的输出信号不仅取决于输入的正确组合，还取决于引入这些输入的正确顺序。换句话说，人们需要知道打开这把锁的确切密码。不同的密码输入由两种化学和一种光学输入信号的组合编码，可以分别激活，芘或荧光素荧光团的蓝色或绿色荧光输出通道。每个通道中的信息是一个单比特光输出信号，可用于授权用户、验证产品的身份验证或启动更高的过程。这一发展不仅为一类新的分子决策设备开辟了道路，而且还为现有的防御技术（如密码学和隐写术）增加了新的保护维度，这些技术以前是用分子实现的。

  DOI：

  10.1021/ja065317z