N-{3-[(tert-butoxycarbonyl)amino]propanoyl}-N-hydroxy-β-alanine | 136413-25-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-{3-[(tert-butoxycarbonyl)amino]propanoyl}-N-hydroxy-β-alanine
• CAS: 136413-25-7
• 化学式: C₁₈H₂₆N₂O₆
• 分子量: 366.414
• InChiKey: BZMFXYZBRCQOEJ-UHFFFAOYSA-N

物化性质

• 密度：
  1.201±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105.17
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-{3-[(tert-butoxycarbonyl)amino]propanoyl}-N-hydroxy-β-alanine 在 盐酸 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  用于 68Ga 核成像的去铁胺 E 铁载体的环状类似物：金黄色葡萄球菌的配位化学和生物活性

  摘要：

  由于耐多药细菌是一个新出现的问题和对人类的威胁，因此积极寻求新的治疗和诊断策略。我们的目标是利用铁载体（由微生物产生的铁特异性强螯合剂）作为镓离子载体进行诊断，应用 Fe(III) 可以成功地被 G​​a(III) 取代而不会失去所研究复合物的生物学特性，这使得分子通过正电子发射断层扫描（PET）成像。在这里，我们报告合成、全溶液化学、热力学表征和去铁胺 E (FOXE) 铁载体的仿生衍生物 (FOX) 的初步生物学评估，用68 Ga 放射性标记可能在金黄色葡萄球菌的 PET 成像中应用. 从一系列六种仿生类似物（与 FOXE 的循环长度和异羟肟酸和酰胺基团的位置不同）中，确定了大多数 FOXE 类似化合物 - FOX 2-4 和 FOX 的最高 Fe(III) 和 Ga(III) 稳定性2-5; 我们还建立了 Ga-FOXE 复合物的稳定常数。为此，使用了光谱和电位滴定以及 Fe(III)-Ga(III)

  DOI：

  10.1021/acs.inorgchem.1c02453
• 作为产物：
  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

文献信息

• Katoh, Akira; Akiyama, Masayasu, Journal of the Chemical Society. Perkin transactions I, 1991, # 8, p. 1839 - 1842
  作者：Katoh, Akira、Akiyama, Masayasu

  DOI：——

  日期：——