(Z)-4-((4-((tert-butoxycarbonyl)amino)butyl)amino)-4-oxobut-2-enoic acid | 1392330-39-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-4-((4-((tert-butoxycarbonyl)amino)butyl)amino)-4-oxobut-2-enoic acid
• 英文别名: N-(4-tert-butoxycarbonylaminobutyl)maleamic acid
• CAS: 1392330-39-0
• 化学式: C₁₃H₂₂N₂O₅
• 分子量: 286.328
• InChiKey: POMZIXZUUYWBPC-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.05
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  104.73
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (Z)-4-((4-((tert-butoxycarbonyl)amino)butyl)amino)-4-oxobut-2-enoic acid 在 sodium acetate 、 乙酸酐 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以0.42 g的产率得到tert-butyl (4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butyl)carbamate
  参考文献：
  名称：

  Synthesis and characterization of a new polymer–drug conjugate with pH-induced activity

  摘要：

  A well-defined, stimuli-responsive tetrapolymer with pH-responsive characteristics and targeting specificity has been synthesized by radical copolymerization of methacrylic acid. N-(2-hydroxypropyl)methacrylamide, methacryloyl glycylglycyl sulfamethoxazole, and N-(methacryloyl)glycylglycine 4-nitrophenyl ester. The structure and properties of tetrapolymer were investigated by NMR, FT-IR, UV-visible absorption, TEM and gel permeation chromatography. Incorporation of maleimide linker into tetrapolymer facilitates its conjugation with antibody fragments, as demonstrated by the solid-phase immunoassay experiments. The TEM image shows that tetrapolymer had self-assembled a spherical micelle with a diameter ranging from 50 to 150 nm. Altering the pH of the solution leads to a different extent of aggregation at pH 6.5-3.5, responding in accordance with the properties associated with the extracellular environment of solid tumors and endocytosis. Furthermore, fluorescence spectroscopy indicated a critical micelle concentration (CMC) of 1 mg/mL. Because of the solvation and ionization effects, the tetrapolymer showed considerably enhanced antibacterial activities against Escherichia coli in the presence of DMSO and the antibacterial activity increased with decreasing pH value. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2012.06.006
• 作为产物：
  描述：

  二碳酸二叔丁酯 以 二氯甲烷 、 丙酮 为溶剂， 反应 18.0h， 生成 (Z)-4-((4-((tert-butoxycarbonyl)amino)butyl)amino)-4-oxobut-2-enoic acid
  参考文献：
  名称：

  Synthesis and characterization of a new polymer–drug conjugate with pH-induced activity

  摘要：

  A well-defined, stimuli-responsive tetrapolymer with pH-responsive characteristics and targeting specificity has been synthesized by radical copolymerization of methacrylic acid. N-(2-hydroxypropyl)methacrylamide, methacryloyl glycylglycyl sulfamethoxazole, and N-(methacryloyl)glycylglycine 4-nitrophenyl ester. The structure and properties of tetrapolymer were investigated by NMR, FT-IR, UV-visible absorption, TEM and gel permeation chromatography. Incorporation of maleimide linker into tetrapolymer facilitates its conjugation with antibody fragments, as demonstrated by the solid-phase immunoassay experiments. The TEM image shows that tetrapolymer had self-assembled a spherical micelle with a diameter ranging from 50 to 150 nm. Altering the pH of the solution leads to a different extent of aggregation at pH 6.5-3.5, responding in accordance with the properties associated with the extracellular environment of solid tumors and endocytosis. Furthermore, fluorescence spectroscopy indicated a critical micelle concentration (CMC) of 1 mg/mL. Because of the solvation and ionization effects, the tetrapolymer showed considerably enhanced antibacterial activities against Escherichia coli in the presence of DMSO and the antibacterial activity increased with decreasing pH value. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2012.06.006

文献信息

• Synthesis of azobenzenealkylmaleimide probes to photocontrol the enzyme activity of a bacterial histone deacetylase-like amidohydrolase
  作者：Benjamin Horstmann、Michael Korbus、Tatjana Friedmann、Christiane Wolff、Christina Marie Thiele、Franz-Josef Meyer-Almes

  DOI：10.1016/j.bioorg.2014.10.004

  日期：2014.12

  A series of azobenzenealkylmaleimides (AMDs) with different spacer length was synthesized and coupled via Michael-Addition to a specific mutant of a bacterial histone deacetylase-like amidohydrolase (HDAH). Michaelis-Menten parameters (V-max and K-m) were employed to characterize the effect of both, the spacer length and the configuration (cis vs. trans) of the attached azobenzene moiety, on the HDAH enzyme activity. The photoswitch behavior of the AMD/enzyme conjugate activity was clearly influenced by the AMD spacer length. This study highlights the importance of steric rearrangement of the photoswitch with respect to the active site and describes a strategy to optimize the photocontrol of HDAH. (C) 2014 Elsevier Inc. All rights reserved.