Ethyl 2-[2-[4-[(2-aminoacetyl)amino]phenyl]ethenyl]-4-hydroxybut-2-enoate

• 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: Ethyl 2-[2-[4-[(2-aminoacetyl)amino]phenyl]ethenyl]-4-hydroxybut-2-enoate
• 英文别名: ethyl 2-[2-[4-[(2-aminoacetyl)amino]phenyl]ethenyl]-4-hydroxybut-2-enoate
• 化学式: C₁₆H₂₀N₂O₄
• 分子量: 304.346
• InChiKey: UWKXDRMHELQSKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 2-[2-[4-[(2-aminoacetyl)amino]phenyl]ethenyl]-4-hydroxybut-2-enoate 在 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.33h， 生成 ethyl (E,E)-4-oxo-2-[4-(5,6-dihydro-11,12-didehydro-dibenzo[a,e]cyclooctenyl-5-oxcarbonylaminoacetamide)styryl]but-2-enoate
  参考文献：
  名称：

  A cascading reaction sequence involving ligand-directed azaelectrocyclization and autooxidation-induced fluorescence recovery enables visualization of target proteins on the surfaces of live cells

  摘要：

  设计用来诱导靶蛋白级联反应序列的通用探针已经成功合成。

  DOI：

  10.1039/c3ob42267d
• 作为产物：
  描述：

  ethyl (E,E)-2-[4-(N-tert-butoxycarbonyl-2-aminoacetamido)styryl]-4-(tetrahydro-2H-pyran-2-yloxy)but-2-enoate 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 Ethyl 2-[2-[4-[(2-aminoacetyl)amino]phenyl]ethenyl]-4-hydroxybut-2-enoate
  参考文献：
  名称：

  A cascading reaction sequence involving ligand-directed azaelectrocyclization and autooxidation-induced fluorescence recovery enables visualization of target proteins on the surfaces of live cells

  摘要：

  设计用来诱导靶蛋白级联反应序列的通用探针已经成功合成。

  DOI：

  10.1039/c3ob42267d

文献信息

• Development of bis-unsaturated ester aldehydes as amino-glue probes: sequential double azaelectrocyclization as a promising strategy for bioconjugation
  作者：Katsunori Tanaka、Yuka Nakamoto、Eric R. O. Siwu、Ambara R. Pradipta、Koji Morimoto、Takeshi Fujiwara、Suguru Yoshida、Takamitsu Hosoya、Yuki Tamura、Go Hirai、Mikiko Sodeoka、Koichi Fukase

  DOI：10.1039/c3ob41507d

  日期：——

  The unsaturated ester aldehyde, (E)-3-alkoxycarbonyl-5-phenyl-2,4-dienal, was efficiently dimerized by applying the strain-promoted double-click reaction with sym-dibenzo-1,5-cyclooctadiene-3,7-diyne. The resulting dimerized probe was sequentially reacted first with one peptide molecule and then with a protein or the amino groups on the surface of a live cell through double azaelectrocyclization to achieve highly efficient bioconjugation.

  (E)-3- 烷氧羰基-5-苯基-2,4-二烯醛是一种不饱和酯醛，通过与交联-二苯并-1,5-环辛二烯-3,7-二炔进行应变促进的双击反应，有效地将其二聚化。二聚后的探针先与一个肽分子发生反应，然后通过双氮电环化与蛋白质或活细胞表面的氨基发生反应，从而实现高效的生物共轭。
• JP6327547
  申请人：——

  公开号：——

  公开（公告）日：——
• Highly reactive “RIKEN click” probe for glycoconjugation on lysines
  作者：Regina Sibgatullina、Katsumasa Fujiki、Takefumi Murase、Takahiro Yamamoto、Taiji Shimoda、Almira Kurbangalieva、Katsunori Tanaka

  DOI：10.1016/j.tetlet.2017.03.081

  日期：2017.5

  One pot double click strategy containing strain-promoted click-reaction followed by 67-c-azaelectrocyclization (RIKEN click reaction) has worked well in the synthesis of multivalent homogeneous and heterogeneous N-glycoalbumins. We have slightly changed the structure of linker unsaturated aldehyde used in this method. As a result it can be easily synthesized from commercially available material and furthermore, the enhancement of its reactivity towards both click-reactions was observed. The data described in this Communications facilitate the usage of the double click strategy as a general method for the synthesis of a variety of neo-N-glycoproteins. (C) 2017 Elsevier Ltd. All rights reserved.
• A cascading reaction sequence involving ligand-directed azaelectrocyclization and autooxidation-induced fluorescence recovery enables visualization of target proteins on the surfaces of live cells
  作者：Katsunori Tanaka、Masataka Kitadani、Ayumi Tsutsui、Ambara R. Pradipta、Rie Imamaki、Shinobu Kitazume、Naoyuki Taniguchi、Koichi Fukase

  DOI：10.1039/c3ob42267d

  日期：——

  A general probe designed to induce a cascading sequence of reactions on a target protein was efficiently synthesized.

  设计用来诱导靶蛋白级联反应序列的通用探针已经成功合成。