(S)-2-amino-3-(6-(3-(trifluoromethyl)-3H-diazirin-3-yl)-1H-indol-3-yl)propanoic acid | 1400883-45-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-2-amino-3-(6-(3-(trifluoromethyl)-3H-diazirin-3-yl)-1H-indol-3-yl)propanoic acid
• 英文别名: (2S)-2-amino-3-[6-[3-(trifluoromethyl)diazirin-3-yl]-1H-indol-3-yl]propanoic acid
• CAS: 1400883-45-5
• 化学式: C₁₃H₁₁F₃N₄O₂
• 分子量: 312.251
• InChiKey: CWUXDIGEUQCGKJ-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-2-amino-3-(6-(3-(trifluoromethyl)-3H-diazirin-3-yl)-1H-indol-3-yl)propanoic acid 在 溶剂黄146 作用下， 以 甲醇 、 苯 为溶剂， 反应 1.5h， 生成 methyl (2S)-2-acetamido-3-[6-[3-(trifluoromethyl)diazirin-3-yl]-1H-indol-3-yl]propanoate
  参考文献：
  名称：

  L-Phototryptophan

  摘要：

  AbstractPhototryptophan is a new photoactivatable amino acid designed to be incorporated into tryptophan‐containing peptides for photoaffinity labeling. The synthesis of phototryptophan starts from 6‐bromoindole with the installation of an 1‐azi‐2,2,2‐trifluoroethyl moiety, followed by microwave‐assisted condensation with serine under mild conditions. Separation of the N‐acetylated enantiomers was possible by employing Aspergillus aminoacylase. Differential scanning calorimetry showed that phototryptophan is thermally stable up to 100 °C. Boc‐L‐Phototryptophan was used to assemble a diazirine analog of the marine natural product hemiasterlin.

  DOI：

  10.1002/ejoc.201201726
• 作为产物：
  描述：

  1-(tert-butyldimethylsilyl)-6-(3-(trifluoromethyl)diaziridin-3-yl)-1H-indole 在 cobalt(II) chloride hexahydrate 、 aminoacylase from Aspergillus genus 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 aq. phosphate buffer 、 水 为溶剂， 反应 18.5h， 生成 (S)-2-amino-3-(6-(3-(trifluoromethyl)-3H-diazirin-3-yl)-1H-indol-3-yl)propanoic acid
  参考文献：
  名称：

  L-Phototryptophan

  摘要：

  AbstractPhototryptophan is a new photoactivatable amino acid designed to be incorporated into tryptophan‐containing peptides for photoaffinity labeling. The synthesis of phototryptophan starts from 6‐bromoindole with the installation of an 1‐azi‐2,2,2‐trifluoroethyl moiety, followed by microwave‐assisted condensation with serine under mild conditions. Separation of the N‐acetylated enantiomers was possible by employing Aspergillus aminoacylase. Differential scanning calorimetry showed that phototryptophan is thermally stable up to 100 °C. Boc‐L‐Phototryptophan was used to assemble a diazirine analog of the marine natural product hemiasterlin.

  DOI：

  10.1002/ejoc.201201726

文献信息

• Comprehensive Synthesis of Photoreactive (3-Trifluoromethyl)diazirinyl Indole Derivatives from 5- and 6- Trifluoroacetylindoles for Photoaffinity Labeling
  作者：Yuta Murai、Katsuyoshi Masuda、Yasuko Sakihama、Yasuyuki Hashidoko、Yasumaru Hatanaka、Makoto Hashimoto

  DOI：10.1021/jo301552m

  日期：2012.10.5

  5- and 6-trifluoromethyldiazirinyl indoles were synthesized from corresponding bromoindole derivatives for the first time. They acted as mother skeletons for the comprehensive synthesis of various bioactive indole metabolites. These can be used in biological functional analysis as diazirine-based photoaffinity labels.

  首次从相应的溴吲哚衍生物合成了5-和6-三氟甲基二叠氮基吲哚。它们充当了各种生物活性吲哚代谢产物的综合合成的母体骨架。这些可以在生物功能分析中用作基于二嗪啉的光亲和标记。