[6-(2-氨基乙基)-1H-吲哚-3-基]乙酸 | 852615-34-0

• 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
• 中文名称: [6-(2-氨基乙基)-1H-吲哚-3-基]乙酸
• 英文名称: 6-(2-aminoethyl)indole-3-acetic acid
• 英文别名: 2-(6-(2-aminoethyl)-1H-indol-3-yl)acetic acid；2-[6-(2-aminoethyl)-1H-indol-3-yl]acetic acid
• CAS: 852615-34-0
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: HNXJOSSHZREKSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  79.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [6-(2-氨基乙基)-1H-吲哚-3-基]乙酸 、 生物素化-epsilon-氨基己酸-N-羟基丁二酰亚胺活化酯 在 N-甲基吗啉 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以29.1 mg的产率得到6-{2-[6-(biotinamido)hexanamido]ethyl}indole-3-acetic acid
  参考文献：
  名称：

  Aminoethyl-substituted indole-3-acetic acids for the preparation of tagged and carrier-linked auxin

  摘要：

  Indole-3-acetic acid is an indispensable hormone (auxin) in plants and an important metabolite in humans, animals, and microorganisms. Here we introduce its 5- and 6-(2-aminoethyl)-derivatives for use in the design of novel research tools, such as immobilized and carrier-linked forms of indole-3-acetic acid and its conjugates with biochemical tags or biocompatible molecular probes. The aliphatic nitrogens of 5- and 6-(2-aminoethyl)indole were acetylated and the products were converted to the corresponding 3-(N,N-dimethylamino)methyl derivatives (gramines). These were reacted with cyanide. Saponification of the resulting acetonitriles was accompanied by N-deprotection to yield 5- and 6-(2-aminoethyl)indole-3-acetic acids. The latter were chemically stable and could be linked, via their amino groups, and without prior protection of their carboxyl moieties, to bovine serum albumin and to biotin, including appropriate spacer modules. One of the protein conjugates was used to elicit the formation of monoclonal antibodies, which were evaluated using the biotin conjugates in an enzyme-linked immunosorbent assay employing streptavidin-coupled alkaline phosphatase, and thus shown to recognize predominantly the indole-3-acetic acid moiety. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.046

文献信息

• Aminoethyl-substituted indole-3-acetic acids for the preparation of tagged and carrier-linked auxin
  作者：Nebojša Ilić、Ivan Habuš、Lana S. Barkawi、Seijin Park、Zoran Štefanić、Biserka Kojić-Prodić、Jerry D. Cohen、Volker Magnus

  DOI：10.1016/j.bmc.2005.02.046

  日期：2005.5

  Indole-3-acetic acid is an indispensable hormone (auxin) in plants and an important metabolite in humans, animals, and microorganisms. Here we introduce its 5- and 6-(2-aminoethyl)-derivatives for use in the design of novel research tools, such as immobilized and carrier-linked forms of indole-3-acetic acid and its conjugates with biochemical tags or biocompatible molecular probes. The aliphatic nitrogens of 5- and 6-(2-aminoethyl)indole were acetylated and the products were converted to the corresponding 3-(N,N-dimethylamino)methyl derivatives (gramines). These were reacted with cyanide. Saponification of the resulting acetonitriles was accompanied by N-deprotection to yield 5- and 6-(2-aminoethyl)indole-3-acetic acids. The latter were chemically stable and could be linked, via their amino groups, and without prior protection of their carboxyl moieties, to bovine serum albumin and to biotin, including appropriate spacer modules. One of the protein conjugates was used to elicit the formation of monoclonal antibodies, which were evaluated using the biotin conjugates in an enzyme-linked immunosorbent assay employing streptavidin-coupled alkaline phosphatase, and thus shown to recognize predominantly the indole-3-acetic acid moiety. (c) 2005 Elsevier Ltd. All rights reserved.