(3E)-3-[5-(1H-indol-3-yl)-2-oxo-1H-pyrrol-3-ylidene]-1H-indol-2-one

• 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: (3E)-3-[5-(1H-indol-3-yl)-2-oxo-1H-pyrrol-3-ylidene]-1H-indol-2-one
• 化学式: C₂₀H₁₃N₃O₂
• 分子量: 327.3
• InChiKey: OJUJNNKCVPCATE-QGOAFFKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  Deoxyviolaceinate 、 氢(+1)阳离子 、 氧气 生成 二氧化碳 、 (3E)-3-[5-(1H-indol-3-yl)-2-oxo-1H-pyrrol-3-ylidene]-1H-indol-2-one 、 水
  参考文献：
  名称：

  Biosynthesis of violacein: a genuine intermediate, protoviolaceinic acid, produced by VioABDE, and insight into VioC function

  摘要：

  由 VioABDE 混合酶产生的一种紫草素生物合成中间体被阐明为 5-(5-羟基-1H-吲哚-3-基)-3-(1H-吲哚-3-基)-1H-吡咯-2-羧酸，命名为原紫草素酸，表明负责最后生物合成步骤的 VioC、负责最后的生物合成步骤，在右侧吲哚环的 2 位进行氧合，氧合反应以非酶方式形成中央吡咯烷酮核心。

  DOI：

  10.1039/b705358d

文献信息

• Biosynthesis of violacein: a genuine intermediate, protoviolaceinic acid, produced by VioABDE, and insight into VioC function
  作者：Kouhei Shinoda、Takuji Hasegawa、Hiroaki Sato、Masaaki Shinozaki、Hirotomo Kuramoto、Yosuke Takamiya、Tsutomu Sato、Naoki Nikaidou、Takeshi Watanabe、Tsutomu Hoshino

  DOI：10.1039/b705358d

  日期：——

  A biosynthetic intermediate of violacein produced by the mixed enzymes of VioABDE was elucidated to be 5-(5-hydroxy-1H-indol-3-yl)-3-(1H-indol-3-yl)-1H-pyrrole-2-carboxylic acid, named protoviolaceinic acid, indicating that VioC, responsible for the final biosynthetic step, works to oxygenate at the 2-position of the right side indole ring, and that the oxygenation reaction to form the central pyrrolidone core proceeds in a non-enzymatic fashion.

  由 VioABDE 混合酶产生的一种紫草素生物合成中间体被阐明为 5-(5-羟基-1H-吲哚-3-基)-3-(1H-吲哚-3-基)-1H-吡咯-2-羧酸，命名为原紫草素酸，表明负责最后生物合成步骤的 VioC、负责最后的生物合成步骤，在右侧吲哚环的 2 位进行氧合，氧合反应以非酶方式形成中央吡咯烷酮核心。
• Chromobacterium bioactive compositions and metabolites
  申请人：Marrone Bio Innovations, Inc.

  公开号：US10405555B2

  公开（公告）日：2019-09-10

  Provided are bioactive compounds and metabolites derived from Chromobacterium species culture responsible for controlling pests, compositions containing these compounds, methods for obtaining these compounds and methods of using these compounds and compositions for controlling pests.

  本文提供了从负责控制害虫的色杆菌培养物中提取的生物活性化合物和代谢物、含有这些化合物的组合物、获得这些化合物的方法以及使用这些化合物和组合物控制害虫的方法。
• In Vitro Biosynthesis of Violacein from <scp>l</scp>-Tryptophan by the Enzymes VioA−E from <i>Chromobacterium violaceum</i>
  作者：Carl J. Balibar、Christopher T. Walsh

  DOI：10.1021/bi061998z

  日期：2006.12.1

  The purple chromobacterial pigment violacein arises by enzymatic oxidation and coupling of two molecules of L-tryptophan to give a rearranged pyrrolidone-containing scaffold in the final pigment. We have purified five contiguously encoded proteins VioA-E after expression in Escherichia coli and demonstrate the full 14-electron oxidation pathway to yield the final chromophore. The flavoenzyme VioA and the heme protein VioB work in conjunction to oxidize and dimerize L-tryptophan to a nascent product that can default to the off pathway metabolite chromopyrrolic acid. In the presence of VioE, the intermediate instead undergoes on-pathway [1,2] indole rearrangement to prodeoxyviolacein. The last two enzymes in the pathway are flavin-dependent oxygenases, VioC and VioD, that act sequentially. VioD hydroxylates one indole ring at the 5-position to yield proviolacein, and VioC then acts on the other indole ring at the 2-position to create the oxindole and complete violacein formation.
• CHROMAMIDE A (1), COMPOSITIONS COMPRISING CHROMAMIDE A (1) WITH INSECTICIDAL ACTIVITY
  申请人：Marrone Bio Innovations, Inc.

  公开号：EP2632272B1

  公开（公告）日：2019-08-21
• CHROMOBACTERIUM FORMULATIONS, COMPOSTIONS, METABOLITES AND THEIR USES
  申请人：Marrone Bio Innovations, Inc.

  公开号：EP2770836B1

  公开（公告）日：2018-08-08