Proviolacein

• 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: Proviolacein
• 英文别名: 5-(5-hydroxy-1H-indol-3-yl)-3-(1H-indol-3-yl)pyrrol-2-one
• 化学式: C₂₀H₁₃N₃O₂
• 分子量: 327.3
• InChiKey: AEUPUFUMWGIQGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  氢(+1)阳离子 、 氧气 、 Protoviolaceinate 生成 二氧化碳 、 水 、 Proviolacein
  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

• Violacein and related tryptophan metabolites produced by Chromobacterium violaceum: biosynthetic mechanism and pathway for construction of violacein core
  作者：Tsutomu Hoshino

  DOI：10.1007/s00253-011-3468-z

  日期：2011.9

  All three oxygen atoms in the violacein core are derived from molecular oxygen. The most interesting biosynthetic mechanism is the 1,2-shift of the indole nucleus on the left side of the violacein scaffold. The alternative Trp molecule is directly incorporated into the right side of the violacein core. This indole shift has been observed only in violacein biosynthesis, despite the large number of natural

  紫罗兰素是由几种革兰氏阴性细菌产生的天然紫罗兰色颜料，包括紫罗兰杆菌，淡紫色詹氏菌和杜氏假单胞菌D2等。这种颜料具有潜在的医学应用，例如抗菌，抗锥虫，抗溃疡和抗癌药。堇青素的结构由三个单元组成：5-羟基吲哚，羟吲哚和2-吡咯烷酮。吡咯烷酮核中氢，氮和碳的生物合成来源是通过使用各种稳定的同位素标记色氨酸（Trps）进行饲养实验确定的。CH（2）在Trp的3位置的Pro-S氢在生物合成过程中被保留。氮原子仅来自α-氨基，骨架碳原子源自两个Trp分子的侧链。紫胶素核心中的所有三个氧原子均来自分子氧。最有趣的生物合成机制是在紫胶素支架左侧的吲哚核的1,2-移位。替代的Trp分子直接并入紫胶素核心的右侧。尽管已经分离了大量天然产物，但仅在紫堇青素生物合成中才观察到这种吲哚转移。2006年至2008年，生物合成研究取得了显着进展。在这三年中，大多数中间体和完整的途径得以建立。涉及两个独立的过程：由五种
• RECOMBINANT MICROORGANISM HAVING INCREASED ABILITY TO PRODUCE HYDROPHOBIC MATERIAL AND CELL-MEMBRANE ENGINEERING METHOD FOR PREPARATION THEREOF
  申请人：Korea Advanced Institute of Science and Technology

  公开号：EP4001406A2

  公开（公告）日：2022-05-25

  Disclosed are a recombinant microorganism for producing a hydrophobic material, which is subjected to cell-membrane engineering in order to be imparted with at least one characteristic among an increase in a cell-membrane area, an increase in formation and secretion of an outer membrane vesicle, and an increase in formation of an inner membrane vesicle, and a cell-membrane engineering method for preparation thereof, whereby an insoluble hydrophobic material can be produced with high efficiency, the recombinant microorganism for high-efficiency production of carotenoids or violacein analogues is useful for producing natural pigments, antioxidants, antibiotics, cosmetic additives, anticancer agents, food additives, or nutritional supplements, and the natural pigment production technology developed herein achieves a great increase in production ability. Therefore, the present invention is effective at preparing a recombinant strain for efficient production of a variety of industrially and medically useful metabolites and at establishing an efficient preparation method.

  本发明公开了一种用于生产疏水材料的重组微生物，对其进行细胞膜工程学处理，以赋予其细胞膜面积增加、外膜囊泡形成和分泌增加、内膜囊泡形成增加中的至少一种特性，以及制备该微生物的细胞膜工程学方法、据此可高效生产不溶性疏水材料，高效生产类胡萝卜素或紫草素类似物的重组微生物可用于生产天然色素、抗氧化剂、抗生素、化妆品添加剂、抗癌剂、食品添加剂或营养补充剂，本发明开发的天然色素生产技术实现了生产能力的大幅提高。因此，本发明能有效制备重组菌株，高效生产多种工业和医学上有用的代谢物，并建立高效的制备方法。
• Processes and host cells for genome, pathway, and biomolecular engineering
  申请人：enEvolv, Inc.

  公开号：US10370654B2

  公开（公告）日：2019-08-06

  The present disclosure provides compositions and methods for genomic engineering.

  本公开提供了基因组工程的组合物和方法。
• Cell-free biomolecular breadboards and related methods and arrangements
  申请人：CALIFORNIA INSTITUTE OF TECHNOLOGY

  公开号：US11004536B2

  公开（公告）日：2021-05-11

  Provided herein are methods and arrangements and related cell-free biomolecular breadboards configured to design, build, implement, debug, and/or test a genetic circuit to be operated in a target environment, by testing in a cell-free system under conditions of the target environment, molecular components of the genetic circuit and/or combinations thereof to select the molecular components and/or combinations thereof of a genetic circuit operative in the target environment.

  本文提供的方法和安排以及相关的无细胞生物分子面包板被配置用于设计、构建、实现、调试和/或测试在目标环境中运行的基因电路，方法是在目标环境条件下在无细胞系统中测试基因电路的分子元件和/或其组合，以选择在目标环境中运行的基因电路的分子元件和/或其组合。
• 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.