(E)-3-indolyl-acetaldoxime | 95394-24-4

• 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: (E)-3-indolyl-acetaldoxime
• 英文别名: (E)-3-Indolylacetaldoxime；indole-3-acetaldoxime；(E)-indol-3-ylacetaldoxime；(NE)-N-[2-(1H-indol-3-yl)ethylidene]hydroxylamine
• CAS: 95394-24-4
• 化学式: C₁₀H₁₀N₂O
• 分子量: 174.202
• InChiKey: ZLIGRGHTISHYNH-WUXMJOGZSA-N

物化性质

• 沸点：
  426.0±28.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  48.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-indolyl-acetaldoxime 生成 吲哚-3-乙腈 、 水
  参考文献：
  名称：

  Arabidopsis Cytochrome P450 Monooxygenase 71A13 Catalyzes the Conversion of Indole-3-Acetaldoxime in Camalexin Synthesis

  摘要：

  卡马莱辛（3-噻唑-2-基吲哚）是由拟南芥产生的吲哚生物碱植物抗菌素，被认为对抵抗坏死性真菌病原体（如十字花科黑轮纹菌和灰霉菌）很重要。它是由色氨酸产生的，色氨酸通过细胞色素P450单氧酶CYP79B2和CYP79B3的作用转化为吲哚乙醛肟（IAOx）。其余的生物合成步骤尚不清楚，只有最后一步是由CYP71B15（PAD3）将二氢卡马莱辛酸转化为卡马莱辛。本文报道了CYP71A13的特性。携带cyp71A13突变的植物在感染烟草青霉病菌或十字花科黑轮纹菌后产生的卡马莱辛大大减少，并且易感于十字花科黑轮纹菌，与pad3和cyp79B2 cyp79B3突变体一样。CYP71A13和PAD3的表达水平是共调节的。在大肠杆菌中表达的CYP71A13将IAOx转化为吲哚-3-乙腈（IAN）。在烟草中表达CYP79B2和CYP71A13导致色氨酸转化为IAN。外源供应的IAN恢复了cyp71A13突变体植物中的卡马莱辛产生。综上所述，这些结果表明CYP71A13催化卡马莱辛合成中IAOx到IAN的转化，并进一步支持卡马莱辛在抵抗十字花科黑轮纹菌中的作用。

  DOI：

  10.1105/tpc.107.051383
• 作为产物：
  描述：

  3-(2-硝基乙基)吲哚 在 三乙胺 作用下， 以 丙酮 为溶剂， 反应 3.5h， 以41%的产率得到(E)-3-indolyl-acetaldoxime
  参考文献：
  名称：

  Photochemical Conversion of Aliphatic Nitro Compounds into Oximes

  摘要：

  在三乙胺存在下，通过在丙酮中照射，脂肪族硝基化合物转化为肟，产率适中。

  DOI：

  10.1055/s-1989-27199

文献信息

• Indolyl-3-acetaldoxime dehydratase from the phytopathogenic fungus Sclerotinia sclerotiorum: Purification, characterization, and substrate specificity
  作者：M. Soledade C. Pedras、Zoran Minic、Premila D. Thongbam、Vangala Bhaskar、Sabine Montaut

  DOI：10.1016/j.phytochem.2010.10.002

  日期：2010.12

  acid sequence of IAD, determined using LC-ESI-MS/MS, identified it as the protein SS1G_01653 from S. sclerotiorum. IADSs was highly homologous (84% amino acid identity) to the hypothetical protein BC1G_14775 from Botryotinia fuckeliana B05.10. In addition, similarity to the phenylacetaldoxime dehydratases from Gibberella zeae (33% amino acid identity) and Bacillus sp. (20% amino acid identity) was noted

  描述了由植物真菌病原体核盘菌产生的吲哚基-3-乙醛肟脱水酶的纯化和表征。底物特异性表明它是一种吲哚基-3-乙醛肟脱水酶（IAD，EC 4.99.1.6），可催化吲哚基-3-乙醛肟转化为吲哚基-3-乙腈。该酶显示出 Michaelis-Menten 动力学，表观分子量为 44 kDa。使用 LC-ESI-MS/MS 确定 IAD 的氨基酸序列，将其鉴定为来自核盘菌的蛋白质 SS1G_01653。IADS 与来自 Botryotinia fuckeliana B05.10 的假设蛋白 BC1G_14775 高度同源（84% 氨基酸同一性）。此外，与来自玉米赤霉（33% 氨基酸同一性）和芽孢杆菌的苯乙醛肟脱水酶相似。注意到（20% 氨基酸同一性）。在厌氧条件下加入 Na(2)S(2)O(4) 后，IADSs 的比活性增加了约 17 倍，但在没有 Na(2)S(2)O(4) 的情况下没有显着变化观
• Biosynthetic Engineering of Glucosinolates
  申请人：Geu-Flores Fernando

  公开号：US20110016582A1

  公开（公告）日：2011-01-20

  The invention provides methods and materials, such as newly characterised genes, and novel processes, for converting a host from a phenotype whereby the host is unable to carry out glucosinolate (GSL) biosynthesis or chain elongation from an amino acid GSL-precursor to a phenotype whereby the host carries out said biosynthesis or elongation.

  本发明提供了一种将宿主从无法进行葡萄糖硫酸盐（GSL）生物合成或链延伸的表型转化为能够进行上述生物合成或延伸的表型的方法和材料，例如新鉴定的基因和新型工艺。
• P450 Monooxygenases of the cyp79 family
  申请人：——

  公开号：US20030166202A1

  公开（公告）日：2003-09-04

  The invention provides DNA coding for cytochrome P450 monooxygenases of the CYP79 family catalyzing the conversion of an aliphatic or aromatic amino acid or chain-elongated methionine homologue to the corresponding oxime. Preferred embodiments of the invention are enzymes catalyzing the conversion of L-Valine and L-Isoleucine such as the cassava enzymes CYP79D1 and CYP79D2, enzymes catalyzing the conversion of tyrosine such as the Triglochin maritima enzymes CYP79E1 and CYP79E2, enzymes catalyzing the conversion of tryptophan to the corresponding oxime indole-3-acetaldoxime such as the Arabidopsis thaliana enzyme CYP79A2 and the Brassica napus enzyme CYP79B5, and enzymes catalyzing the conversion of a chain-elongated methionine homologue such as the Arabidopsis thaliana enzymes CYP79F1 and CYP79F2. Transgenic expression of said DNA or parts thereof in plants can be used to manipulate the biosynthesis of corresponding glucosinolates or cyanogenic glucosides.

  该发明提供了编码CYP79家族细胞色素P450单加氧酶的DNA，其催化将脂肪族或芳香族氨基酸或链延长的蛋氨酸同源物转化为相应的肟类。该发明的优选实施例是催化L-缬氨酸和L-异亮氨酸转化的酶，例如木薯酶CYP79D1和CYP79D2，催化酪氨酸转化的Triglochin maritima酶CYP79E1和CYP79E2，催化色氨酸转化为相应的肟类吲哚-3-乙醛肟的Arabidopsis thaliana酶CYP79A2和Brassica napus酶CYP79B5，以及催化链延长的蛋氨酸同源物转化的Arabidopsis thaliana酶CYP79F1和CYP79F2。在植物中转基因表达该DNA或其部分可以用于操纵相应的硫代葡萄糖苷或氰基葡萄糖苷的生物合成。
• PESTICIDAL COMPOSITION COMPRISING INDOLE DERIVATES
  申请人：Bednarek Pawel

  公开号：US20090028796A1

  公开（公告）日：2009-01-29

  The present invention is directed to pesticidal compositions comprising indole derivatives. These indole derivatives are especially active against phytopathogenic fungi. Furthermore, the invention relates to the use of indole derivatives for the production of pesticides and the use of the compositions according to the invention as pesticides. The present invention is also directed to a process for producing a pesticidal composition and to pesticidal compositions prepared by this process. In addition, the invention relates to a process for preventing or combating pests and to a process for protecting plants against pests, especially against phytopathogenic fungi. Further, the invention is directed to plants or seeds as well as objects or materials which have been protected against pests by treatment with a composition according to the invention. Further, the invention is directed to a method for identifying a substance having pesticidal activity. Further, the invention is directed to a method of identifying the mode of action of and/or of providing binding proteins for a pesticidal compound of the present invention. Finally, the invention is directed to a method for diagnosing pest infection of a plant and to the use of a pesticidal compound of the present invention as diagnostic markers.

  本发明涉及包含吲哚衍生物的杀虫组合物。这些吲哚衍生物特别对植物病原真菌具有活性。此外，本发明涉及使用吲哚衍生物制备杀虫剂以及使用本发明中的组合物作为杀虫剂。本发明还涉及制备杀虫组合物的过程以及通过该过程制备的杀虫组合物。此外，本发明还涉及预防或对抗害虫的过程以及保护植物免受害虫，特别是植物病原真菌的过程。此外，本发明还涉及经过本发明中的组合物处理后受到保护的植物或种子以及物体或材料。本发明还涉及识别具有杀虫活性的物质的方法。此外，本发明还涉及识别本发明中杀虫化合物的作用方式和/或提供结合蛋白的方法。最后，本发明涉及诊断植物害虫感染的方法以及使用本发明中的杀虫化合物作为诊断标记的方法。
• Cytosolic γ-Glutamyl Peptidases Process Glutathione Conjugates in the Biosynthesis of Glucosinolates and Camalexin in <i>Arabidopsis</i>    
  作者：Fernando Geu-Flores、Morten Emil Møldrup、Christoph Böttcher、Carl Erik Olsen、Dierk Scheel、Barbara Ann Halkier

  DOI：10.1105/tpc.111.083998

  日期：2011.6.1

  The defense-related plant metabolites known as glucosinolates play important roles in agriculture, ecology, and human health. Despite an advanced biochemical understanding of the glucosinolate pathway, the source of the reduced sulfur atom in the core glucosinolate structure remains unknown. Recent evidence has pointed toward GSH, which would require further involvement of a GSH conjugate processing enzyme. In this article, we show that an Arabidopsis thaliana mutant impaired in the production of the γ-glutamyl peptidases GGP1 and GGP3 has altered glucosinolate levels and accumulates up to 10 related GSH conjugates. We also show that the double mutant is impaired in the production of camalexin and accumulates high amounts of the camalexin intermediate GS-IAN upon induction. In addition, we demonstrate that the cellular and subcellular localization of GGP1 and GGP3 matches that of known glucosinolate and camalexin enzymes. Finally, we show that the purified recombinant GGPs can metabolize at least nine of the 10 glucosinolate-related GSH conjugates as well as GS-IAN. Our results demonstrate that GSH is the sulfur donor in the biosynthesis of glucosinolates and establish an in vivo function for the only known cytosolic plant γ-glutamyl peptidases, namely, the processing of GSH conjugates in the glucosinolate and camalexin pathways.

  被称为葡萄糖硫醇苷的防御相关植物代谢物在农业、生态和人类健康中都扮演着重要角色。尽管对葡萄糖硫醇苷途径的生物化学理解已经很先进，但核心葡萄糖硫醇苷结构中还原硫原子的来源仍然未知。最近的证据指出了GSH，这将需要进一步涉及GSH结合物处理酶。在本文中，我们展示了一种Arabidopsis thaliana突变体，其生产γ-谷氨酰肽酶GGP1和GGP3受损，其葡萄糖硫醇苷水平发生改变，并积累了多达10个相关的GSH结合物。我们还展示了双突变体在产生卡马雷辛方面存在障碍，并在诱导后积累高量的卡马雷辛中间体GS-IAN。此外，我们证明了GGP1和GGP3的细胞和亚细胞定位与已知的葡萄糖硫醇苷和卡马雷辛酶相匹配。最后，我们展示了纯化的重组GGP能够代谢至少10个与葡萄糖硫醇苷相关的GSH结合物以及GS-IAN。我们的结果表明，GSH是葡萄糖硫醇苷生物合成中的硫供体，并为唯一已知的细胞质植物γ-谷氨酰肽酶建立了在体功能，即处理葡萄糖硫醇苷和卡马雷辛途径中的GSH结合物。