4-hydroxyphenylacetaldoxime | 70365-12-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-hydroxyphenylacetaldoxime
• 英文别名: Z-p-hydroxyphenylacetaldoxime；4-Hydroxy-phenylacetaldehyd-syn-oxim；(Z)-(4-hydroxyphenyl)acetaldehyde oxime；4-[(2Z)-2-hydroxyiminoethyl]phenol
• CAS: 70365-12-7
• 化学式: C₈H₉NO₂
• 分子量: 151.165
• InChiKey: TVXJJNJGTDWFLD-TWGQIWQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  52.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxyphenylacetaldoxime 生成 对羟基苯乙腈 、 水
  参考文献：
  名称：

  Dhurrin Synthesis in Sorghum Is Regulated at the Transcriptional Level and Induced by Nitrogen Fertilization in Older Plants

  摘要：

  高粱（Sorghum bicolor L. Moench）中的氰糖苷dhurrin的含量取决于植物的年龄和生长条件。在发芽后不久，氰化物潜力最高。在这个阶段，氮肥的施用对dhurrin含量没有影响，而在较老的植物中，氮肥的施用会引起增加。在所有阶段，dhurrin的含量与两种生物合成酶CYP79A1和CYP71E1的活性以及这两种酶的蛋白质和mRNA水平密切相关。在发育过程中，CYP79A1的活性低于CYP71E1的活性，这表明CYP79A1催化dhurrin合成的速率限制步骤，这与使用暗化的幼苗已经显示的结果一致。dhurrin合成的位置在植物发育过程中从叶子转移到茎。综合结果表明，高粱中的dhurrin含量主要由生物合成酶CYP79A1和CYP71E1的转录调控决定。

  DOI：

  10.1104/pp.000687
• 作为产物：
  描述：

  4-羟基苯乙酸甲酯 在 盐酸羟胺 、 sodium acetate 、 二异丁基氢化铝 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 11.0h， 生成 4-hydroxyphenylacetaldoxime
  参考文献：
  名称：

  探索十字花科植物的真菌病原体中关键的代谢途径：吲哚-3-乙醛肟，4-羟苯基乙醛肟及其代谢物的生物转化。

  摘要：

  吲哚-3-乙醛肟是十字花科植物不同植物次生代谢产物生物合成中至关重要的中间体。在十字花科植物中引起重要植物病的真菌，吲哚-3-乙醛肟经吲哚-3-乙腈代谢为吲哚-3-乙酸，黄斑病的致病性黑斑病致病因子，黑腿病的致病因子，茄根枯菌的致病因子描述了根腐病和干腐病的核盘菌菌核病病原体。同样，还报道了吲哚-3-乙醛肟和代谢物的抗真菌活性以及相同植物病原体和昆虫真菌病原体球孢白僵菌对4-羟基苯基乙醛肟的合成和生物转化。

  DOI：

  10.1016/s0968-0896(03)00241-4

文献信息

• Cytochrome P450 monooxygenases
  申请人：——

  公开号：US20030041346A1

  公开（公告）日：2003-02-27

  Cytochrome P450 II dependent monooxygenases and DNA molecules encoding these monooxygenases are provided, which are able to catalyze the biosynthethic conversion of aldoximes to nitrils and the conversion of said nitrils to the corresponding cyanohydrins, which are the presursors of cyanogenic glycosides. Moreover, the invention provides methods for obtaining DNA molecules according to the invention and methods for obtaining transgenic plants resistant to insects, acarids, or nematodes or plants with improved nutritive value.

  本发明提供了依赖于细胞色素P450II的单加氧酶和编码这些单加氧酶的DNA分子，这些单加氧酶能够催化醛肟的生物合成转化为腈和将所述腈转化为相应的氰醇，这些是青霉素糖苷的前体。此外，本发明还提供了根据本发明获得DNA分子的方法和获得对昆虫、螨虫或线虫具有抗性或具有改善营养价值的转基因植物的方法。
• 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。
• Metabolic engineering of dhurrin in transgenic <i>Arabidopsis</i> plants with marginal inadvertent effects on the metabolome and transcriptome
  作者：Charlotte Kristensen、Marc Morant、Carl Erik Olsen、Claus T. Ekstrøm、David W. Galbraith、Birger Lindberg Møller、Søren Bak

  DOI：10.1073/pnas.0409233102

  日期：2005.2

  Focused and nontargeted approaches were used to assess the impact associated with introduction of new high-flux pathways in Arabidopsis thaliana by genetic engineering. Transgenic A. thaliana plants expressing the entire biosynthetic pathway for the tyrosine-derived cyanogenic glucoside dhurrin as accomplished by insertion of CYP79A1 , CYP71E1 , and UGT85B1 from Sorghum bicolor were shown to accumulate 4% dry-weight dhurrin with marginal inadvertent effects on plant morphology, free amino acid pools, transcriptome, and metabolome. In a similar manner, plants expressing only CYP79A1 accumulated 3% dry weight of the tyrosine-derived glucosinolate, p -hydroxybenzylglucosinolate with no morphological pleitropic effects. In contrast, insertion of CYP79A1 plus CYP71E1 resulted in stunted plants, transcriptome alterations, accumulation of numerous glucosides derived from detoxification of intermediates in the dhurrin pathway, and in loss of the brassicaceae-specific UV protectants sinapoyl glucose and sinapoyl malate and kaempferol glucosides. The accumulation of glucosides in the plants expressing CYP79A1 and CYP71E1 was not accompanied by induction of glycosyltransferases, demonstrating that plants are constantly prepared to detoxify xenobiotics. The pleiotrophic effects observed in plants expressing sorghum CYP79A1 and CYP71E1 were complemented by retransformation with S. bicolor UGT85B . These results demonstrate that insertion of high-flux pathways directing synthesis and intracellular storage of high amounts of a cyanogenic glucoside or a glucosinolate is achievable in transgenic A. thaliana plants with marginal inadvertent effects on the transcriptome and metabolome.

  采用有针对性和非有针对性的方法，评估了通过基因工程引入新的高通量途径对拟南芥的影响。表达了源自高粱的整个酪氨酸衍生的氰甙dhurrin的生物合成途径，包括插入了CYP79A1、CYP71E1和UGT85B1，的转基因拟南芥植物被证明可以积累4%的dhurrin干重，对植物形态、游离氨基酸池、转录组和代谢组的不良影响微乎其微。同样，只表达CYP79A1的植物可以积累3%的酪氨酸衍生的糖苷，即p-羟基苯甲醇糖苷，没有形态多向性影响。相比之下，插入CYP79A1和CYP71E1会导致矮化的植物、转录组改变、积累许多源自dhurrin途径中间产物解毒的糖苷，以及失去十字花科特有的紫外线保护剂芥子酰葡萄糖和芥子酰苹果酸和卡培菲糖苷。表达CYP79A1和CYP71E1的植物中糖苷的积累并未伴随着糖基转移酶的诱导，表明植物始终准备解毒外源物质。通过重新转化S.bicolor UGT85B，可以补充表达高粱CYP79A1和CYP71E1的植物中观察到的多向性效应。这些结果表明，在转基因拟南芥植物中插入定向合成和细胞内储存大量氰甙或糖苷的高通量途径是可行的，对转录组和代谢组的不良影响微乎其微。
• Udp-glucose aglycon-glucosytransferase
  申请人：Möller Linberg Birger

  公开号：US20050277766A1

  公开（公告）日：2005-12-15

  The present invention provides DNA molecules coding for UDP-glucose:aglycon-glucosyltransferase conjugating cyanohydrins, terpenoids, phenylderivatives or hexanolderivatives to glucose. Transgenic expression of corresponding genes in plants can be used to influence the biosynthesis of the corresponding glucosides.

  本发明提供了编码 UDP-葡萄糖：苷元-葡萄糖基转移酶的 DNA 分子，可将氰醇、萜类化合物、苯基衍生物或己基衍生物与葡萄糖连接。植物中相应基因的转基因表达可用于影响相应葡萄糖苷的生物合成。
• The bifurcation of the cyanogenic glucoside and glucosinolate biosynthetic pathways
  作者：Mette Clausen、Rubini M. Kannangara、Carl E. Olsen、Cecilia K. Blomstedt、Roslyn M. Gleadow、Kirsten Jørgensen、Søren Bak、Mohammed S. Motawie、Birger Lindberg Møller

  DOI：10.1111/tpj.13023

  日期：2015.11

  SummaryThe biosynthetic pathway for the cyanogenic glucoside dhurrin in sorghum has previously been shown to involve the sequential production of (E)‐ and (Z)‐p‐hydroxyphenylacetaldoxime. In this study we used microsomes prepared from wild‐type and mutant sorghum or transiently transformed Nicotiana benthamiana to demonstrate that CYP79A1 catalyzes conversion of tyrosine to (E)‐p‐hydroxyphenylacetaldoxime whereas CYP71E1 catalyzes conversion of (E)‐p‐hydroxyphenylacetaldoxime into the corresponding geometrical Z‐isomer as required for its dehydration into a nitrile, the next intermediate in cyanogenic glucoside synthesis. Glucosinolate biosynthesis is also initiated by the action of a CYP79 family enzyme, but the next enzyme involved belongs to the CYP83 family. We demonstrate that CYP83B1 from Arabidopsis thaliana cannot convert the (E)‐p‐hydroxyphenylacetaldoxime to the (Z)‐isomer, which blocks the route towards cyanogenic glucoside synthesis. Instead CYP83B1 catalyzes the conversion of the (E)‐p‐hydroxyphenylacetaldoxime into an S‐alkyl‐thiohydroximate with retention of the configuration of the E‐oxime intermediate in the final glucosinolate core structure. Numerous microbial plant pathogens are able to detoxify Z‐oximes but not E‐oximes. The CYP79‐derived E‐oximes may play an important role in plant defense.