2,4,6-trichlorophenolate | 51247-74-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,4,6-trichlorophenolate
• CAS: 51247-74-6
• 化学式: C₆H₂Cl₃O
• 分子量: 196.44
• InChiKey: LINPIYWFGCPVIE-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,4,6-trichlorophenolate 在 氧气 作用下， 生成 2,4,6-trichlorophenoxyl radical
  参考文献：
  名称：

  Autoxidation of closed-shell organics: an outer-sphere electron transfer

  摘要：

  DOI：

  10.1021/ja00064a088
• 作为产物：
  描述：

  2,4,6-三氯苯酚 在 corresponding R₄NOH 作用下， 以 甲醇 为溶剂， 生成 2,4,6-trichlorophenolate
  参考文献：
  名称：

  氢-双酚盐配合物在丙酮中的氢键和质子转移

  摘要：

  的同共轭，（ARO）2 ħ - ，和heteroconjugation，Ar'O - ⋯HOAR，（其中Ar是芳族的）与质子转移已经在丙酮在298K四烷基酚确定与各种酚类到滴定给定同质复合体和异质复合体。电位数据提供了总体平衡常数K 0，质子转移常数K PT和形成常数K f。研究了两种类型的杂合物。当ArO –是弱于Ar'O –的碱时，络合发生而没有质子转移，这由低K 0所证实。反应的值。当ArO –是比Ar'O –更强的碱时，整体平衡常数K 0很大，因为氢键的平衡质子转移常数（K PT）和平衡形成常数（K f）都包括在其中。K 0 = K f K PT的测量。

  DOI：

  10.1039/f19827802157

文献信息

• Cork Taint of Wines: Role of the Filamentous Fungi Isolated from Cork in the Formation of 2,4,6-Trichloroanisole by O Methylation of 2,4,6-Trichlorophenol
  作者：María Luisa Álvarez-Rodríguez、Laura López-Ocaña、José Miguel López-Coronado、Enrique Rodríguez、María Jesús Martínez、Germán Larriba、Juan-José R. Coque

  DOI：10.1128/aem.68.12.5860-5869.2002

  日期：2002.12

  Cork taint is a musty or moldy off-odor in wine mainly caused by 2,4,6-trichloroanisole (2,4,6-TCA). We examined the role of 14 fungal strains isolated from cork samples in the production of 2,4,6-TCA by O methylation of 2,4,6-trichlorophenol (2,4,6-TCP). The fungal strains isolated belong to the genera Penicillium (four isolates); Trichoderma (two isolates); and Acremonium, Chrysonilia, Cladosporium

  软木塞味是葡萄酒中发霉或发霉的异味，主要由2,4,6-三氯茴香醚（2,4,6-TCA）引起。我们检查了从软木样品中分离出的14种真菌菌株在通过2,4,6-三氯苯酚（2,4,6-TCP）的O甲基化生产2,4,6-TCA中的作用。分离出的真菌菌株属于青霉属（4个分离株）。木霉（两个分离株）；以及顶头孢属，Ch属，枝孢菌属，镰刀菌属，线虫，Mucor，拟青霉菌和黄萎病菌（各一种）。当它们在2,4,6-TCP存在下直接在软木上生长时，其中11个菌株可以产生2,4,6-TCA。木霉和镰刀菌菌株进行了最高水平的生物转化。一株长木霉菌还可以在液体培养基中有效产生2,4,6-TCA。但是，没有可检测到的2,4水平，当测试除2,4,6-TCP以外的推定前体（包括几种茴香，二氯苯酚，三氯苯酚或其他高度氯化的化合物）时，可以在软木塞上检测到此菌株产生的6-TCA。液体培养的时程表达研究表明，高浓度的葡萄糖（2％或111
• Characterization of an Inducible Chlorophenol <i>O</i> -Methyltransferase from <i>Trichoderma longibrachiatum</i> Involved in the Formation of Chloroanisoles and Determination of Its Role in Cork Taint of Wines
  作者：Juan-José R. Coque、María Luisa Álvarez-Rodríguez、Germán Larriba

  DOI：10.1128/aem.69.9.5089-5095.2003

  日期：2003.9

  A novel S -adenosyl- l -methionine (SAM)-dependent methyltransferase catalyzing the O methylation of several chlorophenols and other halogenated phenols was purified 220-fold to apparent homogeneity from mycelia of Trichoderma longibrachiatum CECT 20431. The enzyme could be identified in partially purified protein preparations by direct photolabeling with [ methyl - ³ H]SAM, and this reaction was prevented by previous incubation with S -adenosylhomocysteine. Gel filtration indicated that the M _r was 112,000, and sodium dodecyl sulfate-polyacrylamide gel electrophoresis showed that the enzyme was composed of two subunits with molecular weights of approximately 52,500. The enzyme had a pH optimum between 8.2 and 8.5 and an optimum temperature of 28°C, with a pI of 4.9. The K _m values for 2,4,6-trichlorophenol and SAM were 135.9 ± 12.8 and 284.1 ± 35.1 μM, respectively. S -Adenosylhomocysteine acted as a competitive inhibitor, with a K _i of 378.9 ± 45.4 μM. The methyltransferase was also strongly inhibited by low concentrations of several metal ions, such as Cu ²⁺ , Hg ²⁺ , Zn ²⁺ , and Ag ⁺ , and to a lesser extent by p -chloromercuribenzoic acid, but it was not significantly affected by several thiols or other thiol reagents. The methyltransferase was specifically induced by several chlorophenols, especially if they contained three or more chlorine atoms in their structures. Substrate specificity studies showed that the activity was also specific for halogenated phenols containing fluoro, chloro, or bromo substituents, whereas other hydroxylated compounds, such as hydroxylated benzoic acids, hydroxybenzaldehydes, phenol, 2-metoxyphenol, and dihydroxybenzene, were not methylated.

  摘要 新颖的 S -腺苷 l 一种新型 S-腺苷-l-蛋氨酸（SAM）依赖性甲基转移酶催化了几种氯苯酚和其他卤代苯酚的 O 型甲基化。 菌丝体中纯化了 220 倍，达到明显的同质性。 CECT 20431。在部分纯化的蛋白质制备物中，可以用[......]直接光标记来鉴定这种酶。 甲基 - 3 H]SAM直接光标记，这种反应可通过事先与 S 腺苷-高半胱氨酸孵育可阻止这种反应。凝胶过滤表明 M r 十二烷基硫酸钠-聚丙烯酰胺凝胶电泳显示，该酶由分子量约为 52,500 的两个亚基组成。该酶的最适 pH 值为 8.2 至 8.5，最适温度为 28°C，pI 为 4.9。其pI为4.9。 K m 分别为 135.9 ± 12.8 和 284.1 ± 35.1 μM。 S -腺苷高半胱氨酸是一种竞争性抑制剂，其 K K i 为 378.9 ± 45.4 μM。甲基转移酶还受到几种低浓度金属离子的强烈抑制，如 Cu 2+ 、Hg 2+ 、Zn 2+ 和 Ag + ，其次是 p -氯巯基苯甲酸，但它受几种硫醇或其他硫醇试剂的影响不大。甲基转移酶受到几种氯酚的特异性诱导，尤其是当它们的结构中含有三个或三个以上的氯原子时。底物特异性研究表明，该活性对含有氟、氯或溴取代基的卤代苯酚也有特异性，而其他羟基化合物，如羟基苯甲酸、羟基苯甲醛、苯酚、2-甲氧基苯酚和二羟基苯则不能被甲基化。
• Genetic and Biochemical Characterization of a 2,4,6-Trichlorophenol Degradation Pathway in <i>Ralstonia eutropha</i> JMP134
  作者：Tai Man Louie、Christopher M. Webster、Luying Xun

  DOI：10.1128/jb.184.13.3492-3500.2002

  日期：2002.7

  Ralstonia eutropha JMP134 can grow on several chlorinated aromatic pollutants, including 2,4-dichlorophenoxyacetate and 2,4,6-trichlorophenol (2,4,6-TCP). Although a 2,4,6-TCP degradation pathway in JMP134 has been proposed, the enzymes and genes responsible for 2,4,6-TCP degradation have not been characterized. In this study, we found that 2,4,6-TCP degradation by JMP134 was inducible by 2,4,6-TCP and subject to catabolic repression by glutamate. We detected 2,4,6-TCP-degrading activities in JMP134 cell extracts. Our partial purification and initial characterization of the enzyme indicated that a reduced flavin adenine dinucleotide (FADH ₂ )-utilizing monooxygenase converted 2,4,6-TCP to 6-chlorohydroxyquinol (6-CHQ). The finding directed us to PCR amplify a 3.2-kb fragment containing a gene cluster ( tcpABC ) from JMP134 by using primers designed from conserved regions of FADH ₂ -utilizing monooxygenases and hydroxyquinol 1,2-dioxygenases. Sequence analysis indicated that tcpA , tcpB , and tcpC encoded an FADH ₂ -utilizing monooxygenase, a probable flavin reductase, and a 6-CHQ 1,2-dioxygenase, respectively. The three genes were individually inactivated in JMP134. The tcpA mutant failed to degrade 2,4,6-TCP, while both tcpB and tcpC mutants degraded 2,4,6-TCP to an oxidized product of 6-CHQ. Insertional inactivation of tcpB may have led to a polar effect on downstream tcpC , and this probably resulted in the accumulation of the oxidized form of 6-CHQ. For further characterization, TcpA was produced, purified, and shown to transform 2,4,6-TCP to 6-CHQ when FADH ₂ was supplied by an Escherichia coli flavin reductase. TcpC produced in E. coli oxidized 6-CHQ to 2-chloromaleylacetate. Thus, our data suggest that JMP134 transforms 2,4,6-TCP to 2-chloromaleylacetate by TcpA and TcpC. Sequence analysis suggests that tcpB may function as an FAD reductase, but experimental data did not support this hypothesis. The function of TcpB remains unknown.

  摘要 Ralstonia eutropha JMP134 可在几种氯化芳烃污染物上生长，包括 2,4 二氯苯氧乙酸酯和 2,4,6- 三氯苯酚（2,4,6-TCP）。虽然有人提出了 JMP134 中 2,4,6-TCP 的降解途径，但负责 2,4,6-TCP 降解的酶和基因尚未定性。本研究发现，2,4,6-TCP 可诱导 JMP134 降解 2,4,6-TCP，谷氨酸可抑制 2,4,6-TCP的分解。我们在 JMP134 细胞提取物中检测到了 2,4,6-TCP 降解活性。我们对该酶进行了部分纯化和初步鉴定，结果表明，还原型黄素腺嘌呤二核苷酸（FADH 2 )利用单加氧酶将 2,4,6-三氯丙醇转化为 6-氯羟基喹啉（6-CHQ）。这一发现指导我们 PCR 扩增了一个 3.2-kb 的片段，其中包含一个基因簇（TCPABC）。 TCPABC )的 3.2-kb 片段。 2 利用单加氧酶和羟基醌 1,2-二加氧酶的保守区域设计的引物，从 JMP134 中扩增出含有基因簇 ( TCPABC ) 的 3.2-kb 片段。序列分析表明 TCPA , TCPB 和 TCPa href=https://www.molaid.com/MS_17084 target="_blank">PC 编码了 FADH 2 -利用的单加氧酶、可能的黄素还原酶和 6-CHQ 1,2 二加氧酶。这三个基因在 JMP134 中分别失活。在 TCPA 突变体不能降解 2,4,6-三氯丙醇，而 TCPB 和 TCPa href=https://www.molaid.com/MS_17084 target="_blank">PC 突变体则将 2,4,6-TCP 降解为 6-CHQ 的氧化产物。插入失活的 TCPB 可能对下游的 TCPa href=https://www.molaid.com/MS_17084 target="_blank">PC 的极性效应，这可能导致了 6-CHQ 氧化形式的积累。为了进一步确定其特性，生产并纯化了 TCPA，结果表明当 FADH 2 时，TCPA 能将 2,4,6-三氯丙醇转化为 6-CHQ 大肠杆菌 黄素还原酶提供 FADH 2 时，将 2,4,6-TCP 转化为 6-CHQ。在 大肠杆菌 将 6-CHQ 氧化为 2-氯马来酰乙酸酯。因此，我们的数据表明，JMP134 通过 TCPA 和 TCPa href=https://www.molaid.com/MS_17084 target="_blank">PC 将 2,4,6-三氯丙醇转化为 2-氯马来酰乙酸酯。序列分析表明 TCPB 可能具有 FAD 还原酶的功能，但实验数据并不支持这一假设。TCPB 的功能仍然未知。
• Thermodynamics of proton transfer in phenol-acetate hydrogen bonds with large proton polarizability and the conversion of light energy into chemical energy in bacteriorhodopsin
  作者：Helmut Merz、Ulrike Tangermann、Georg Zundel

  DOI：10.1021/j100282a024

  日期：1986.11
• Characterization of a novel 2,4,6-trichlorophenol-inducible gene encoding chlorophenol O-methyltransferase from Trichoderma longibrachiatum responsible for the formation of chloroanisoles and detoxification of chlorophenols
  作者：Raúl Feltrer、María Luisa Álvarez-Rodríguez、Carlos Barreiro、Ramiro P. Godio、Juan-José R. Coque

  DOI：10.1016/j.fgb.2010.02.002

  日期：2010.5

  De novo sequencing of eight internal peptides of purified chlorophenol O-methyltransferase, or CMT1 (before named as CPOMT), from Trichoderma longibrachiatum was performed by MALDI-TOF/TOF and ESI-IT. A novel gene (cmt1) encoding CMT1 was cloned by using a PCR approach based on the amino acid sequence of two internal peptides. The gene (1637 bp) encoded a protein of 468 amino acids with a deduced molecular mass of 52.4 kDa, and a theoretical isoelectric point of 5.93. This gene contains four introns, whose location was confirmed by comparison of cDNA and chromosomal sequences. The expression of cmt1 gene was induced at transcriptional level by exposure of fungal mycelia to 2,4,6-trichlorophenol (2,4,6-TCP). Putative homologous genes were detected in many different fungal strains, including other Trichoderma species. Partial silencing of cmt1 gene resulted in a 48.9% (+/- 5.2) decrease of CMT1 activity levels in a T. longibrachiatum At37 transformant strain by comparison with the wild type, whereas a decrease of up to 53.0% was observed in the levels of 2,4,6-TCA produced in liquid cultures. Efficient expression of cmt1 gene in Escherichia coli unequivocally confirmed that it encodes a CMT1 enzyme. (C) 2010 Elsevier Inc. All rights reserved.