2,3,5-Trichloro-cis,cis-muconate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2,3,5-Trichloro-cis,cis-muconate
• 英文别名: (2Z,4E)-2,3,5-trichlorohexa-2,4-dienedioate
• 化学式: C6HCl3O4-2
• 分子量: 243.4
• InChiKey: AHDWVTPNJCBFTN-TZFCGSKZSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,3,5-Trichloro-6-hydroxyphenolate 、 氧气 生成 2,3,5-Trichloro-cis,cis-muconate 、 氢(+1)阳离子
  参考文献：
  名称：

  Sequence analysis of the Pseudomonas sp. strain P51 tcb gene cluster, which encodes metabolism of chlorinated catechols: evidence for specialization of catechol 1,2-dioxygenases for chlorinated substrates

  摘要：

  Pseudomonas sp.菌株P51含有位于降解质粒pP51上的两个基因簇，编码对氯代苯降解。确定了一个5,499 bp区域的核苷酸序列，其中包含氯间苯二酚氧化基因簇tcbCDEF。序列包含五个大的开放阅读框架，它们都是共线的。用各种大肠杆菌表达系统和酶活性分析研究了这些开放阅读框架的功能。第一个基因tcbC编码一个27.5 kDa的蛋白质，具有氯间苯二酚1,2-双加氧酶活性。tcbC基因后面是tcbD，它编码环异构酶II（39.5 kDa）；一个具有未知功能的大开放阅读框架（ORF3）；tcbE，它编码水解酶II（25.8 kDa）；以及tcbF，它编码一个假定的反式二烯酸内酯酶（37.5 kDa）。tcbCDEF基因簇显示出强的DNA同源性（57.6%至72.1%的同一性）和与其他已知质粒编码的氯间苯二酚代谢操作子的组织类似性，例如Pseudomonas putida的clcABD和Alcaligenes eutrophus JMP134的tfdCDEF。三个操作子中功能相关酶的氨基酸序列之间的同一性在50.6%至75.7%之间变化，其中tcbCDEF和tfdCDEF对的相似性最小。测量由tcbC、clcA和tfdC编码的氯间苯二酚1,2-双加氧酶的特异性活性表明，类型II酶之间存在专业化。TcbC优先转化3,4-二氯间苯二酚相对于其他氯化间苯二酚，而TfdC对3,5-二氯间苯二酚的活性更高。ClcA处于中间位置，对3-氯间苯二酚具有最高的活性水平，对3,5-二氯间苯二酚具有次高的水平。

  DOI：

  10.1128/jb.173.8.2425-2434.1991

文献信息

• Sequence analysis of the Pseudomonas sp. strain P51 tcb gene cluster, which encodes metabolism of chlorinated catechols: evidence for specialization of catechol 1,2-dioxygenases for chlorinated substrates
  作者：J R van der Meer、R I Eggen、A J Zehnder、W M de Vos

  DOI：10.1128/jb.173.8.2425-2434.1991

  日期：1991.4

  Pseudomonas sp. strain P51 contains two gene clusters located on catabolic plasmid pP51 that encode the degradation of chlorinated benzenes. The nucleotide sequence of a 5,499-bp region containing the chlorocatechol-oxidative gene cluster tcbCDEF was determined. The sequence contained five large open reading frames, which were all colinear. The functionality of these open reading frames was studied with various Escherichia coli expression systems and by analysis of enzyme activities. The first gene, tcbC, encodes a 27.5-kDa protein with chlorocatechol 1,2-dioxygenase activity. The tcbC gene is followed by tcbD, which encodes cycloisomerase II (39.5 kDa); a large open reading frame (ORF3) with an unknown function; tcbE, which encodes hydrolase II (25.8 kDa); and tcbF, which encodes a putative trans-dienelactone isomerase (37.5 kDa). The tcbCDEF gene cluster showed strong DNA homology (between 57.6 and 72.1% identity) and an organization similar to that of other known plasmid-encoded operons for chlorocatechol metabolism, e.g., clcABD of Pseudomonas putida and tfdCDEF of Alcaligenes eutrophus JMP134. The identity between amino acid sequences of functionally related enzymes of the three operons varied between 50.6 and 75.7%, with the tcbCDEF and tfdCDEF pair being the least similar of the three. Measurements of the specific activities of chlorocatechol 1,2-dioxygenases encoded by tcbC, clcA, and tfdC suggested that a specialization among type II enzymes has taken place. TcbC preferentially converts 3,4-dichlorocatechol relative to other chlorinated catechols, whereas TfdC has a higher activity toward 3,5-dichlorocatechol. ClcA takes an intermediate position, with the highest activity level for 3-chlorocatechol and the second-highest level for 3,5-dichlorocatechol.

  Pseudomonas sp.菌株P51含有位于降解质粒pP51上的两个基因簇，编码对氯代苯降解。确定了一个5,499 bp区域的核苷酸序列，其中包含氯间苯二酚氧化基因簇tcbCDEF。序列包含五个大的开放阅读框架，它们都是共线的。用各种大肠杆菌表达系统和酶活性分析研究了这些开放阅读框架的功能。第一个基因tcbC编码一个27.5 kDa的蛋白质，具有氯间苯二酚1,2-双加氧酶活性。tcbC基因后面是tcbD，它编码环异构酶II（39.5 kDa）；一个具有未知功能的大开放阅读框架（ORF3）；tcbE，它编码水解酶II（25.8 kDa）；以及tcbF，它编码一个假定的反式二烯酸内酯酶（37.5 kDa）。tcbCDEF基因簇显示出强的DNA同源性（57.6%至72.1%的同一性）和与其他已知质粒编码的氯间苯二酚代谢操作子的组织类似性，例如Pseudomonas putida的clcABD和Alcaligenes eutrophus JMP134的tfdCDEF。三个操作子中功能相关酶的氨基酸序列之间的同一性在50.6%至75.7%之间变化，其中tcbCDEF和tfdCDEF对的相似性最小。测量由tcbC、clcA和tfdC编码的氯间苯二酚1,2-双加氧酶的特异性活性表明，类型II酶之间存在专业化。TcbC优先转化3,4-二氯间苯二酚相对于其他氯化间苯二酚，而TfdC对3,5-二氯间苯二酚的活性更高。ClcA处于中间位置，对3-氯间苯二酚具有最高的活性水平，对3,5-二氯间苯二酚具有次高的水平。