(4R,5S)-5-chloromuconolactone | 157762-78-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (4R,5S)-5-chloromuconolactone
• 英文别名: (2s)-2-Chloranyl-2-[(2r)-5-Oxidanylidene-2h-Furan-2-Yl]ethanoic Acid；(2S)-2-chloro-2-[(2R)-5-oxo-2H-furan-2-yl]acetic acid
• CAS: 157762-78-2
• 化学式: C₆H₅ClO₄
• 分子量: 176.556
• InChiKey: KGCZGOVWTWDEQD-WUJLRWPWSA-N

物化性质

• 沸点：
  452.1±20.0 °C(Predicted)
• 密度：
  1.588±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5S)-5-chloromuconolactone 在 chloromuconolactone dehalogenase from Rhodococcus opacus 1CP 作用下， 以 aq. phosphate buffer 为溶剂， 反应 1.5h， 生成 (2Z)-2-(5-氧代-2(5H)-呋喃亚基)-乙酸
  参考文献：
  名称：

  Recombinant expression of a unique chloromuconolactone dehalogenase ClcF from Rhodococcus opacus 1CP and identification of catalytically relevant residues by mutational analysis

  摘要：

  Chloromuconolactone dehalogenase ClcF plays a unique role in 3-chlorocatechol degradation by Rhodococcus opacus 1CP by compensating the inability of its chloromuconate cycloisomerase ClcB2 to dechlorinate the chemically stable cycloisomerization product (4R,5S)-5-chloromuconolactone (5CML). High sequence similarities showed relatedness of ClcF to muconolactone isomerases (MLIs, EC 5.3.3.4) of the 3-oxoadipate pathway. Although both enzyme types share the ability to dechlorinate 5CML, comparison of kcat/Km indicated a significant extent of specialization of ClcF for dechlorination. This assumption was substantiated by an almost complete inability of ClcF to convert (4S)-muconolactone and the exclusive formation of cis-dienelactone from 5CML. Mutational analysis of ClcF by means of variants E27D, E27Q, Y50A, N52A, and A89S indicated relevance of some highly conserved residues for substrate binding and catalysis. Based on the putative isomerization mechanism of MLI, evidence was provided for a role of E27 in initial proton abstraction as well as of Y50 and N52 in substrate binding. In case of N52 substrate binding is likely to occur to the carboxylic group of 5CML as indicated by a significant change of product specificity. Expression in Escherichia coli BL21-CP(DE)-RIL followed by a three-step purification procedure with heat treatment is a convenient strategy to obtain recombinant ClcF and variants thereof. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.abb.2012.07.007