Zn-coproporphyrin III | 134052-33-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: Zn-coproporphyrin III
• CAS: 134052-33-8
• 化学式: C₃₆H₃₆N₄O₈Zn
• 分子量: 718.094
• InChiKey: PTIRZWHASNDUGZ-RGGAHWMASA-L

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  甲醇 、 Zn-coproporphyrin III 在 盐酸 作用下， 以 水 为溶剂， 反应 2.0h， 以0.3 mg的产率得到
  参考文献：
  名称：

  A Unique Combination of Two Different Quorum Sensing Systems in the β-Rhizobium Cupriavidus taiwanensis

  摘要：

  Cupriavidus taiwanensis LMG19424, a beta-rhizobial symbiont of Mimosa pudica, harbors phc and tqs quorum sensing (QS), which are the homologous cell-cell communication systems previously identified from the plant pathogen Ralstonia solanacearum and the human pathogen Vibrio cholerae, respectively. However, there has been no experimental evidence reported that these QS systems function in C. taiwanensis LMG19424. We identified (R)-methyl 3-hydroxymyristate (3-OH MAME) and (S)-3-hydroxypentadecan-4-one (C-15-AHK) as phc and tqs QS signals, respectively, and characterized these QS systems. The expression of the signal synthase gene phcB and tqsA in E. coli BL21(DE3) resulted in the high production of 3-OH MAME and C-15-AHK, respectively. Their structures were elucidated by comparison of EI-MS data and GC/chiral LC retention times with synthetic standards. The deletion of phcB reduced cell motility and increased biofilm formation, and the double deletion of phcB/tqsA caused the accumulation of the metal chelator coproporphyrin III in its mutant culture. Although the deletion of phcB and tqsA slightly reduced its ability to nodulate on aseptically grown seedlings of M. pudica, there was no significant difference in nodule formation between LMG19424 and its QS mutants when commercial soils were used. Taken together, this is the first example of the simultaneous production of 3-OH MAME/C-15-AHK as QS signals in a bacterial species, and the importance of the phc/tqs QS systems in the saprophytic stage of C. taiwanensis LMG19424 is suggested.

  DOI：

  10.1021/acs.jnatprod.0c00054
• 作为产物：
  描述：

  coproporphyrin III dihydrochloride 、 zinc diacetate 以 水 、 二甲基亚砜 为溶剂， 以68.3%的产率得到Zn-coproporphyrin III
  参考文献：
  名称：

  Growth Mechanism of Uncultured Actinobacterial Strain Leucobacter sp. ASN212 by Zinc Coproporphyrin

  摘要：

  We propose HemH as a primary target of Zn coproporphyrin, which stimulates the growth of uncultured Leucobacter sp. ASN212, based on the structure-activity relationship for transition-metal complexes of coproporphyrin.

  DOI：

  10.3987/com-16-s(s)31

文献信息

• The auxiliary [4Fe–4S] cluster of the Radical SAM heme synthase from Methanosarcina barkeri is involved in electron transfer
  作者：Melanie Kühner、Peter Schweyen、Martin Hoffmann、José Vazquez Ramos、Edward J. Reijerse、Wolfgang Lubitz、Martin Bröring、Gunhild Layer

  DOI：10.1039/c6sc01140c

  日期：——

  Radical SAM enzymes and contains two [4Fe–4S] clusters. Whereas one of these clusters is required for substrate radical formation, the role of the second iron–sulfur cluster is not known. In this study, the function of the auxiliary cluster during AhbD catalysis was investigated. Two single cluster variants of AhbD from M. barkeri carrying either one of the two clusters were created. Using these enzyme

  血红素合酶AhbD在还原硫酸盐的细菌和古细菌中发生的替代性血红素生物合成途径中，催化铁-卟啉铁III的两个丙酸酯侧链氧化脱羧成相应的血红素乙烯基。AhbD属于自由基SAM酶家族，包含两个[4Fe–4S]簇。尽管这些团簇之一是形成底物自由基的必要条件，但第二个铁硫团簇的作用尚不清楚。在这项研究中，研究了辅助簇在AhbD催化过程中的功能。从AhbD的两个单簇变体M.巴克创建了携带两个集群之一的集群。使用这些酶变体表明，底物结合和底物自由基的形成不需要辅助簇。相反，辅助簇参与AhbD催化的后期步骤，最有可能是电子从反应中间体转移到最终电子受体。此外，通过使用替代性底物（如卟啉Ⅲ，铜卟啉Ⅲ和锌卟啉Ⅲ）进行AhbD活性测定，可以观察到卟啉底物的中心铁离子也参与了电子从反应中间体到助剂的转移。 [4Fe–4S]群集。总之，获得了有关AhbD催化完全未表征的晚期步骤的新见解。