marinophenazine B | 1478263-83-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: marinophenazine B
• 英文别名: Phenaziterpene A；6-[(2E)-3,7-dimethylocta-2,6-dienoxy]phenazin-1-ol
• CAS: 1478263-83-0
• 化学式: C₂₂H₂₄N₂O₂
• 分子量: 348.445
• InChiKey: GTZWCZPREISNMM-DTQAZKPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,6-二羟基吩嗪 、 香叶基焦磷酸铵盐 在 1,6-dihydroxyphenazine geranyltransferase from Streptomyces sp. CNQ-509 作用下， 以 aq. buffer 为溶剂， 反应 0.17h， 生成 marinophenazine B
  参考文献：
  名称：

  A Membrane-Bound Prenyltransferase Catalyzes the O-Prenylation of 1,6-Dihydroxyphenazine in the Marine BacteriumStreptomycessp. CNQ-509

  摘要：

  AbstractStreptomyces sp. CNQ‐509 produces the rare O‐prenylated phenazines marinophenazines A and B. To identify the enzyme catalyzing the O‐prenyl transfer in marinophenazine biosynthesis, we sequenced the genome of S. sp. CNQ‐509. This led to the identification of two genomic loci harboring putative phenazine biosynthesis genes. The first locus contains orthologues for all seven genes involved in phenazine‐1‐carboxylic acid biosynthesis in pseudomonads. The second locus contains two known phenazine biosynthesis genes and a putative prenyltransferase gene termed cnqPT1. cnqPT1 codes for a membrane protein with sequence similarity to the prenyltransferase UbiA of ubiquinone biosynthesis. The enzyme CnqPT1 was identified as a 1,6‐dihydroxyphenazine geranyltransferase, which catalyzes the CO bond formation between C‐1 of the geranyl moiety and O‐6 of the phenazine scaffold. CnqPT1 is the first example of a prenyltransferase catalyzing O‐prenyl transfer to a phenazine.

  DOI：

  10.1002/cbic.201402394

文献信息

• A Membrane-Bound Prenyltransferase Catalyzes the O-Prenylation of 1,6-Dihydroxyphenazine in the Marine Bacterium<i>Streptomyces</i>sp. CNQ-509
  作者：Philipp Zeyhle、Judith S. Bauer、Marco Steimle、Franziska Leipoldt、Manuela Rösch、Jörn Kalinowski、Harald Gross、Lutz Heide

  DOI：10.1002/cbic.201402394

  日期：2014.11.3

  AbstractStreptomyces sp. CNQ‐509 produces the rare O‐prenylated phenazines marinophenazines A and B. To identify the enzyme catalyzing the O‐prenyl transfer in marinophenazine biosynthesis, we sequenced the genome of S. sp. CNQ‐509. This led to the identification of two genomic loci harboring putative phenazine biosynthesis genes. The first locus contains orthologues for all seven genes involved in phenazine‐1‐carboxylic acid biosynthesis in pseudomonads. The second locus contains two known phenazine biosynthesis genes and a putative prenyltransferase gene termed cnqPT1. cnqPT1 codes for a membrane protein with sequence similarity to the prenyltransferase UbiA of ubiquinone biosynthesis. The enzyme CnqPT1 was identified as a 1,6‐dihydroxyphenazine geranyltransferase, which catalyzes the CO bond formation between C‐1 of the geranyl moiety and O‐6 of the phenazine scaffold. CnqPT1 is the first example of a prenyltransferase catalyzing O‐prenyl transfer to a phenazine.