SEK 15

• 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: SEK 15
• 英文别名: 2-[[2-(2,4-dihydroxy-6-methylbenzoyl)-3,5-dihydroxyphenyl]methyl]-6-hydroxypyran-4-one
• 化学式: C₂₀H₁₆O₈
• 分子量: 384.342
• InChiKey: HSOLPAFROQCEQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  148.43
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  乙酰辅酶A 、 丙二酰辅酶A-钠盐 生成 SEK 15 、 4,5,7-trihydroxy-1-(6-hydroxy-4-oxopyran-2-yl)-2-methylanthracene-9,10-dione
  参考文献：
  名称：

  Streptomyces glaucescens tcmKL 聚酮化合物合酶和 tcmN 聚酮化合物环化酶基因控制芳香族聚酮化合物的大小和形状

  摘要：

  通过在各种突变体或异源宿主中组合表达四烯霉素 (tcm) 和放线菌素 (act) 聚酮合酶基因的成分，分析了 I1 型聚酮合酶的机制。重组生物体产生的代谢物的结构分析为剖析 II 型 PKS 的各个成分的功能提供了证据。与包含 tcmK 和 actl-ORF2 或 actl-ORF1 和 tcmL 基因的 S. glaucescens TcmK 和 TcmL 突变体和构建体的互补研究表明，编码 j3-酮酰基 1:酰基载体蛋白合酶和链长因子的异源基因对通常是（但并非总是）不起作用。从带有 actl-ORF1、actl-ORF2 和 tcmM (pWHM766) 或 tcd、actl-ORF1、actl-ORF2 和 tcmM (pWHM768) 的菌株中分离出八酮化合物 6 和 7，来自带有 tcmK、tcmL 和 tcmM (pELE37) 或 tcd 、tcmK、tcmL 和 tcmM (pWHM731)

  DOI：

  10.1021/ja00131a002

文献信息

• Engineered Biosynthesis of Novel Polyketides: Analysis of tcmN Function in Tetracenomycin Biosynthesis
  作者：Robert McDaniel、C. R. Hutchinson、Chaitan Khosla

  DOI：10.1021/ja00131a001

  日期：1995.7

  Two proteins, encoded by the tcmJ and tcmN genes, have been previously implicated in early cyclization steps in the biosynthesis of the aromatic polyketide tetracenomycin. In order to elucidate the function of these enzymes and to evaluate their potential for generating novel polyketides, several tcmJ- and tcmN-containing recombinant polyketide synthase (PKS) gene clusters were constructed and analyzed in vivo. These constructs led to the expression of combinations of the TcmJ and TcmN proteins with subunits from the actinorhodin (act) and tetracenomycin (tcm) PKSs, responsible for the biosynthesis of different polyketide backbones. In addition to three novel polyketides, RM77 (3), RM80 (4), and RM806b (5), which are characterized here, several previously isolated polyketides were produced. While results for TcmJ were inconclusive, comparison of the new molecules to other polyketide structures has allowed us to propose two functions for TcmN. First, consistent with earlier predictions [McDaniel, R.; Ebert-Khosla, S.; Fu, H.; Hopwood, D. A.; Khosla, C. Proc. Natl. Acad. Sci; U.S.A. 1994, 91, 11542-11546], the TcmN protein influences the regiospecificity of the intramolecular aldol condensation that forms the first ring. Second, the protein appears to catalyze the aromatization of the second ring, and is deduced to be a second ring aromatase. The inability of TcmN to have any affect on C-9 reduced backbones suggests that ketoreduction occurs prior to cyclization of the first ring in reduced polyketides. The analysis of TcmN extends the use of genetically engineered PKSs for novel polyketide design and biosynthesis.
• The Streptomyces glaucescens tcmKL polyketide synthase and tcmN polyketide cyclase genes govern the size and shape of aromatic polyketides
  作者：B. Shen、R. G. Summers、E. Wendt-Pienkowski、C. R. Hutchinson

  DOI：10.1021/ja00131a002

  日期：1995.7

  large and diverse family of secondary metabolites found in bacteria, fungi, and plants.’ Many of them are clinically valuable antibiotics or chemotherapeutic agents or have other useful pharmacological activities (immunosuppressive, antiparasitic, insecticidal, etc).2 Ever since Birch3 outlined his “acetate hypothesis” in the early 1950s that polyketides could be biosynthetically derived from short fatty

  通过在各种突变体或异源宿主中组合表达四烯霉素 (tcm) 和放线菌素 (act) 聚酮合酶基因的成分，分析了 I1 型聚酮合酶的机制。重组生物体产生的代谢物的结构分析为剖析 II 型 PKS 的各个成分的功能提供了证据。与包含 tcmK 和 actl-ORF2 或 actl-ORF1 和 tcmL 基因的 S. glaucescens TcmK 和 TcmL 突变体和构建体的互补研究表明，编码 j3-酮酰基 1:酰基载体蛋白合酶和链长因子的异源基因对通常是（但并非总是）不起作用。从带有 actl-ORF1、actl-ORF2 和 tcmM (pWHM766) 或 tcd、actl-ORF1、actl-ORF2 和 tcmM (pWHM768) 的菌株中分离出八酮化合物 6 和 7，来自带有 tcmK、tcmL 和 tcmM (pELE37) 或 tcd 、tcmK、tcmL 和 tcmM (pWHM731)