RM 80b

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: RM 80b
• 化学式: C₂₀H₁₄O₇
• 分子量: 366.327
• InChiKey: CHYSJOVJYNCRGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  121.11
• 氢给体数：
  3.0
• 氢受体数：
  7.0

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 RM 80b 、
  参考文献：
  名称：

  Engineered Biosynthesis of Novel Polyketides: Analysis of tcmN Function in Tetracenomycin Biosynthesis

  摘要：

  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.

  DOI：

  10.1021/ja00131a001

文献信息

• Processes and host cells for genome, pathway, and biomolecular engineering
  申请人：enEvolv, Inc.

  公开号：US10370654B2

  公开（公告）日：2019-08-06

  The present disclosure provides compositions and methods for genomic engineering.

  本公开提供了基因组工程的组合物和方法。
• PROCESSES AND HOST CELLS FOR GENOME, PATHWAY, AND BIOMOLECULAR ENGINEERING
  申请人：ENEVOLV, INC.

  公开号：US20160186168A1

  公开（公告）日：2016-06-30

  The present disclosure provides compositions and methods for genomic engineering.
• US9944925B2
  申请人：——

  公开号：US9944925B2

  公开（公告）日：2018-04-17
• 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.