N-methylanthraniloyl-CoA

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-methylanthraniloyl-CoA
• 英文别名: S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] 2-(methylamino)benzenecarbothioate
• 化学式: C₂₉H₄₃N₈O₁₇P₃S
• 分子量: 900.691
• InChiKey: DYCZFHXLKCLDQL-SXQYHYLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  58
• 可旋转键数：
  22
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  401
• 氢给体数：
  10
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  N-methylanthraniloyl-CoA 、 丙二酰辅酶A-钠盐 在 Huperzia serrata type III polyketide synthase 作用下， 以 aq. phosphate buffer 为溶剂， 反应 12.0h， 以18.7%的产率得到4-羟基-N-甲基-2-喹啉
  参考文献：
  名称：

  Synthesis of Unnatural 2-Substituted Quinolones and 1,3-Diketones by a Member of Type III Polyketide Synthases from Huperzia serrata

  摘要：

  A curcuminoids, benzalacetone-, and quinolone-producing type III polyketide synthase (HsPKS3) from Huperzia serrata uniquely catalyzes the formation of unnatural 2-substituted quinolones and 1,3-diketones via head-to-head condensation of two completely different substrates. The broad range of substrate tolerance of HsPKS3 facilitates accessing structurally diverse 2-substituted quinolones and 1,3-diketones.

  DOI：

  10.1021/acs.orglett.6b01501

文献信息

• Enzymatic Formation of Quinolone Alkaloids by a Plant Type III Polyketide Synthase
  作者：Ikuro Abe、Tsuyoshi Abe、Kiyofumi Wanibuchi、Hiroshi Noguchi

  DOI：10.1021/ol0625233

  日期：2006.12.1

  Benzalacetone synthase from Rheum palmatum efficiently catalyzed condensation of N-methylanthraniloyl-CoA (or anthraniloyl-CoA) with malonyl-CoA (or methylmalonyl-CoA) to produce 4-hydroxy-2(1H)-quinolones, a novel alkaloidal scaffold produced by a type III polyketide synthase (PKS). Manipulation of the functionally divergent type III PKSs by a nonphysiological substrate thus provides an efficient method for production of pharmaceutically important quinolone alkaloids.
• Cloning and Structure-Function Analyses of Quinolone- and Acridone-producing Novel Type III Polyketide Synthases from Citrus microcarpa
  作者：Takahiro Mori、Yoshihiko Shimokawa、Takashi Matsui、Keishi Kinjo、Ryohei Kato、Hiroshi Noguchi、Shigetoshi Sugio、Hiroyuki Morita、Ikuro Abe

  DOI：10.1074/jbc.m113.493155

  日期：2013.10

  Two novel type III polyketide synthases, quinolone synthase (QNS) and acridone synthase (ACS), were cloned from Citrus microcarpa (Rutaceae). The deduced amino acid sequence of C. microcarpa QNS is unique, and it shared only 56-60% identities with C. microcarpa ACS, Medicago sativa chalcone synthase (CHS), and the previously reported Aegle marmelos QNS. In contrast to the quinolone- and acridone-producing A. marmelos QNS, C. microcarpa QNS produces 4-hydroxy-N-methylquinolone as the single product by the one-step condensation of N-methylanthraniloyl-CoA and malonyl-CoA. However, C. microcarpa ACS shows broad substrate specificities and produces not only acridone and quinolone but also chalcone, benzophenone, and phloroglucinol from 4-coumaroyl-CoA, benzoyl-CoA, and hexanoyl-CoA, respectively. Furthermore, the x-ray crystal structures of C. microcarpa QNS and ACS, solved at 2.47- and 2.35- resolutions, respectively, revealed wide active site entrances in both enzymes. The wide active site entrances thus provide sufficient space to facilitate the binding of the bulky N-methylanthraniloyl-CoA within the catalytic centers. However, the active site cavity volume of C. microcarpa ACS (760 (3)) is almost as large as that of M. sativa CHS (750 (3)), and ACS produces acridone by employing an active site cavity and catalytic machinery similar to those of CHS. In contrast, the cavity of C. microcarpa QNS (290 (3)) is significantly smaller, which makes this enzyme produce the diketide quinolone. These results as well as mutagenesis analyses provided the first structural bases for the anthranilate-derived production of the quinolone and acridone alkaloid by type III polyketide synthases.
• MICROORGANISM PRODUCTION OF HIGH-VALVE CHEMICAL PRODUCTS, AND RELATED COMPOSITIONS, METHODS AND SYSTEMS
  申请人：OPX Biotechnologies Inc.

  公开号：EP2529023A1

  公开（公告）日：2012-12-05
• MICROBIAL PRODUCTION OF CHEMICAL PRODUCTS AND RELATED COMPOSITIONS, METHODS AND SYSTEMS
  申请人：OPX Biotechnologies Inc.

  公开号：EP2689020A1

  公开（公告）日：2014-01-29
• MICROORGANISM PRODUCTION OF HIGH-VALUE CHEMICAL PRODUCTS, AND RELATED COMPOSITIONS, METHODS AND SYSTEMS
  申请人：Lynch Michael D.

  公开号：US20130122541A1

  公开（公告）日：2013-05-16

  This invention relates to metabolically engineered microorganism strains, such as bacterial strains, in which there is an increased utilization of malonyl-CoA for production of a chemical product, which includes polyketides and 3-hydroxypropionic acid.