| 1191041-51-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• CAS: 1191041-51-6
• 化学式: C₁₈H₃₂O₆
• 分子量: 344.448
• InChiKey: KWLXQZQQOOQPCR-LECNZMIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.91
• 重原子数：
  24.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  111.9
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  、 methylmalonyl CoA 在 NADPH 、 3,3,3-膦三基三丙酸 、 乙二胺四乙酸 、 pikromycin AIII-TE 、 sodium chloride 作用下， 以 水 、 二甲基亚砜 、 甘油 为溶剂， 反应 24.0h， 生成 (3R,4S,5S,7R,11R,12R)-12-ethyl-4-hydroxy-3,5,7,11-tetramethyl-1-oxacyclododec-9-ene-2,8-dione 、 (8R,9S)-8,9-dihydro-8-methyl-9-hydroxy-10-deoxymethynolide
  参考文献：
  名称：

  Synthesis and Biochemical Analysis of Complex Chain-Elongation Intermediates for Interrogation of Molecular Specificity in the Erythromycin and Pikromycin Polyketide Synthases

  摘要：

  The 6-deoxyerythronolide B synthase (DEBS) and pikromycin (Pik) polyketide synthase (PKS) are unique multifunctional enzyme systems that are responsible for the biosynthesis of the erythromycin and pikromycin 14-membered ring aglycones, respectively. Together, these natural product biosynthetic systems provide excellent platforms to examine the fundamental structural and catalytic elements that govern polyketide assembly, processing, and macrocyclization. In these studies, the native pentaketide intermediate for DEBS was synthesized and employed for in vitro chemoenzymatic synthesis of macrolactone products in engineered monomodules Ery5, Ery5-TE, and Ery6. A comparative analysis was performed with the corresponding Pik module 5 (PikAIII) and module 6 (PikAIV), dissecting key similarities and differences between these highly related PKSs. The data revealed that individual modules in the DEBS and Pik PKSs possess distinctive molecular selectivity profiles and suggest that substrate recognition has evolved unique characteristics in each system.

  DOI：

  10.1021/ja9060596
• 作为产物：
  描述：

  S-(2-acetamidoethyl) (2S,4R,6R,7S,8S,9R)-7,9-dihydroxy-2,4,6,8-tetramethyl-5-oxoundecanethioate 、 methylmalonyl CoA 在 NADPH 、 3,3,3-膦三基三丙酸 、 乙二胺四乙酸 、 Ery₅-TE 、 sodium chloride 作用下， 以 水 、 二甲基亚砜 、 甘油 为溶剂， 反应 24.0h， 生成 、 (8R,9S)-8,9-dihydro-8-methyl-9-hydroxy-10-deoxymethynolide
  参考文献：
  名称：

  Synthesis and Biochemical Analysis of Complex Chain-Elongation Intermediates for Interrogation of Molecular Specificity in the Erythromycin and Pikromycin Polyketide Synthases

  摘要：

  The 6-deoxyerythronolide B synthase (DEBS) and pikromycin (Pik) polyketide synthase (PKS) are unique multifunctional enzyme systems that are responsible for the biosynthesis of the erythromycin and pikromycin 14-membered ring aglycones, respectively. Together, these natural product biosynthetic systems provide excellent platforms to examine the fundamental structural and catalytic elements that govern polyketide assembly, processing, and macrocyclization. In these studies, the native pentaketide intermediate for DEBS was synthesized and employed for in vitro chemoenzymatic synthesis of macrolactone products in engineered monomodules Ery5, Ery5-TE, and Ery6. A comparative analysis was performed with the corresponding Pik module 5 (PikAIII) and module 6 (PikAIV), dissecting key similarities and differences between these highly related PKSs. The data revealed that individual modules in the DEBS and Pik PKSs possess distinctive molecular selectivity profiles and suggest that substrate recognition has evolved unique characteristics in each system.

  DOI：

  10.1021/ja9060596