cyanosporaside C | 1423138-34-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: cyanosporaside C
• 英文别名: [(2R,3S,5S,6S)-6-[[(1S,8bR)-5-chloro-7-(cyanomethyl)-1-hydroxy-1H-cyclopenta[a]inden-8b-yl]oxy]-5-hydroxy-2,3-dimethyl-4-oxooxan-3-yl] acetate
• CAS: 1423138-34-4
• 化学式: C₂₃H₂₂ClNO₇
• 分子量: 459.883
• InChiKey: JDWXQXVZKUSNSM-NYUUDHSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  cyanosporaside C 、 甲氧基-三氟甲基苯 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 12.0h， 生成 cyanosporaside C
  参考文献：
  名称：

  Structures and Comparative Characterization of Biosynthetic Gene Clusters for Cyanosporasides, Enediyne-Derived Natural Products from Marine Actinomycetes

  摘要：

  Cyanosporasides are marine bacterial natural products containing a chlorinated cyclopenta[a]indene core of suspected enediyne polyketide biosynthetic origin. Herein, we report the isolation and characterization of novel cyanosporasides C-F (3-6) from the marine actinomycetes Salinispora pacifica CNS-143 and Streptomyces sp. CNT-179, highlighted by the unprecedented C-2' N-acetylcysteamine functionalized hexose group of 6. Cloning, sequencing, and mutagenesis of homologous similar to 50 kb cyanosporaside biosynthetic gene clusters from both bacteria afforded the first genetic evidence supporting cyanosporaside's enediyne, and thereby p-benzyne biradical, biosynthetic origin and revealed the molecular basis for nitrile and glycosyl functionalization. This study provides new opportunities for bioengineering of enediyne derivatives and expands the structural diversity afforded by enediyne gene clusters.

  DOI：

  10.1021/ja311065v