1,3E,5E,7E,9E,11E,13E-pentadecaheptaene | 676579-01-4

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 1,3E,5E,7E,9E,11E,13E-pentadecaheptaene
• 英文别名: (3E,5E,7E,9E,11E,13E)-pentadeca-1,3,5,7,9,11,13-heptaene
• CAS: 676579-01-4
• 化学式: C₁₅H₁₈
• 分子量: 198.308
• InChiKey: CETJIWVTDUCJAH-MOVKVLISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  丙二酰辅酶A-钠盐 在 calicheamicin polyketide synthase CalE₈ 、 calicheamicin thioesterase CalE₇ 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 甘油 为溶剂， 反应 2.0h， 生成 4-羟基-6-甲基-2-吡喃酮 、 4-羟基-6-(1-丙烯基)-吡喃-2-酮 、 4-hydroxy-6-((1E,3E)-penta-1,3-dien-1-yl)-2H-pyran-2-one 、 1,3E,5E,7E,9E,11E,13E-pentadecaheptaene 、 6-((1E,3E,5E)-hepta-1,3,5-trien-1-yl)-4-hydroxy-2H-pyran-2-one 、 (3E,5E,7E,9E,11E,13E)-pentadeca-3,5,7,9,11,13-hexaen-2-one 、 3-oxohexadeca-4,6,8,10,12,14-hexaenoic acid
  参考文献：
  名称：

  Production of Octaketide Polyenes by the Calicheamicin Polyketide Synthase CalE8: Implications for the Biosynthesis of Enediyne Core Structures

  摘要：

  Enediyne antibiotics are categorized according to the presence of either a 9- or 10-membered ring within their polyketide-derived core structures. Recent literature reports have favored the notion that biosynthetic divergence of the two structural families is determined by the enediyne polyketide synthases (PKSs) alone. We now disclose the simultaneous in vitro production of three octaketide polyenes by biosynthetic enzymes for the 10-membered enediyne calicheamicin Y-1(1), including the elusive beta-keto acid precursor to a previously described C15 methyl hexaenone. Alongside these two polyene products, we have additionally detected a hydrocarbon heptaene previously isolated only from 9-membered enediyne systems. The discovery of the heptaene in the calicheamicin system promotes a more convergent model for the early steps of enediyne biosynthesis. Furthermore, the synthesis of this set of octaketides by the enediyne PKS CalE8 and thioesterase CalE7 suggests, in contrast to recent biosynthetic proposals, that accessory enzymes may be necessary to initiate differentiation to 9- or 10-membered enediyne precursors,;1 either by modulation of enediyne PKS activity or by interception and modification of polyketide chain-extension intermediates.

  DOI：

  10.1021/ja904391r

文献信息

• Production of Octaketide Polyenes by the Calicheamicin Polyketide Synthase CalE8: Implications for the Biosynthesis of Enediyne Core Structures
  作者：Katherine Belecki、Jason M. Crawford、Craig A. Townsend

  DOI：10.1021/ja904391r

  日期：2009.9.9

  Enediyne antibiotics are categorized according to the presence of either a 9- or 10-membered ring within their polyketide-derived core structures. Recent literature reports have favored the notion that biosynthetic divergence of the two structural families is determined by the enediyne polyketide synthases (PKSs) alone. We now disclose the simultaneous in vitro production of three octaketide polyenes by biosynthetic enzymes for the 10-membered enediyne calicheamicin Y-1(1), including the elusive beta-keto acid precursor to a previously described C15 methyl hexaenone. Alongside these two polyene products, we have additionally detected a hydrocarbon heptaene previously isolated only from 9-membered enediyne systems. The discovery of the heptaene in the calicheamicin system promotes a more convergent model for the early steps of enediyne biosynthesis. Furthermore, the synthesis of this set of octaketides by the enediyne PKS CalE8 and thioesterase CalE7 suggests, in contrast to recent biosynthetic proposals, that accessory enzymes may be necessary to initiate differentiation to 9- or 10-membered enediyne precursors,;1 either by modulation of enediyne PKS activity or by interception and modification of polyketide chain-extension intermediates.