(3E,5E,7E,9E,11E,13E)-pentadeca-3,5,7,9,11,13-hexaen-2-one | 1187429-73-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3E,5E,7E,9E,11E,13E)-pentadeca-3,5,7,9,11,13-hexaen-2-one
• CAS: 1187429-73-7
• 化学式: C₁₅H₁₈O
• 分子量: 214.307
• InChiKey: IKKRHADMXZRWGK-IDFWPVMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (2E,4E,6E,8E,10E)-dodeca-2,4,6,8,10-pentaenal 、 丙酮基膦酸二甲酯 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以66%的产率得到(3E,5E,7E,9E,11E,13E)-pentadeca-3,5,7,9,11,13-hexaen-2-one
  参考文献：
  名称：

  9元和10元烯二炔生物合成中的迭代聚酮化合物合酶的产物。

  摘要：

  研究了三种烯二炔天然产物的生物合成途径中的迭代聚酮化合物合酶。结果确定了全反式共轭十五碳烯是PKS共享的唯一主要产物。通过证明形成不同的副产物，实验进一步揭示了PKS之间的某些内在差异。

  DOI：

  10.1039/b916751j

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.
• Products of the iterative polyketide synthases in 9- and 10-membered enediyne biosynthesis
  作者：Huihua Sun、Rong Kong、Di Zhu、Min Lu、Qiang Ji、Chong Wai Liew、Julien Lescar、Guofu Zhong、Zhao-Xun Liang

  DOI：10.1039/b916751j

  日期：——

  The iterative polyketide synthases from the biosynthetic pathways of three enediyne natural products were examined. The results established the all-trans conjugated pentadecaheptanene as the only major product shared by the PKSs. The experiments further revealed some intrinsic differences among the PKSs by demonstrating the formation of different by-products.

  研究了三种烯二炔天然产物的生物合成途径中的迭代聚酮化合物合酶。结果确定了全反式共轭十五碳烯是PKS共享的唯一主要产物。通过证明形成不同的副产物，实验进一步揭示了PKS之间的某些内在差异。