Lysolipin I

• 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: Lysolipin I
• 英文别名: (7S,8S,12R,13S)-22-chloro-3,8,28-trihydroxy-7,12,21-trimethoxy-6-methyl-14,16,19-trioxa-6-azaheptacyclo[15.11.1.02,11.04,9.013,29.018,27.020,25]nonacosa-1(29),2,4(9),10,17,20(25),21,23,27-nonaene-5,26-dione
• 化学式: C₂₉H₂₄ClNO₁₁
• 分子量: 597.963
• InChiKey: NEOMIZJYHXSRLV-ZIITWBKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  42
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  153
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  Lysolipin X 生成 Lysolipin I
  参考文献：
  名称：

  Biosynthetic studies on the xanthone antibiotics lysolipins X and I

  摘要：

  Feeding experiments with C-13 and O-18-labeled precursors revealed that the molecular framework of the polycyclic xanthone antibiotics, the lysolipins X (1) and I (2), is derived from the polyketide pathway (12 malonate unites), the C-1 pool (methionine), molecular oxygen, and the nitrogen pool. Surprisingly, and intact malonate moiety serves as the three-carbon starter unit of the polyketide backbone, and 9 of the 12 oxygen atoms of 1 originate from molecular oxygen, including both of the xanthone oxygen atoms. The orientation of the malonate unit incorporated intact into lysolipin is unique and opposite from those in tetracycline and cycloheximide, i.e., the activated carbon of malonyl CoA is bound to the nitrogen of the lysolipin isoquinoline ring and the CO2-derived carbon serves as the starter of the polyketide chain. From the biogenetic origin of the oxygen atoms several unusual prearomatic deoxygenation steps early in the biosynthesis have to be postulated.

  DOI：

  10.1021/jo00087a021