[3',7-D6]laudanosine | 1242242-84-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: [3',7-D6]laudanosine
• CAS: 1242242-84-7
• 化学式: C₂₁H₂₇NO₄
• 分子量: 363.402
• InChiKey: KGPAYJZAMGEDIQ-LJSLLGHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  40.16
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  氘代碘甲烷 、 (+)-reticuline N-oxide 在 potassium hydroxide 、 sodium hydrogensulfite 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 5.0h， 以10%的产率得到(S)-劳丹碱
  参考文献：
  名称：

  The biosynthesis of papaverine proceeds via (S)-reticuline

  摘要：

  Papaverine is one of the earliest opium alkaloids for which a biosynthetic hypothesis was developed on theoretical grounds. Norlaudanosoline (=tetrahydropapaveroline) was claimed as the immediate precursor alkaloid for a multitude of nitrogen containing plant metabolites. This tetrahydroxylated compound was proposed to be fully O-methylated. The resulting tetrahydropapaverine should then aromatize to papaverine. In view of experimental data, this pathway has to be revised. Precursor administration to 8-day-old seedlings of Papaver followed by direct examination of the metabolic fate of the stable-isotope-labeled precursors in the total plant extract, without further purification of the metabolites, led to elucidation of the papaverine pathway in vivo. The central and earliest benzylisoquinoline alkaloid is not the tetraoxygenated norlaudanosoline, but instead the trihydroxylated norcoclaurine that is further converted into (S)-reticuline, the established precursor for poppy alkaloids. The papaverine pathway is opened by the methylation of (S)-reticuline to generate (S)-laudanine. A second methylation at the 3' position of laudanine leads to laudanosine, both known alkaloids from the opium poppy. Subsequent N-demethylation of laudanosine yields the known precursor of papaverine: tetrahydropapaverine. Inspection of the subsequent aromatization reaction established the presence of an intermediate, 1,2-dihydropapaverine, which has been characterized. The final step to papaverine is dehydrogenation of the 1,2-bond, yielding the target compound papaverine. We conclusively show herein that the previously claimed norreticuline does not play a role in the biosynthesis of papaverine. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2010.04.022