decinnamoyltaxinine J | 84652-33-5

• 英文名称: decinnamoyltaxinine J
• 英文别名: [(1R,2R,3R,5S,7S,8S,9R,10R,13S)-2,7,9,10-tetraacetyloxy-5-hydroxy-8,12,15,15-tetramethyl-4-methylidene-13-tricyclo[9.3.1.03,8]pentadec-11-enyl] acetate
• CAS: 84652-33-5
• 化学式: C₃₀H₄₂O₁₁
• 分子量: 578.657
• InChiKey: NTRHFSRAAXRZLC-FJANQRQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  152
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  decinnamoyltaxinine J 在 cytochrome P₄₅₀ enzyme from Taxus-media oxetane synthase 作用下， 以40 %的产率得到[(1'R,2R,2'R,3'R,5'S,7'S,8'S,9'R,10'R,13'S)-2',7',9',10'-tetraacetyloxy-5'-hydroxy-8',12',15',15'-tetramethylspiro[oxirane-2,4'-tricyclo[9.3.1.03,8]pentadec-11-ene]-13'-yl] acetate
  参考文献：
  名称：

  A Cytochrome P450 Enzyme Catalyses Oxetane Ring Formation in Paclitaxel Biosynthesis

  摘要：

  Oxetane synthase (TmCYP1), a novel cytochrome P450 enzyme from Taxus×media cell cultures, has been functionally characterized to efficiently catalyse the formation of the oxetane ring in tetracyclic taxoids. Transient expression of TmCYP1 in Nicotiana benthamiana using 2α,5α,7β,9α,10β,13α‐hexaacetoxytaxa‐4(20),11(12)‐diene (1) as a substrate led to the production of a major oxetane derivative, 1β‐dehydroxybaccatin IV (1 a), and a minor 4β,20‐epoxide derivative, baccatin I (1 b). However, feeding the substrate decinnamoyltaxinine J (2), a 5‐deacetylated derivative of 1, yielded only 5α‐deacetylbaccatin I (2 b), a 4β,20‐epoxide. A possible reaction mechanism was proposed on the basis of substrate‐feeding, 2H and 18O isotope labelling experiments, and density functional theory calculations. This reaction could be an intramolecular oxidation‐acetoxyl rearrangement and the construction of the oxetane ring may occur through a concerted process; however, the 4β,20‐epoxide might be a shunt product. In this process, the C5‐O‐acetyl group in substrate is crucial for the oxetane ring formation but not for the 4(20)‐epoxy ring formation by TmCYP1. These findings provide a better understanding of the enzymatic formation of the oxetane ring in paclitaxel biosynthesis.

  DOI：

  10.1002/anie.202407070
• 作为产物：
  描述：

  triacetoxy-7β,9α,10β trihydroxy-2α,5α,13α taxadiene-4(20),11 、 乙酸酐 在 吡啶 作用下， 反应 48.0h， 以1.2 mg的产率得到decinnamoyltaxinine J
  参考文献：
  名称：

  Ettouati, Laurent; Ahond, Alain; Convert, Odile, Bulletin de la Societe Chimique de France, 1989, # 5, p. 687 - 694

  摘要：

  DOI：

文献信息

• ETTOUATI, LAURENT;AHOND, ALAIN;CONVERT, ODILE;POUPAT, CHRISTIANE;POTIER, +, BULL. SOC. CHIM. FR.,(1989) N, C. 687-694
  作者：ETTOUATI, LAURENT、AHOND, ALAIN、CONVERT, ODILE、POUPAT, CHRISTIANE、POTIER, +

  DOI：——

  日期：——