[(1S,2S,6R,10S,11R,13S,14R,15R)-13-(2-diazoacetyl)oxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] butanoate | 174201-87-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [(1S,2S,6R,10S,11R,13S,14R,15R)-13-(2-diazoacetyl)oxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] butanoate
• CAS: 174201-87-7
• 化学式: C₂₆H₃₄N₂O₈
• 分子量: 502.565
• InChiKey: NLFCPVLCJSDCLG-BPNNYVJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(1S,2S,6R,10S,11R,13S,14R,15R)-13-(2-diazoacetyl)oxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] butanoate 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 以47%的产率得到[(1S,2S,6R,10S,11R,13S,14R,15R)-13-(2-diazoacetyl)oxy-8-formyl-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] butanoate
  参考文献：
  名称：

  Synthesis and Characterization of New Photolabile Phorbol Esters for Affinity Labeling of Protein Kinase C

  摘要：

  Three new photolabile phorbol esters (3, 6, and 9) with a diazoacetyl group at positions 3, 12, and 13, respectively, have been synthesized from phorbol (1a) and found to bind with significant affinity to the peptide (peptide C) incorporating the phorbol ester-binding domain of protein kinase C. As required for its use as a protein kinase C receptor probe, the solution photochemistry of 3 led predominantly to insertion products. Tritium labeling of these probes at C-20 was accomplished by oxidation with activated manganese dioxide to the C-20 aldehyde and subsequent H-3-labeled sodium borohydride reduction. Initial affinity labeling studies showed that probes 6 and 9 labeled peptide C, suggesting that the introduction of a photolabile group into position 12 or 13 of the phorbol esters could be used to identify the structural features of PKC involved in its binding to activators.

  DOI：

  10.1021/jo9512867
• 作为产物：
  描述：

  phorbol 20-trityl 在 盐酸 、 4-二甲氨基吡啶 、 barium dihydroxide 、 高氯酸 、 硫酸 、 溶剂黄146 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 7.33h， 生成 [(1S,2S,6R,10S,11R,13S,14R,15R)-13-(2-diazoacetyl)oxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] butanoate
  参考文献：
  名称：

  Synthesis and Characterization of New Photolabile Phorbol Esters for Affinity Labeling of Protein Kinase C

  摘要：

  Three new photolabile phorbol esters (3, 6, and 9) with a diazoacetyl group at positions 3, 12, and 13, respectively, have been synthesized from phorbol (1a) and found to bind with significant affinity to the peptide (peptide C) incorporating the phorbol ester-binding domain of protein kinase C. As required for its use as a protein kinase C receptor probe, the solution photochemistry of 3 led predominantly to insertion products. Tritium labeling of these probes at C-20 was accomplished by oxidation with activated manganese dioxide to the C-20 aldehyde and subsequent H-3-labeled sodium borohydride reduction. Initial affinity labeling studies showed that probes 6 and 9 labeled peptide C, suggesting that the introduction of a photolabile group into position 12 or 13 of the phorbol esters could be used to identify the structural features of PKC involved in its binding to activators.

  DOI：

  10.1021/jo9512867