[(1S,2S,5S,6R,10S,11R,13S,14R,15R)-13-butanoyloxy-5-(2-diazoacetyl)oxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] butanoate | 150537-62-5

• 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,5S,6R,10S,11R,13S,14R,15R)-13-butanoyloxy-5-(2-diazoacetyl)oxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] butanoate
• CAS: 150537-62-5
• 化学式: C₃₀H₄₂N₂O₉
• 分子量: 574.671
• InChiKey: LUYLEBIKLHKRJR-YDTGDEFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  142
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(1S,2S,5S,6R,10S,11R,13S,14R,15R)-13-butanoyloxy-5-(2-diazoacetyl)oxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-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， 反应 0.5h， 以71%的产率得到[(1S,2S,5S,6R,10S,11R,13S,14R,15R)-13-butanoyloxy-5-(2-diazoacetyl)oxy-8-formyl-1,6-dihydroxy-4,12,12,15-tetramethyl-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：

  (3-deoxo-3β-glycyloxyphorbol 12,13,20-tributyrate) 在 barium dihydroxide 、 硫酸 、 sodium nitrite 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 [(1S,2S,5S,6R,10S,11R,13S,14R,15R)-13-butanoyloxy-5-(2-diazoacetyl)oxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-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

文献信息

• Synthesis and binding of photoaffinity ligand candidates for protein kinase C
  作者：Paul A. Wender、Kazuhiro Irie、Benjamin L. Miller

  DOI：10.1021/jo00068a001

  日期：1993.7

  Our observation that protein kinase C binding is retained by phorbol esters modified at the C-3 position has led to the design of a new class of photoaffinity ligand candidates. The first members of this class, esters 3 and 4, were synthesized from phorbol and found to bind to PKC with high affinity; the solution photochemistry of 3 leads predominantly to insertion products, as required for its use as a PKC receptor probe.