(7S,13S,16S,19S)-27-hydroxy-16-methyl-7-(methylamino)-19-propan-2-yl-2,4,9,15,18,21-hexazatetracyclo[22.3.1.12,5.09,13]nonacosa-1(27),3,5(29),24(28),25-pentaene-8,14,17,20-tetrone | 1192262-06-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (7S,13S,16S,19S)-27-hydroxy-16-methyl-7-(methylamino)-19-propan-2-yl-2,4,9,15,18,21-hexazatetracyclo[22.3.1.12,5.09,13]nonacosa-1(27),3,5(29),24(28),25-pentaene-8,14,17,20-tetrone
• CAS: 1192262-06-8
• 化学式: C₂₈H₃₉N₇O₅
• 分子量: 553.662
• InChiKey: MYPYMXIMQZVVHP-QBVRBKIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  40
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  158
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  benzyl N-[(7S,13S,16S,19S)-27-hydroxy-16-methyl-8,14,17,20-tetraoxo-19-propan-2-yl-2,4,9,15,18,21-hexazatetracyclo[22.3.1.12,5.09,13]nonacosa-1(27),3,5(29),24(28),25-pentaen-7-yl]-N-methylcarbamate;2,2,2-trifluoroacetic acid 在 氢气 、 palladium(II) hydroxide 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以95%的产率得到(7S,13S,16S,19S)-27-hydroxy-16-methyl-7-(methylamino)-19-propan-2-yl-2,4,9,15,18,21-hexazatetracyclo[22.3.1.12,5.09,13]nonacosa-1(27),3,5(29),24(28),25-pentaene-8,14,17,20-tetrone
  参考文献：
  名称：

  Synthesis of a Cyclic Pentapeptide Mimic of the Active Site His-Tyr Cofactor of Cytochrome c Oxidase

  摘要：

  Arylboronic acid based technology provides a mild, regioselective, and nontoxic N-arylation procedure for accessing the Unusual N-arylated side chain histidine found in the active site of cytochrome c oxidase (CcO) The N-arylated histidine is elaborated to the complete cytochrome c oxidase cyclic pentapeptide cofactor. Molecular modeling of the cofactor provides insight into the dynamic character of the N-aryl bond.

  DOI：

  10.1021/jo901744y

文献信息

• Synthesis of a Cyclic Pentapeptide Mimic of the Active Site His-Tyr Cofactor of Cytochrome <i>c</i> Oxidase
  作者：Maximillian E. Mahoney、Allen Oliver、Ólöf Einarsdóttir、Joseph P. Konopelski

  DOI：10.1021/jo901744y

  日期：2009.11.6

  Arylboronic acid based technology provides a mild, regioselective, and nontoxic N-arylation procedure for accessing the Unusual N-arylated side chain histidine found in the active site of cytochrome c oxidase (CcO) The N-arylated histidine is elaborated to the complete cytochrome c oxidase cyclic pentapeptide cofactor. Molecular modeling of the cofactor provides insight into the dynamic character of the N-aryl bond.