(2S)-1-[(2R,3R)-3-[[(2S)-1-[2-[[2-[[(2S)-1-[(2R,3R)-3-[[(2S)-1-[2-[(2-aminoacetyl)-methylamino]acetyl]piperidine-2-carbonyl]amino]-2-(phenylmethoxycarbonylamino)butanoyl]piperidine-2-carbonyl]amino]acetyl]-methylamino]acetyl]piperidine-2-carbonyl]amino]-2-(phenylmethoxycarbonylamino)butanoyl]piperidine-2-carboxylic acid | 1499188-20-3

• 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: (2S)-1-[(2R,3R)-3-[[(2S)-1-[2-[[2-[[(2S)-1-[(2R,3R)-3-[[(2S)-1-[2-[(2-aminoacetyl)-methylamino]acetyl]piperidine-2-carbonyl]amino]-2-(phenylmethoxycarbonylamino)butanoyl]piperidine-2-carbonyl]amino]acetyl]-methylamino]acetyl]piperidine-2-carbonyl]amino]-2-(phenylmethoxycarbonylamino)butanoyl]piperidine-2-carboxylic acid
• CAS: 1499188-20-3
• 化学式: C₅₈H₈₂N₁₂O₁₅
• 分子量: 1187.36
• InChiKey: MWDGCLKNFJQUPT-INVHTFHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  85
• 可旋转键数：
  25
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  349
• 氢给体数：
  7
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  (2S)-1-[(2R,3R)-3-[[(2S)-1-[2-[[2-[[(2S)-1-[(2R,3R)-3-[[(2S)-1-[2-[(2-aminoacetyl)-methylamino]acetyl]piperidine-2-carbonyl]amino]-2-(phenylmethoxycarbonylamino)butanoyl]piperidine-2-carbonyl]amino]acetyl]-methylamino]acetyl]piperidine-2-carbonyl]amino]-2-(phenylmethoxycarbonylamino)butanoyl]piperidine-2-carboxylic acid 在 叠氮磷酸二苯酯 、 10% palladium hydroxide on charcoal 、 氢气 、 碳酸氢钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 162.0h， 生成 N-[(3R,4R,7S,20S,27R,28R,31S,44S)-4,15,28,39-tetramethyl-2,6,13,16,19,26,30,37,40,43-decaoxo-27-(quinoline-2-carbonylamino)-1,5,12,15,18,25,29,36,39,42-decazapentacyclo[42.4.0.07,12.020,25.031,36]octatetracontan-3-yl]quinoline-2-carboxamide
  参考文献：
  名称：

  Total Synthesis of Quinaldopeptin and Its Analogues

  摘要：

  The first total synthesis of quinaldopeptin (1) was accomplished. Our approach to the synthesis of 1 includes the solid-phase peptide synthesis of the linear decapeptide 4 followed by macrocyclization and introduction of the quinoline chromophores 2 at a late stage of the synthesis. As for the preparation of 4, a fragment coupling approach was applied considering the C2 symmetrical structure of 1. Chromophore analogues 22 and 23 and desmethyl analogue 27 were also prepared in a manner similar to the synthesis of 1. Synthetic 1 exhibits a strong cytotoxicity with the IC50 value of 3.2 nM. On the other hand, the activity of 23 and 27 was largely reduced.

  DOI：

  10.1021/jo402267r
• 作为产物：
  描述：

  N-((((9H-fluoren-9-yl)methoxy)carbonyl)glycyl)-N-methylglycine 、 (2S)-1-[(2R,3R)-3-[[(2S)-1-[2-[[2-(9H-fluoren-9-ylmethoxycarbonylamino)acetyl]-methylamino]acetyl]piperidine-2-carbonyl]amino]-2-(phenylmethoxycarbonylamino)butanoyl]piperidine-2-carboxylic acid 、 Fmoc-Dab(Cbz)-L-Pip-OH 、 (2R)-1-[(9H-芴-9-甲氧基)羰基]哌啶-2-甲酸 在 2-chlorotrityl chloride polystyrene resin 、 N,N-二异丙基乙胺 、 哌啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S)-1-[(2R,3R)-3-[[(2S)-1-[2-[[2-[[(2S)-1-[(2R,3R)-3-[[(2S)-1-[2-[(2-aminoacetyl)-methylamino]acetyl]piperidine-2-carbonyl]amino]-2-(phenylmethoxycarbonylamino)butanoyl]piperidine-2-carbonyl]amino]acetyl]-methylamino]acetyl]piperidine-2-carbonyl]amino]-2-(phenylmethoxycarbonylamino)butanoyl]piperidine-2-carboxylic acid
  参考文献：
  名称：

  Total Synthesis of Quinaldopeptin and Its Analogues

  摘要：

  The first total synthesis of quinaldopeptin (1) was accomplished. Our approach to the synthesis of 1 includes the solid-phase peptide synthesis of the linear decapeptide 4 followed by macrocyclization and introduction of the quinoline chromophores 2 at a late stage of the synthesis. As for the preparation of 4, a fragment coupling approach was applied considering the C2 symmetrical structure of 1. Chromophore analogues 22 and 23 and desmethyl analogue 27 were also prepared in a manner similar to the synthesis of 1. Synthetic 1 exhibits a strong cytotoxicity with the IC50 value of 3.2 nM. On the other hand, the activity of 23 and 27 was largely reduced.

  DOI：

  10.1021/jo402267r