(2R,3R)-3-[(9-fluorenylmethoxycarbonyl)amino]-2-[(benzyloxycarbonyl)amino]butanoic acid | 1499188-28-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (2R,3R)-3-[(9-fluorenylmethoxycarbonyl)amino]-2-[(benzyloxycarbonyl)amino]butanoic acid
• 英文别名: (2R,3R)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-2-(phenylmethoxycarbonylamino)butanoic acid
• CAS: 1499188-28-1
• 化学式: C₂₇H₂₆N₂O₆
• 分子量: 474.513
• InChiKey: ZPKVLJSESKDMQU-MZNJEOGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-[(9-fluorenylmethoxycarbonyl)amino]-2-[(benzyloxycarbonyl)amino]butanoic acid 、 allyl L-pipecolate hydrochloride 在 吗啉 、 四(三苯基膦)钯 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 Fmoc-Dab(Cbz)-L-Pip-OH
  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：

  tert-butyl (2R,3R)-2-tert-butyloxycarbonylamino-3-(9-fluorenylmethyloxycarbonylamino)butyrate 在 碳酸氢钠 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 生成 (2R,3R)-3-[(9-fluorenylmethoxycarbonyl)amino]-2-[(benzyloxycarbonyl)amino]butanoic 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

文献信息

• Total Synthesis of Quinaldopeptin and Its Analogues
  作者：Satoshi Ichikawa、Takuya Okamura、Akira Matsuda

  DOI：10.1021/jo402267r

  日期：2013.12.20

  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.