Fmoc-Dab(Cbz)-L-Pip-OH | 1499188-23-6

• 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: Fmoc-Dab(Cbz)-L-Pip-OH
• 英文别名: (2S)-1-[(2R,3R)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-2-(phenylmethoxycarbonylamino)butanoyl]piperidine-2-carboxylic acid
• CAS: 1499188-23-6
• 化学式: C₃₃H₃₅N₃O₇
• 分子量: 585.657
• InChiKey: POWWOLOTUGNBKJ-SPTGULJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  43
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-((((9H-fluoren-9-yl)methoxy)carbonyl)glycyl)-N-methylglycine 、 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-(9H-fluoren-9-ylmethoxycarbonylamino)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
• 作为产物：
  描述：

  N-Boc-L-哌啶-2-羧酸 在 吗啉 、 盐酸 、 四(三苯基膦)钯 、 caesium carbonate 、 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 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 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

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.