Boc-Asp-Pro-D-Val-Phe | 1289154-08-0

• 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: Boc-Asp-Pro-D-Val-Phe
• CAS: 1289154-08-0
• 化学式: C₂₉H₄₂N₄O₉
• 分子量: 590.674
• InChiKey: LNTHCISFPXWBMF-VVSUKSJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  42.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  180.44
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  甲醇 、 BOC-L-天门冬氨酸Β-9-芴甲氧羰酰甲酯 、 Fmoc-L-脯氨酸 、 Fmoc-L-苯丙氨酸 、 Fmoc-D-缬氨酸 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 生成 Boc-Asp-Pro-D-Val-Phe
  参考文献：
  名称：

  One-Bead-One-Catalyst Approach to Aspartic Acid-Based Oxidation Catalyst Discovery

  摘要：

  We report an approach to the high-throughput screening of asymmetric oxidation catalysts The strategy is based on application of the one library approach, wherein each of our catalyst candidates is based on a peptide scaffold. For this purpose, we rely on a recently developed catalytic cycle that employs an acid-peracid shuttle. To implement our approach, we developed a compatible linker and demonstrated that the library format is amenable to screening and sequencing of catalysts employing partial Edman degradation and, MALDI mass spectrometry analysis. The system was applied to the discovery (and rediscovery) of catalysts for the enantioselective oxidation of a cyclohexene derivative. The system is now poised for application to unprecedented substrate classes for asymmetric oxidation reactions.

  DOI：

  10.1021/co200010v
• 作为试剂：
  描述：

  cyclohex-1-en-1-ylmethyl phenylcarbamate 在 4-二甲氨基吡啶 、 Boc-Asp-Pro-D-Val-Phe 、 双氧水 、 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 生成 [(1R,6R)-7-oxabicyclo[4.1.0]heptan-1-yl]methyl N-phenylcarbamate 、 (1S,6S)-7-oxabicyclo[4.1.0]heptan-1-yl phenylcarbamate
  参考文献：
  名称：

  One-Bead-One-Catalyst Approach to Aspartic Acid-Based Oxidation Catalyst Discovery

  摘要：

  We report an approach to the high-throughput screening of asymmetric oxidation catalysts The strategy is based on application of the one library approach, wherein each of our catalyst candidates is based on a peptide scaffold. For this purpose, we rely on a recently developed catalytic cycle that employs an acid-peracid shuttle. To implement our approach, we developed a compatible linker and demonstrated that the library format is amenable to screening and sequencing of catalysts employing partial Edman degradation and, MALDI mass spectrometry analysis. The system was applied to the discovery (and rediscovery) of catalysts for the enantioselective oxidation of a cyclohexene derivative. The system is now poised for application to unprecedented substrate classes for asymmetric oxidation reactions.

  DOI：

  10.1021/co200010v