α-L-aspartyl β-benzyl ester L-aspartic acid dimethyl ester | 871927-90-1

• 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: α-L-aspartyl β-benzyl ester L-aspartic acid dimethyl ester
• CAS: 871927-90-1
• 化学式: C₁₇H₂₂N₂O₇
• 分子量: 366.371
• InChiKey: YQSHBYMRHFHVOP-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.33
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  134.02
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  α-L-aspartyl β-benzyl ester L-aspartic acid dimethyl ester 在 palladium on activated charcoal N-甲基吗啉 、 盐酸 、 sodium hydroxide 、 氢气 、 氯甲酸乙酯 、 乙酸乙酯 、 silver(l) oxide 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 生成 2-[(2S,5S)-5-(Benzylcarbamoyl-methyl)-1,4-bis-hexylcarbamoylmethyl-3,6-dioxo-piperazin-2-yl]-N-tert-butyl-acetamide
  参考文献：
  名称：

  A new diketopiperazine tetra-carboxylic acid as template for the homogeneous phase synthesis of chemical libraries

  摘要：

  The synthesis of a tetra-functionalized template based on a diketopiperazine skeleton is described together with some protocols for the synthesis of families of diversomers using a parallel synthesis approach. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00961-1
• 作为产物：
  描述：

  Boc-L-天冬氨酸 4-苄酯 在 N-甲基吗啉 、 盐酸 、 Amberlite IRA-400 、 乙酸乙酯 、 氯甲酸异丁酯 作用下， 生成 α-L-aspartyl β-benzyl ester L-aspartic acid dimethyl ester
  参考文献：
  名称：

  A new diketopiperazine tetra-carboxylic acid as template for the homogeneous phase synthesis of chemical libraries

  摘要：

  The synthesis of a tetra-functionalized template based on a diketopiperazine skeleton is described together with some protocols for the synthesis of families of diversomers using a parallel synthesis approach. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00961-1

文献信息

• Synthesis and Protein Degradation Capacity of Photoactivated Enediynes
  作者：Farid S. Fouad、Justin M. Wright、Gary Plourde II,、Ajay D. Purohit、Justin K. Wyatt、Ahmed El-Shafey、George Hynd、Curtis F. Crasto、Yiqing Lin、Graham B. Jones

  DOI：10.1021/jo051403q

  日期：2005.11.1

  The viability of proteins as targets of thermally and photoactivated enediynes has been confirmed at the molecular level. Model studies using a labeled substrate confirmed the efficacy of atom transfer from diyl radicals produced from enediynes to form captodatively stabilized carbon centered aminoacyl radicals, which then undergo either fragmentation or dimerization. To exploit this finding, a family of enediynes was developed using an intramolecular coupling strategy. Derivatives were prepared and used to target specific proteins, showing good correlation between affinity and photoinduced protein degrading activity. The findings have potential applications in the design of artificial chemical proteases and add to our understanding of the mechanism of action of the clinically important enediyne antitumor antibiotics.