methyl N2-{[(benzyloxy)carbonyl]-L-aspart-1-yl}-(2S,3R,4R)-3-{[(tert-butoxy)carbonyl]amino}-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)prolinate | 269730-21-4

• 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: methyl N2-{[(benzyloxy)carbonyl]-L-aspart-1-yl}-(2S,3R,4R)-3-{[(tert-butoxy)carbonyl]amino}-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)prolinate
• 英文别名: methyl N²-{[(benzyloxy)carbonyl]-L-aspart-1-yl}-(2S,3R,4R)-3-{[(tert-butoxy)carbonyl]amino}-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)prolinate
• CAS: 269730-21-4
• 化学式: C₃₅H₄₂N₄O₁₁
• 分子量: 694.739
• InChiKey: SNTZPZUSODBCOI-NAUAGNGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  50.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  186.95
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl N2-{[(benzyloxy)carbonyl]-L-aspart-1-yl}-(2S,3R,4R)-3-{[(tert-butoxy)carbonyl]amino}-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)prolinate 在 palladium on activated charcoal 氢气 、 甲基肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 121.0h， 生成 ((3S,7R,8R,8aS)-7-Amino-8-tert-butoxycarbonylamino-1,4-dioxo-octahydro-pyrrolo[1,2-a]pyrazin-3-yl)-acetic acid tert-butyl ester
  参考文献：
  名称：

  利用衍生自(2S,3R,4R)-二氨基脯氨酸的模板合成和溶液构象β-发夹模拟物

  摘要：

  A novel template was synthesized for stabilizing beta-hairpin conformations in cyclic peptide mimetics. The template is a diketopiperazine derived formally from L-aspartic acid and (2S,3R,4R)-diaminoproline, the latter being available by an efficient synthetic route from vitamin C, The template was incorporated by solid-phase peptide synthesis into a cyclic loop mimetic containing the sequence (-Ala-Asn-Pro-Asn-Ala-Ala-template-). This mimetic was shown by NMR to adopt a stable beta-hairpin conformation in (D-8)DMSO solution. The template may prove to be: generally useful for creating small-molecule mimetics: of hairpin loops on proteins of diverse function.

  DOI：

  10.1002/(sici)1522-2675(20000216)83:2<444::aid-hlca444>3.0.co;2-r
• 作为产物：
  描述：

  2-benzyl 6-(tert-butyl) (1S,4R,5R)-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-7-oxo-2,6-diazabicyclo[3.2.0]heptane-2,6-dicarboxylate 在 palladium on activated charcoal N-羟基-7-氮杂苯并三氮唑 、 水 、 氢气 、 sodium 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 、 乙醚 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 methyl N2-{[(benzyloxy)carbonyl]-L-aspart-1-yl}-(2S,3R,4R)-3-{[(tert-butoxy)carbonyl]amino}-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)prolinate
  参考文献：
  名称：

  利用衍生自(2S,3R,4R)-二氨基脯氨酸的模板合成和溶液构象β-发夹模拟物

  摘要：

  A novel template was synthesized for stabilizing beta-hairpin conformations in cyclic peptide mimetics. The template is a diketopiperazine derived formally from L-aspartic acid and (2S,3R,4R)-diaminoproline, the latter being available by an efficient synthetic route from vitamin C, The template was incorporated by solid-phase peptide synthesis into a cyclic loop mimetic containing the sequence (-Ala-Asn-Pro-Asn-Ala-Ala-template-). This mimetic was shown by NMR to adopt a stable beta-hairpin conformation in (D-8)DMSO solution. The template may prove to be: generally useful for creating small-molecule mimetics: of hairpin loops on proteins of diverse function.

  DOI：

  10.1002/(sici)1522-2675(20000216)83:2<444::aid-hlca444>3.0.co;2-r