4-[(tert-butoxycarbonyl)amino]-1-but-3-enylpyrrole-2-carboxylic acid | 530103-00-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-[(tert-butoxycarbonyl)amino]-1-but-3-enylpyrrole-2-carboxylic acid
• 英文别名: 1-but-3-enyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrole-2-carboxylic acid
• CAS: 530103-00-5
• 化学式: C₁₄H₂₀N₂O₄
• 分子量: 280.324
• InChiKey: QGOURJAAEHLIBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  80.56
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-叔丁氧羰氨基-1-甲基-1H-吡咯-2-苯并噻唑羧酸甲酯 、 N,N-二甲基-1,3-二氨基丙烷 、 1-Methyl-1H-imidazole-2-carboxylic acid benzotriazol-1-yl ester 、 4-[(tert-butoxycarbonyl)amino]-1-but-3-enylpyrrole-2-carboxylic acid 、 alkaline earth salt of/the/ methylsulfuric acid 生成
  参考文献：
  名称：

  Parallel Synthesis of H-pin Polyamides by Alkene Metathesis on Solid Phase

  摘要：

  A small library of H-pin polyamides with variable aliphatic bridge lengths (CH2)(n), where n = 4-8, connecting a central Py/Py pair was prepared via parallel synthesis with Ru-catalyzed alkene metathesis on solid phase as a complexity-generating cross-linking reaction. DNA binding affinities and sequence specificities were analyzed for each member of the library to determine the optimum linker length. An H-pin polyamide with a six-methylene bridge was found to have the highest affinity to its match site with high selectivity over a 1-bp mismatch site, The relationship between the number of methylenes in the linker (CH2)n and affinity is n = 6 > 4 > 7 > 5 > 8. These results indicate that 6 followed by 4 methylene-bridged polyamides represent the optimum spacer length for the H-pin motif in the DNA minor groove. Importantly, the H-pin is competitive with hairpin polyamides with respect to affinity and specificity. The metathesis-based convergent synthetic route to H-pin polyamides expands the scope of readily available DNA recognition motifs for small molecule-based gene regulation studies.

  DOI：

  10.1021/ja0213221
• 作为产物：
  描述：

  1-But-3-enyl-4-tert-butoxycarbonylamino-1H-pyrrole-2-carboxylic acid 2-trimethylsilanyl-ethyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到4-[(tert-butoxycarbonyl)amino]-1-but-3-enylpyrrole-2-carboxylic acid
  参考文献：
  名称：

  Parallel Synthesis of H-pin Polyamides by Alkene Metathesis on Solid Phase

  摘要：

  A small library of H-pin polyamides with variable aliphatic bridge lengths (CH2)(n), where n = 4-8, connecting a central Py/Py pair was prepared via parallel synthesis with Ru-catalyzed alkene metathesis on solid phase as a complexity-generating cross-linking reaction. DNA binding affinities and sequence specificities were analyzed for each member of the library to determine the optimum linker length. An H-pin polyamide with a six-methylene bridge was found to have the highest affinity to its match site with high selectivity over a 1-bp mismatch site, The relationship between the number of methylenes in the linker (CH2)n and affinity is n = 6 > 4 > 7 > 5 > 8. These results indicate that 6 followed by 4 methylene-bridged polyamides represent the optimum spacer length for the H-pin motif in the DNA minor groove. Importantly, the H-pin is competitive with hairpin polyamides with respect to affinity and specificity. The metathesis-based convergent synthetic route to H-pin polyamides expands the scope of readily available DNA recognition motifs for small molecule-based gene regulation studies.

  DOI：

  10.1021/ja0213221