1,6-di-[4-[(tert-butoxycarbonyl)amino]-2-carboxy-N-pyrrolyl]hexane | 530103-08-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1,6-di-[4-[(tert-butoxycarbonyl)amino]-2-carboxy-N-pyrrolyl]hexane
• CAS: 530103-08-3
• 化学式: C₂₆H₃₈N₄O₈
• 分子量: 534.61
• InChiKey: NWMBDKVIMCKLCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  38.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  161.12
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-羟基苯并三唑 、 1,6-di-[4-[(tert-butoxycarbonyl)amino]-2-carboxy-N-pyrrolyl]hexane 在 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以79%的产率得到1,6-di-[4-[(tert-butoxycarbonyl)amino]-2-[[(1-benzotriazolyl)oxy]carbonyl]-N-pyrrolyl]hexane
  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：

  (2-trimethylsilyl)-ethyl 4-nitropyrrole-2-carboxylate 在 palladium on activated charcoal 、 Grubbs catalyst first generation 四丁基氟化铵 、 氢气 、 四丁基碘化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 丙酮 为溶剂， 20.0 ℃ 、2.76 MPa 条件下， 反应 84.0h， 生成 1,6-di-[4-[(tert-butoxycarbonyl)amino]-2-carboxy-N-pyrrolyl]hexane
  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