3-[(2S,4S)-2-(tert-butyloxycarbonylaminomethyl)-4-(thymin-1-yl)-pyrrolidin-1-yl]-propanoic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-[(2S,4S)-2-(tert-butyloxycarbonylaminomethyl)-4-(thymin-1-yl)-pyrrolidin-1-yl]-propanoic acid
• 英文别名: [(2S,4S)-2-(tert-butoxycarbonylaminomethyl)-4-(thymin-1-yl)-pyrrolidin-1-yl]-propanoic acid；3-[(2S,4S)-4-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidin-1-yl]propanoic acid
• 化学式: C₁₈H₂₈N₄O₆
• 分子量: 396.444
• InChiKey: HUJYRSSBPUDSNF-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  128
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  L-羟基脯氨酸 在 palladium on activated charcoal 、 镍 吡啶 、 sodium hydroxide 、 sodium tetrahydroborate 、 氯化亚砜 、 sodium azide 、 氢气 、 碳酸氢钠 、 三乙胺 、 三苯基膦 、 lithium chloride 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 20.0~55.0 ℃ 、413.68 kPa 条件下， 反应 64.5h， 生成 3-[(2S,4S)-2-(tert-butyloxycarbonylaminomethyl)-4-(thymin-1-yl)-pyrrolidin-1-yl]-propanoic acid
  参考文献：
  名称：

  Backbone extended pyrrolidine PNA (bepPNA): a chiral PNA for selective RNA recognition

  摘要：

  Synthesis of cationic, chiral PNA analogues with an extra atom in the backbone (bepPNA) is reported. The (2S,4S) geometry of the pyrrolidine ring, and an additional carbon atom in the backbone of homopyrimidine-bepPNAs resulted in the optimization of the inter-nucleobase distance, such that selective binding to complementary RNA over DNA was observed in the triplex mode. It was evident from circular dichroism studies that oligomers with mixed aminoethylglycyl-bep (aeg-bep) repeating units, and also bepPNA with homogeneous backbone attained structures quite different from those of aegPNA(2):RNA/DNA complexes. The bepPNA. when incorporated in a duplex forming mixed purine-pyrimidine sequence, also showed a preference for binding complementary RNA over DNA. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.002

文献信息

• Backbone-extended pyrrolidine peptide nucleic acids (bepPNA): design, synthesis and DNA/RNA binding studies
  作者：T. Govindaraju、Vaijayanti A. Kumar

  DOI：10.1039/b413542c

  日期：——

  One-carbon extended conformationally constrained pyrrolidine PNA monomer (bepPNA) has been synthesized, incorporated into PNA sequences at predefined positions, and showed selective RNA binding properties.

  一碳扩展构象约束的吡咯烷PNA单体（bepPNA）已被合成，并在预定位置掺入PNA序列，并显示出选择性的RNA结合特性。
• Backbone extended pyrrolidine PNA (bepPNA): a chiral PNA for selective RNA recognition
  作者：T. Govindaraju、Vaijayanti A. Kumar

  DOI：10.1016/j.tet.2005.12.002

  日期：2006.3

  Synthesis of cationic, chiral PNA analogues with an extra atom in the backbone (bepPNA) is reported. The (2S,4S) geometry of the pyrrolidine ring, and an additional carbon atom in the backbone of homopyrimidine-bepPNAs resulted in the optimization of the inter-nucleobase distance, such that selective binding to complementary RNA over DNA was observed in the triplex mode. It was evident from circular dichroism studies that oligomers with mixed aminoethylglycyl-bep (aeg-bep) repeating units, and also bepPNA with homogeneous backbone attained structures quite different from those of aegPNA(2):RNA/DNA complexes. The bepPNA. when incorporated in a duplex forming mixed purine-pyrimidine sequence, also showed a preference for binding complementary RNA over DNA. (c) 2005 Elsevier Ltd. All rights reserved.