(2R,4R)-2-carboxymethoxymethyl-4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (2R,4R)-2-carboxymethoxymethyl-4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester
• 英文别名: 2-[[(2R,4R)-1-(9H-fluoren-9-ylmethoxycarbonyl)-4-(5-methyl-2,4-dioxopyrimidin-1-yl)pyrrolidin-2-yl]methoxy]acetic acid
• 化学式: C₂₇H₂₇N₃O₇
• 分子量: 505.527
• InChiKey: BABRKJDXMZQMNB-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-3-benzoylthymine 在 sodium hydroxide 、 sodium carbonate 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.25h， 生成 (2R,4R)-2-carboxymethoxymethyl-4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester
  参考文献：
  名称：

  掺入吡咯烷衍生的核氨基酸的聚酰胺基核酸类似物的合成和杂交性质。

  摘要：

  已经合成了Ndelta-Fmoc保护的I型核苷酸（碱基= T，C，A），并用作构建新型聚酰胺基核酸类似物的基础。同嘧啶低聚物A以明显的亲和力和序列特异性方式结合互补RNA，而未观察到与互补DNA的结合。

  DOI：

  10.1016/s0960-894x(00)00121-9

文献信息

• Synthesis of pyrrolidine-based oxy-peptide nucleic acids carrying four types of nucleobases and their transport into cytoplasm
  作者：Mizuki Kitamatsu、Akiko Takahashi、Takashi Ohtsuki、Masahiko Sisido

  DOI：10.1016/j.tet.2010.10.056

  日期：2010.12

  We synthesized 16 pyrrolidine-based oxy-peptide nucleic acid (POPNA) monomers carrying four different nucleobases onto four different stereoisomers of pyrrolidine rings. Using these monomers, we prepared POPNA oligomers, which formed sequence-specific hybrids with DNAs. The oligomer configurations influenced the hybrid stability. The oligomers were not taken into CHO cells. However, they could enter the cell cytoplasm when mixed with the influenza virus hemagglutinin peptide-arginine heptamer conjugate. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and hybridization properties of polyamide based nucleic acid analogues incorporating pyrrolidine-derived nucleoamino acids
  作者：Karl-Heinz Altmann、Dieter Hüsken、Bernard Cuenoud、Carlos Garcı́a-Echeverrı́a

  DOI：10.1016/s0960-894x(00)00121-9

  日期：2000.5

  Ndelta-Fmoc protected nucleoamino acids of type I (Base = T, C, A) have been synthesized and employed as building blocks for the construction of novel polyamide based nucleic acid analogues. Homopyrimidine oligomer A binds to complementary RNA with significant affinity and in a sequence-specific fashion, while no binding was observed to complementary DNA.

  已经合成了Ndelta-Fmoc保护的I型核苷酸（碱基= T，C，A），并用作构建新型聚酰胺基核酸类似物的基础。同嘧啶低聚物A以明显的亲和力和序列特异性方式结合互补RNA，而未观察到与互补DNA的结合。