(2R,4S,5R)-2-(2-amino-4-oxo-3,4-dihydropyrimidin-5-yl)-4-hydroxy-5-hydroxymethyl pyrrolidine | 855519-64-1

• 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: (2R,4S,5R)-2-(2-amino-4-oxo-3,4-dihydropyrimidin-5-yl)-4-hydroxy-5-hydroxymethyl pyrrolidine
• 英文别名: 2-amino-5-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-1H-pyrimidin-6-one
• CAS: 855519-64-1
• 化学式: C₉H₁₄N₄O₃
• 分子量: 226.235
• InChiKey: BMELOMCXUWBQHI-QYNIQEEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  120
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,4S,5R)-2-(2-amino-4-oxo-3,4-dihydropyrimidin-5-yl)-4-hydroxy-5-hydroxymethyl pyrrolidine 在 吡啶 、 碳酸氢钠 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 7.0h， 生成 (2R,3S,5R)-5-(2-Amino-6-oxo-1,6-dihydro-pyrimidin-5-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxy]-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester
  参考文献：
  名称：

  Pyrrolidino-DNA

  摘要：

  We synthesized pyrrolidino-C-nucleosides, incorporated them into oligodeoxynucleotides and investigated their pairing properties. The thermal duplex and triplex stabilities were measured. While triplex formation is destabilized in the case of pyrrolidino-pseudo-U and -T, pyrrolidino-pseudo-iso-C leads to an increase of the T-m value for third strand dissociation. Duplexes Lire destabilized with all pyrrolidino-C-nucleosides.

  DOI：

  10.1081/ncn-120022832
• 作为产物：
  描述：

  (2R,5R)-5-(2-Benzoylamino-6-oxo-1,6-dihydro-pyrimidin-5-yl)-3-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 (2R,4S,5R)-2-(2-amino-4-oxo-3,4-dihydropyrimidin-5-yl)-4-hydroxy-5-hydroxymethyl pyrrolidine
  参考文献：
  名称：

  Pyrrolidino-DNA

  摘要：

  We synthesized pyrrolidino-C-nucleosides, incorporated them into oligodeoxynucleotides and investigated their pairing properties. The thermal duplex and triplex stabilities were measured. While triplex formation is destabilized in the case of pyrrolidino-pseudo-U and -T, pyrrolidino-pseudo-iso-C leads to an increase of the T-m value for third strand dissociation. Duplexes Lire destabilized with all pyrrolidino-C-nucleosides.

  DOI：

  10.1081/ncn-120022832

文献信息

• Synthesis and triplex forming properties of pyrrolidino pseudoisocytidine containing oligodeoxynucleotides
  作者：Alain Mayer、Adrian Häberli、Christian J. Leumann

  DOI：10.1039/b502799c

  日期：——

  Pyrrolidino pseudo-C-nucleosides are isosteres of natural deoxynucleosides which are protonated at the pyrrolidino ring nitrogen under physiological conditions. As constituents of a triplex forming oligodeoxynucleotide (TFO), the positive charge is expected to stabilise DNA triple helices via electrostatic interactions with the phosphodiester backbone of the target DNA. We describe the synthesis of the pyrrolidino isocytidine pseudonucleoside and the corresponding phosphoramidite building block and its incorporation into TFOs. Such TFOs show substantially increased DNA affinity compared to unmodified oligodeoxynucleotides. The increase in affinity is shown to be due to the positive charge at the pyrrolidino subunit.

  吡咯烷假C-核苷是天然脱氧核苷的电子等排体，其在生理条件下在吡咯烷环氮处质子化。作为形成三链体的寡脱氧核苷酸 (TFO) 的组成部分，正电荷有望通过与目标 DNA 的磷酸二酯主链的静电相互作用来稳定 DNA 三螺旋。我们描述了吡咯烷异胞苷假核苷和相应的亚磷酰胺结构单元的合成以及将其掺入 TFO 中。与未修饰的寡脱氧核苷酸相比，此类 TFO 显示出显着增加的 DNA 亲和力。亲和力的增加被证明是由于吡咯烷亚基上的正电荷。
• Pyrrolidino-DNA
  作者：Adrian Häberli、Alain Mayer、Christian J. Leumann

  DOI：10.1081/ncn-120022832

  日期：2003.10

  We synthesized pyrrolidino-C-nucleosides, incorporated them into oligodeoxynucleotides and investigated their pairing properties. The thermal duplex and triplex stabilities were measured. While triplex formation is destabilized in the case of pyrrolidino-pseudo-U and -T, pyrrolidino-pseudo-iso-C leads to an increase of the T-m value for third strand dissociation. Duplexes Lire destabilized with all pyrrolidino-C-nucleosides.