5'-O-(dimethoxytrityl)-4-N-benzoyl-2'-deoxy-L-cytidine | 141771-76-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5'-O-(dimethoxytrityl)-4-N-benzoyl-2'-deoxy-L-cytidine
• 英文别名: N-[1-[(2S,4R,5S)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide
• CAS: 141771-76-8
• 化学式: C₃₇H₃₅N₃O₇
• 分子量: 633.701
• InChiKey: MYSNCIZBPUPZMQ-AXIPTUPBSA-N

物化性质

• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  47
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5'-O-(dimethoxytrityl)-4-N-benzoyl-2'-deoxy-L-cytidine 在 2,6-二甲基吡啶 、 四氮唑 、 ammonium hydroxide 、 碘 、 三氯乙酸 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 12.75h， 生成 2'-deoxy-L-cytidine-3'-phosphate
  参考文献：
  名称：

  The Synthesis of 2′-Deoxy-L-Cytidine-3′-Phosphate

  摘要：

  Improvements in the synthesis of 2'-deoxy-L-cytidine-3'-phosphate from L-arabinose are described.

  DOI：

  10.1080/07328319808004314
• 作为产物：
  描述：

  4-氨基-1-(2-脱氧-beta-L-赤式-呋喃戊糖基)-2(1H)-嘧啶酮 在 吡啶 、 4-二甲氨基吡啶 作用下， 生成 5'-O-(dimethoxytrityl)-4-N-benzoyl-2'-deoxy-L-cytidine
  参考文献：
  名称：

  Enantio- and meso-DNAs: preparation, characterization, and interaction with complementary nucleic acids

  摘要：

  Enantio-DNAs (DNA having 2-deoxy-L-erythro-pentose, the enantiomer of natural 2-deoxy-D-ribose, as the sugar backbone) and meso-DNAs (DNA having an alternating sequence of L-sugars and D-sugars) were prepared by the use of an automated DNA synthesizer. The characteristics of the products were analyzed, focusing on enantio- and meso-dodecadeoxyadenylic acids (designated as L-dA12 and LD-dA12, respectively). Both L-dA12 and LD-dA12 were resistant to the action of phosphodiesterases, though LD-dA12 was decomposed very slowly by snake venom phosphodiesterase. The affinity of these dodecamers for their complementary natural nucleic acids, poly(U) and poly(dT), was analyzed by the UV-mixing curve and melting-temperature measurement methods. Both L-dA12 and LD-dA12 showed affinity for their complementary nucleic acids. L-dA12 showed high selectivity for poly(U) over poly(dT), and a UV-mixing curve analysis suggested that the interaction mode was triplex formation. LD-dA12 showed moderate selectivity for poly(U) over poly(dT). L-dT12, the counterpart of L-dA12, did not show any detectable interaction with its complementary natural nucleic acid.

  DOI：

  10.1021/ja00075a002

文献信息

• Synthesis and anti-HIV-1 integrase activity of modified dinucleotides
  作者：Yves Aubert、Marcel Chassignol、Victoria Roig、Gladys Mbemba、Julien Weiss、Hervé Meudal、Jean-François Mouscadet、Ulysse Asseline

  DOI：10.1016/j.ejmech.2009.09.007

  日期：2009.12

  The synthesis of a series of thirty-eight new modified dinucleotides and dinucleotide conjugate analogues of d-5′ApC3′ is described. The inhibitory activity of these compounds toward HIV-1 integrase was examined in enzymatic assays using the natural dinucleotide as a reference. Among the compounds, a perylene-dinucleotide conjugate has shown a two micromolar anti-integrase activity due to the presence

  一系列38新型改性二核苷酸和D-的二核苷酸偶联物类似物的合成5' APC 3'进行说明。这些酶对HIV-1整合酶的抑制活性在酶法测定中以天然二核苷酸为参考进行了检测。在这些化合物中，由于嵌入剂和二核苷酸的存在，a-二核苷酸缀合物具有两个微摩尔的抗整合酶活性。
• Enantio- and meso-DNAs: preparation, characterization, and interaction with complementary nucleic acids
  作者：Yuichi Hashimoto、Naoko Iwanami、Shizuyoshi Fujimori、Koichi Shudo

  DOI：10.1021/ja00075a002

  日期：1993.11

  Enantio-DNAs (DNA having 2-deoxy-L-erythro-pentose, the enantiomer of natural 2-deoxy-D-ribose, as the sugar backbone) and meso-DNAs (DNA having an alternating sequence of L-sugars and D-sugars) were prepared by the use of an automated DNA synthesizer. The characteristics of the products were analyzed, focusing on enantio- and meso-dodecadeoxyadenylic acids (designated as L-dA12 and LD-dA12, respectively). Both L-dA12 and LD-dA12 were resistant to the action of phosphodiesterases, though LD-dA12 was decomposed very slowly by snake venom phosphodiesterase. The affinity of these dodecamers for their complementary natural nucleic acids, poly(U) and poly(dT), was analyzed by the UV-mixing curve and melting-temperature measurement methods. Both L-dA12 and LD-dA12 showed affinity for their complementary nucleic acids. L-dA12 showed high selectivity for poly(U) over poly(dT), and a UV-mixing curve analysis suggested that the interaction mode was triplex formation. LD-dA12 showed moderate selectivity for poly(U) over poly(dT). L-dT12, the counterpart of L-dA12, did not show any detectable interaction with its complementary natural nucleic acid.
• The Synthesis of 2′-Deoxy-L-Cytidine-3′-Phosphate
  作者：Igor A. Kozlov、Leslie E. Orgel

  DOI：10.1080/07328319808004314

  日期：1998.12

  Improvements in the synthesis of 2'-deoxy-L-cytidine-3'-phosphate from L-arabinose are described.