5'-O-phosphoryl-2'-deoxycytidylyl-(3'->5')-1'-deoxy-2'-isouridine | 356518-61-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: 5'-O-phosphoryl-2'-deoxycytidylyl-(3'->5')-1'-deoxy-2'-isouridine
• 英文别名: pdCpIsodU；[(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-2-(phosphonooxymethyl)oxolan-3-yl] [(2R,3S,4R)-4-(2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl hydrogen phosphate
• CAS: 356518-61-1
• 化学式: C₁₈H₂₅N₅O₁₄P₂
• 分子量: 597.369
• InChiKey: WGIAJLAXTLAWOI-LWHUEDLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.7
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  269
• 氢给体数：
  6
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  1,4-anhydro-2-deoxy-2-<3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl>-D-arabinitol 在 吡啶 、 二氯乙酸 、 ammonium hydroxide 、 TPS-TAZ 、 溶剂黄146 、 2-O-(4,4'-dimethoxytrityl) sulfonyldiethanol disodium phosphate 作用下， 以 二氯甲烷 为溶剂， 生成 5'-O-phosphoryl-2'-deoxycytidylyl-(3'->5')-1'-deoxy-2'-isouridine
  参考文献：
  名称：

  Discovery of a nuclease-resistant, non-natural dinucleotide that inhibits HIV-1 integrase

  摘要：

  Integration of HIV viral DNA into human chromosomal DNA catalyzed by HIV integrase is essential for the replication of HIV. Discovery of novel inhibitors of HIV integrase is of considerable significance in approaches to the development of therapeutic agents against AIDS. We have synthesized a new dinucleotide 1 with an internucleotide phosphate bond that is unusually resistant to exonucleases. This compound exhibits potent anti-HIV-1 integrase activity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00231-1

文献信息

• A NEW PROCEDURE FOR THE PHOSPHORYLATION OF NUCLEOSIDES: APPLICATION TO THE DISCOVERY OF INHIBITORS OF HIV INTEGRASE
  作者：Vasu Nair、Michael Taktakishvili

  DOI：10.1081/ncn-100002419

  日期：2001.3.31

  A new phosphorylating agent for nucleosides, 2-O-(4,4′-dimethoxytrityl) ethylsulfonylethan-2′-yl-phosphate (1), has been developed by us. In the many examples studied by us, phosphorylation yields were found to be very high (about 90%). The procedure appears to be remarkably general and can be utilized for the phosphorylation of many biomolecules. Successful application of this phosphorylation method

  我们已经开发出一种新的核苷磷酸化剂2-O-（4,4'-二甲氧基三苯甲基）乙基磺酰lethan-2'-基磷酸酯（1）。在我们研究的许多实例中，发现磷酸化的收率非常高（约90％）。该程序似乎非常通用，可用于许多生物分子的磷酸化。这种磷酸化方法的成功应用有助于在我们的实验室中发现HIV整合酶的抑制剂。