2'-deoxycytidylyl-(3',5')-thymidine phosphate | 4829-64-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - （3'->5'）-二核苷酸和类似物
• 英文名称: 2'-deoxycytidylyl-(3',5')-thymidine phosphate
• 英文别名: d；d[CpT]；Deoxycytidylthymidin；Deoxycytidylylthymidin-monophosphat；2'-deoxy-cytidylyl-(3'->5')-thymidine；dC-dT；[(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-2-(hydroxymethyl)oxolan-3-yl] [(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl hydrogen phosphate
• CAS: 4829-64-5
• 化学式: C₁₉H₂₆N₅O₁₁P
• 分子量: 531.416
• InChiKey: OUJLZFGNZMPALU-SWTKMSQOSA-N

物化性质

• 密度：
  1.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  223
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  胸苷3'-苯甲酸酯 在 N-甲基咪唑 、 1,2,4-Triisopropyl-benzol-sulfonsaeure-(5)-chlorid 、 氨 、 溶剂黄146 作用下， 以 吡啶 为溶剂， 反应 20.5h， 生成 2'-deoxycytidylyl-(3',5')-thymidine phosphate
  参考文献：
  名称：

  Synthesis of oligonucleotides containing 3?-terminal nucleotides with inverted configurations of the sugar residues

  摘要：

  DOI：

  10.1007/bf00600838

文献信息

• O-Selectivity and Utility of Phosphorylation Mediated by Phosphite Triester Intermediates in the N-Unprotected Phosphoramidite Method
  作者：Akihiro Ohkubo、Yusuke Ezawa、Kohji Seio、Mitsuo Sekine

  DOI：10.1021/ja048125h

  日期：2004.9.1

  molecular orbital interactions between the reactive intermediates and the nucleophiles such as the amino or hydroxyl groups of nucleosides. Furthermore, longer oligonucleotides were synthesized not only by a manual operation but also by a DNA synthesizer. The utility of our new method was demonstrated by the successful synthesis of a base-labile modified oligodeoxyribonucleotide having 4-N-acetyldeoxycytidine

  以前，由于 dA 和 dC 的氨基对三价磷 (III) 型亚磷酸化试剂具有高反应性，因此无法在 N-未保护的亚磷酰胺方法中进行聚合物载体上的 O 选择性磷酸化。在本文中，我们开发了一种名为“活化亚磷酸酯方法”的新偶联策略，其中亚磷酸三酯中间体 1 介导了亚磷酸化。将 1-羟基苯并三唑作为促进剂应用于固相合成导致了优异的 O-选择性超过 99.7%。这种 O 选择性可以通过反应中间体和亲核试剂（如核苷的氨基或羟基）之间的前沿分子轨道相互作用来解释。此外，更长的寡核苷酸不仅可以通过手动操作合成，也可以通过 DNA 合成仪合成。通过成功合成具有 4-N-乙酰脱氧胞苷残基的碱不稳定修饰寡脱氧核糖核苷酸，证明了我们新方法的实用性。最后，通过使用 6-三氟甲基-1-羟基苯并三唑和苯并咪唑鎓三氟甲磺酸盐的组合试剂，可以以良好的产率合成含有 dA 或 dC 的 DNA 20 聚体。
• A new approach to the synthesis of phosphotriester intermediates of nucleosides and nucleic acids
  作者：G. van der Marel、C.A.A. van Boeckel、G. Wille、J.H. van Boom

  DOI：10.1016/s0040-4039(01)91336-x

  日期：1981.1

  Aryl phosphorodichloridates can be converted by means of 1-hydroxybenzotriazole into an effective phosphorylating agent, which can be applied to the synthesis of phosphotriester intermediates of nucleic acids.

  可以通过1-羟基苯并三唑将芳基二氯磷酸酯转化为有效的磷酸化剂，该试剂可以用于合成核酸的磷酸三酯中间体。
• N-pent-4-enoyl nucleosides: Application in the synthesis of support-bound and free oligonucleotide analogs by the H-phosphonate approach
  作者：Radhakrishnan P. Iyer、Theresa Devlin、Ivan Habus、Nan-Hui Ho、Dong Yu、Sudhir Agrawal

  DOI：10.1016/0040-4039(96)00066-4

  日期：1996.3

  N-pent-4-enoyl nucleoside H-phosphonates are versatile building blocks for the synthesis of support-bound and free oligonucleotide analogs.

  N-戊-4-烯酰基核苷H-膦酸酯是用于合成支持物结合的和游离的寡核苷酸类似物的通用结构单元。
• <i>O</i>-Selective Condensation Using P−N Bond Cleavage in RNA Synthesis without Base Protection
  作者：Akihiro Ohkubo、Yasukazu Kuwayama、Tomomi Kudo、Hirosuke Tsunoda、Kohji Seio、Mitsuo Sekine

  DOI：10.1021/ol800911b

  日期：2008.7.3

  In RNA synthesis without base protection, a new method for O-selective condensation with more than 99% selectivity was developed by 6-nitro-HOBt-mediated cleavage of undesired P(III)-N bonds on nucleobase moieties. Moreover, we for the first time succeeded in synthesizing oligoRNAs without base protection.
• A new strategy for the synthesis of oligodeoxynucleotides directed towards perfect O-selective internucleotidic bond formation without base protection
  作者：Akihiro Ohkubo、Kohji Seio、Mitsuo Sekine

  DOI：10.1016/j.tetlet.2003.10.156

  日期：2004.1

  Deoxyadenosine and deoxycytidine have nucleophilic amino groups so that the undesired N-phosphitylation of these amino groups occurred in the previous phosphoramidite methods without base protection. We report that the N-phosphitylation could be considerably suppressed in our new HOBt-mediated coupling strategy via phosphite intermediates as reactive species. Thus, 99.7-99.9% O-selective internucleotidic bond formation was achieved. (C) 2003 Published by Elsevier Ltd.