O^5'-(2,2-dimethyl-propionyl)-2'-deoxy-uridine | 57846-84-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: O^5'-(2,2-dimethyl-propionyl)-2'-deoxy-uridine
• 英文别名: ((2R,3S,5R)-5-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-hydroxytetrahydrofuran-2-yl)methyl Pivalate；[(2R,3S,5R)-5-(2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 57846-84-1
• 化学式: C₁₄H₂₀N₂O₆
• 分子量: 312.323
• InChiKey: INSKKFQSZLBVEW-IQJOONFLSA-N

物化性质

• 熔点：
  154-155 °C
• 密度：
  1.315±0.06 g/cm3(Predicted)
• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  O^5'-(2,2-dimethyl-propionyl)-2'-deoxy-uridine 在 palladium on activated charcoal 四氯化碳 、 potassium tert-butylate 、 氨 、 氢气 、 三苯基膦 作用下， 以 乙醇 、 氯仿 、 叔丁醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 52.0h， 生成 2,3-二脱氧胞啶
  参考文献：
  名称：

  Improved Synthesis of 2′,3′-Dideoxycytidine (d2C) and Its Correlated Nucleoside Analogues

  摘要：

  2',3'-dideoxy- and 2',3'-dideoxy-2',3'-didehydrocytidine (d2C and d4C) have been synthesized in good yields from 2'-deoxyuridine via dichlorinated derivatives 7a-b. The same synthetic strategy was used in the synthesis of d2C(Me) and d4C(Me) from thymidine. Following this method the evaluable 3'-chloro-2'-deoxycytidine derivatives 9 - 12 can easily be obtained.

  DOI：

  10.1080/07328319308018568
• 作为产物：
  描述：

  2-脱氧尿苷 、 三甲基乙酰氯 在 吡啶 作用下， 反应 3.0h， 以98%的产率得到O^5'-(2,2-dimethyl-propionyl)-2'-deoxy-uridine
  参考文献：
  名称：

  亚磷酰胺-亚磷酸三酯方法在氧化固醇与通过磷酸二酯键连接的核苷类似物之间的组合的合成中的应用

  摘要：

  用于固相DNA合成的最近开发的亚磷酰胺-亚磷酸三酯方法似乎是制备通过溶液中的磷酸二酯键连接的不稳定多功能化合物的选择技术。因此，为了使亲脂性氧固醇水溶性以用于生物学研究，我们使用Cβ-氰基乙氧基）双（二异丙胺）膦2作为磷酸化剂，制备了多氧固醇和核苷类似物之间的几种组合。这种方法在非常温和的条件下以相当高的收率（> 60％）提供了所需的1型化合物。

  DOI：

  10.1016/s0040-4020(01)85432-6

文献信息

• Synthesis, Crystal Structure, and Enzymatic Evaluation of a DNA-Photolesion Isostere
  作者：Jens Butenandt、André P. M. Eker、Thomas Carell

  DOI：10.1002/(sici)1521-3765(19980416)4:4<642::aid-chem642>3.0.co;2-k

  日期：1998.4.16

  Nucleotide analogues are useful tools for the investigation of interactions between DNA-binding proteins and DNA at a molecular level. Herein we describe the synthesis of the DNA-lesion analogue 2, which is required to determine the extent to which specific phosphodiesters in the DNA backbone contribute to the recognition of cyclobutane pyrimidine dimer DNA lesion by the dimer-specific repair enzymes DNA photolyases or T4-endonuclease V. The analogue 2 is a close structural mimic of cyclobutane pyrimidine dimers like 1. which are the major lesions induced upon irradiation of cells with UV light. Instead of the negatively charged phosphate link in 1, analogue 2 contains an uncharged but isosteric formacetal moiety. The analysis of this and other phosphodiester contacts is hoped to provide insight into the lesion recognition process, which is currently believed to require the nipping of the lesioned base out of the DNA double helix. The lesion analogue 2 is synthetically available in large quantities, which allowed us to establish a new, fast and sensitive DNA photolyase assay. A precise X-ray crystal structure analysis of the DNA-lesion analogue 2 is also presented. The structure underlines the isosteric character of 2 and reveals, in combination with the only other available X-ray crystal structure determined from a thymine-dimer triester analogue, interesting structural features of cyclobutane pyrimidine dimer lesions. We describe the incorporation of the lesion analogue 2 into oligonucleotides by using standard phosphoramidite chemistry. Initial enzymatic repair studies are reported with three different types of DNA photolyases. These studies show that the lesion analogue 2 is rapidly repaired by photolyases from Anacystis nidulans, Neurospora crassa and from the marsupial Potorous tridactylis. The enzymatic investigations indicate that all photolyases, including enzymes from higher organisms (Tridactylis) accept the formacetal dimer as a lesion substrate and therefore could possess a similar DNA-lesion recognition process, in which the interaction with the central phosphate unit is only of limited importance.
• JI, YU-HUA;BANNWARTH, WILLI;LUU, BANG, TETRAHEDRON, 46,(1990) N, C. 487-502
  作者：JI, YU-HUA、BANNWARTH, WILLI、LUU, BANG

  DOI：——

  日期：——
• Application of the phosphoramidite-phosphite triester approach for the synthesis of combinations between oxygenated sterols and nucleoside analogues linked by phosphodiester bonds
  作者：Yu-hua Jl、Willi Bannwarth、Bang Luu

  DOI：10.1016/s0040-4020(01)85432-6

  日期：1990.1

  synthesis seems to be the technique of choice for the preparation of labile multifunctional compounds linked by phosphodiester bonds in solution. Thus, to make the lipophilic oxysterols water-soluble for biological studies, we have prepared several combinations between polyoxygenated sterols and nucleoside analogues using Cβ-cyanoethoxy)bis(diisopropylamine) phosphine 2 as phosphorylating agent. This approach

  用于固相DNA合成的最近开发的亚磷酰胺-亚磷酸三酯方法似乎是制备通过溶液中的磷酸二酯键连接的不稳定多功能化合物的选择技术。因此，为了使亲脂性氧固醇水溶性以用于生物学研究，我们使用Cβ-氰基乙氧基）双（二异丙胺）膦2作为磷酸化剂，制备了多氧固醇和核苷类似物之间的几种组合。这种方法在非常温和的条件下以相当高的收率（> 60％）提供了所需的1型化合物。
• Improved Synthesis of 2′,3′-Dideoxycytidine (d2C) and Its Correlated Nucleoside Analogues
  作者：L. De Napoli、A. Messere、D. Montesarchio、G. Piccialli、C. Santacroce

  DOI：10.1080/07328319308018568

  日期：1993.11

  2',3'-dideoxy- and 2',3'-dideoxy-2',3'-didehydrocytidine (d2C and d4C) have been synthesized in good yields from 2'-deoxyuridine via dichlorinated derivatives 7a-b. The same synthetic strategy was used in the synthesis of d2C(Me) and d4C(Me) from thymidine. Following this method the evaluable 3'-chloro-2'-deoxycytidine derivatives 9 - 12 can easily be obtained.