N²,3',5'-triisobutyryl-2'-deoxyguanosine | 82921-42-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N²,3',5'-triisobutyryl-2'-deoxyguanosine
• 英文别名: [(2R,3S,5R)-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]-3-(2-methylpropanoyloxy)oxolan-2-yl]methyl 2-methylpropanoate
• CAS: 82921-42-4
• 化学式: C₂₂H₃₁N₅O₇
• 分子量: 477.517
• InChiKey: MDWHMJGTPYDBHV-RRFJBIMHSA-N

物化性质

• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  150
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N²,3',5'-triisobutyryl-2'-deoxyguanosine 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 17.67h， 生成 N2-异丁酰-5'-O-(4,4'-二甲氧基三苯基)-2'-脱氧鸟苷
  参考文献：
  名称：

  四个十氧代核糖核苷酸的简化液相制备及其初步光谱表征

  摘要：

  dApTpApTpApTpApTpApT，dApTpApTpCpGpApTpApT和dApApApApApApApApApTpTpTly化学合成了四个自互补的十氧杂核糖核苷酸dApTpApTpApTpApTpApT，dApTpApTpCpGpCpApTpApTply。努力集中于使过程尽可能简单，同时在该过程的每个步骤中获得高纯度的产品。根据以下方案，从3'-末端以3'- O-苯甲酰化的单体开始精加工十聚体：单体+单体二聚体+二聚体四聚体+二聚六聚体+四聚体十聚体。中间体和完全封闭的十聚体的纯度通过色谱法和300MHz 1 HN M R.光谱法进行监测。解封闭的十氧杂核糖核苷酸的特征在于它们的UV，CD和1 HNMR。光谱。

  DOI：

  10.1002/hlca.19820650803
• 作为产物：
  描述：

  N2,3',5'-triisobutyryl-O6-p-nitrophenylethyl-2'-deoxyguanosine 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 吡啶 为溶剂， 反应 1.0h， 以84%的产率得到N²,3',5'-triisobutyryl-2'-deoxyguanosine
  参考文献：
  名称：

  的p -nitrophenylethyl（NPE）组：一种多功能的新的保护基团为磷酸和核苷和核苷酸糖苷配基保护

  摘要：

  描述了用于合成寡核苷酸的新的单体结构单元的合成，该新的单体结构单元通过磷酸三酯方法进行合成，该方法包含对-硝基苯基乙基用于磷酸盐和糖苷配基的保护。在澳在鸟苷的酰胺官能团的阻断6可以通过Mitsunobu反应形成对应的O来实现6 - p -nitrophenylethyl衍生物（4，5，10）。糖保护胸苷（16）和尿苷（17）已经被在澳烷基化4以S Ñ 1型反应通过p在苯，以形成将O碳酸盐-nitrophenylethyl碘化银4 - p -nitrophenylethyl衍生物（18，19）。在-2'-脱氧胞苷（氨基的保护25）和胞苷（26）可以通过1-（直接进行p -nitrophenylethoxycarbonyl） -苯并三唑的DMF，得到相应的氨基甲酸酯（27，28）作为一种新的类型为N 4-酰化胞苷衍生物。p 2'-脱氧腺苷（33）和腺苷（34）中氨基的硝基苯基乙氧基羰基化作用需

  DOI：

  10.1016/0040-4020(84)85103-0

文献信息

• Preparation of Spin-Labeled-2-Amino-dA, dA, dC and 5-Methyl-dC Phosphoramidites for the Automatic Synthesis of EPR Active Oligonucleotides
  作者：Cesare Giordano、Federica Fratini、Donato Attanasio、Luciano Cellai

  DOI：10.1055/s-2001-12355

  日期：——

  2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (TEMPO) labeled phosphoramidites of 2-amino-dA, dA, dC and 5-methyl-dC were synthesized and used for the automatic synthesis of mono-labeled oligodeoxynucleotides (ODNs), which proved active to EPR. It is now possible to insert a paramagnetic probe into nucleic acids in a site- and type-specific manner. The combination of this synthetic approach with EPR spectroscopy can be exploited for performing studies on dynamics and local structural modifications in nucleic acids.

  合成了2,2,6,6-四甲基-1-哌啶氧自由基（TEMPO）标记的2-氨基-dA、dA、dC和5-甲基-dC的磷酰胺类化合物，并用于单标记寡脱氧核苷酸（ODNs）的自动合成，这些化合物对电子顺磁共振（EPR）表现出活性。现在可以以特定的位置和类型将顺磁探针插入核酸中。这种合成方法与EPR光谱的结合可以用于研究核酸中的动态变化和局部结构修饰。
• MICROWAVE ASSISTED HIGH YIELDING PREPARATION OF<i>N</i>-PROTECTED 2′-DEOXYRIBONUCLEOSIDES USEFUL FOR OLIGONUCLEOTIDE SYNTHESIS
  作者：N. S. Rao、P. Kumar、V. K. Chauhan、B. S. Garg、K. C. Gupta

  DOI：10.1081/ncn-120006833

  日期：2002.7

  A rapid and high yielding method for the synthesis of precursors of synthons for DNA synthesis, N-protected 2'-deoxyribonucleosides is described, which occur under mild conditions using microwave irradiation. The desired material, N-protected nucleosides, was obtained in 93-96% yield in few minutes. The final products were then characterized by 1H-NMR and MALDI-TOF and compared with the standard samples

  描述了一种快速且高产率的合成用于DNA合成的合成子前体N保护的2'-脱氧核糖核苷的方法，其在温和条件下使用微波辐射发生。在几分钟内以93-96％的收率获得了所需的物质N保护的核苷。然后通过1 H-NMR和MALDI-TOF对最终产物进行表征，并与标准样品进行比较。该方法适合于小至中等规模的合成。
• Production method of 2'-deoxyguanosine compound
  申请人：Ajinomoto Co., Inc.

  公开号：EP1683806A1

  公开（公告）日：2006-07-26

  The present invention provides a production method of a 2'-deoxyguanosine compound represented by the following formula (2), which includes a step of desulfurization reaction of an 8,2'-anhydro-8-mercapto-9-β-arabinofuranosylguanine compound represented by the following formula (1) in a solvent in the presence of a base using nickel or a nickel alloy. wherein R1, R2, R4 and R5 are each independently a hydrogen atom or a hydroxyl-protecting group, and R3 and R6 are hydrogen atoms or amino-protecting groups.

  本发明提供了一种通过在溶剂中在碱的存在下使用镍或镍合金对以下式（1）表示的8,2'-脱硫-8-巯基-9-β-阿拉伯呋喃核苷鸟嘌呤化合物进行脱硫反应的生产方法，从而得到以下式（2）表示的2'-去氧鸟苷化合物。其中R1、R2、R4和R5分别独立地是氢原子或羟基保护基，R3和R6是氢原子或氨基保护基。
• Pyridyloxobutyl Adduct <i>O</i>⁶-[4-Oxo-4-(3-pyridyl)butyl]guanine Is Present in 4-(Acetoxymethylnitrosamino)-1-(3-pyridyl)-1-butanone-Treated DNA and Is a Substrate for <i>O</i>⁶-Alkylguanine-DNA Alkyltransferase
  作者：Lijuan Wang、Thomas E. Spratt、Xiao-Keng Liu、Stephen S. Hecht、Anthony E. Pegg、Lisa A. Peterson

  DOI：10.1021/tx9602067

  日期：1997.5.1

  prepared. This adduct was stable at pH 7.0 for greater than 13 days and to neutral thermal hydrolysis conditions (pH 7.0, 100 degrees C, 30 min). Under mild acid hydrolysis conditions (0.1 N HCl, 80 degrees C), O6-pobdG was depurinated to yield O6-[4-oxo-4-(3-pyridyl)butyl]guanine (O6-pobG). O6-pobdG was hydrolyzed to 4-hydroxy-1-(3-pyridyl)-1-butanone and guanine under strong acid hydrolysis conditions

  肺致癌物4-（甲基亚硝胺基）-1-（3-吡啶基）-1-丁酮（NNK）被活化为甲基化或吡啶基氧代丁基化DNA的反应性代谢产物。先前的研究表明，吡啶基氧代丁基化的DNA会干扰O6-烷基鸟嘌呤-DNA烷基转移酶（AGT）对O6-甲基鸟嘌呤（O6-mG）的修复。吡啶基氧代丁基化DNA的AGT反应性归因于（吡啶基氧代丁基）鸟嘌呤加合物。制备了一种潜在的AGT底物加合物2'-脱氧-O6- [4-氧代-4-（3-吡啶基）丁基]鸟苷（O6-pobdG）。该加合物在pH 7.0稳定超过13天，并在中性热水解条件（pH 7.0，100摄氏度，30分钟）下稳定。在温和的酸水解条件下（0.1 N HCl，80摄氏度），将O6-pobdG脱嘌呤化，以生成O6- [4-氧代-4-（3-吡啶基）丁基]鸟嘌呤（O6-pobG）。在强酸水解条件（0.8 N HCl，80摄氏度）下，O6-pobdG水解为4-羟基-1-（3-
• Electron Paramagnetic Resonance (EPR) Study of Spin-Labeled Camptothecin Derivatives: A Different Look of the Ternary Complex
  作者：Antonio Ricci、Jessica Marinello、Marco Bortolus、Albert Sánchez、Anna Grandas、Enrique Pedroso、Yves Pommier、Giovanni Capranico、Anna Lisa Maniero、Giuseppe Zagotto

  DOI：10.1021/jm101232t

  日期：2011.2.24

  Camptothecin (CPT) derivatives are clinically effective poisons of DNA topoisomerase I (Top 1) able to form a ternary complex with the Top1 DNA complex. The aim of this investigation was to examine the dynamic aspects of the ternary complex formation by means of site-directed spin labeling electron paramagnetic resonance (SDSL-EPR). Two semisynthetic CPT derivatives bearing the paramagnetic moiety were synthesized, and their biological activity was tested. A 22-mer DNA oligonucleotide sequence with high affinity cleavage site for Top1 was also synthesized. EPR experiments were carried out on modified CPT in the presence of DNA, of Top1, or of both. In the last case, a slow motion component in the EPR signal appeared, indicating the formation of the ternary complex. Deconvolution of the EPR spectrum allowed to obtain the relative drug amounts in the complex. It was also possible to demonstrate that the residence time of CPT "trapped" in the ternary complex is longer than hundreds of microseconds.