鸟苷酰-(3'-5')-尿苷 | 4785-07-3

• 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
• 中文名称: 鸟苷酰-(3'-5')-尿苷
• 英文名称: Guanylyl-(3'-5')-uridin
• 英文别名: Guanylyl(3'-5')uridine；[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate
• CAS: 4785-07-3
• 化学式: C₁₉H₂₄N₇O₁₃P
• 分子量: 589.412
• InChiKey: HQXUOLIEBGPXRE-VMIOUTBZSA-N

物化性质

• 密度：
  2.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.4
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  290
• 氢给体数：
  8
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  鸟苷酰-(3'-5')-尿苷 在 高氯酸四甲基铵 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 生成 guanosine 2',3'-cyclic monophosphate 、 尿嘧啶核苷
  参考文献：
  名称：

  Guanidine based self-assembled monolayers on Au nanoparticles as artificial phosphodiesterases

  摘要：

  金纳米颗粒经过鸟嘌呤基催化单层保护后，在磷酸二酯裂解中表现出高的协同作用和效率。

  DOI：

  10.1039/c4ra03150d
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 鸟苷酰-(3'-5')-尿苷
  参考文献：
  名称：

  通过2'- O-氰基乙基化中间体化学合成RNA

  摘要：

  发现通过用Bu 4 NF处理可以从2'- O-氰基乙基化的核糖核苷衍生物中除去2'- O-氰基乙基。该发现通过其2'- O-氰基乙基化衍生物作为关键中间体成功地应用于寡核糖核苷酸的合成，其中氰基乙基被用作2'-羟基保护基。在各种活化剂存在下，使用该保护基的缩合速率通常比将TBDMS基团用作保护基时观察到的速率要快。

  DOI：

  10.1016/j.tet.2007.07.102

文献信息

• Some observations relating to the use of 1-aryl-4-alkoxypiperidin-4-yl groups for the protection of the 2′-hydroxy functions in the chemical synthesis of oligoribonucleotides
  作者：Wayne Lloyd、Colin B. Reese、Quanlai Song、Anthony M. Vandersteen、Cristina Visintin、Pei-Zhou Zhang

  DOI：10.1039/a908149f

  日期：——

  The comparative rates of acid-catalysed removal of ten 1-aryl-4-methoxypiperidin-4-yl 8 (R = Me) [including the previously reported Ctmp 5 and Fpmp 6] protecting groups for the 2′-hydroxy functions in oligoribonucleotide synthesis are discussed. These studies have led to the development of the 1-(4-chlorophenyl)-4-ethoxypiperidin-4-yl (Cpep) protecting group 8 (R = Et, R1 = R2 = H, R3 = Cl) which is both more stable than the Ctmp and Fpmp groups at pH 0.5 and more labile at pH 3.75. The influence of the ribonucleoside aglycone on the stability of the 2′-O-Fpmp and 2′-O-Ctmp protecting groups both at low and high pH is examined.

  讨论了在寡核苷酸合成中，十个1-芳基-4-甲氧基哌啶-4-基（R = Me，包括先前报道的Ctmp 5和Fpmp 6）保护基对2'-羟基功能的酸催化去除的相对速率。这些研究导致开发了1-(4-氯苯基)-4-乙氧基哌啶-4-基（Cpep）保护基8（R = Et，R1 = R2 = H，R3 = Cl），其在pH 0.5下比Ctmp和Fpmp群更加稳定，而在pH 3.75下更加不稳定。研究了核苷酸基在低pH和高pH下对2'-O-Fpmp和2'-O-Ctmp保护基稳定性的影响。
• Guanidine-Based Polymer Brushes Grafted onto Silica Nanoparticles as Efficient Artificial Phosphodiesterases
  作者：Claudia Savelli、Riccardo Salvio

  DOI：10.1002/chem.201406526

  日期：2015.4.7

  Polymer brushes grafted to the surface of silica nanoparticles were fabricated by atom‐transfer radical polymerization (ATRP) and investigated as catalysts in the cleavage of phosphodiesters. The surfaces of silica nanoparticles were functionalized with an ATRP initiator. Surface‐initiated ATRP reactions, in varying proportions, of a methacrylate moiety functionalized with a phenylguanidine moiety

  通过原子转移自由基聚合（ATRP）制备了接枝到二氧化硅纳米颗粒表面的聚合物刷，并研究了其作为磷酸二酯裂解的催化剂。二氧化硅纳米颗粒的表面用ATRP引发剂官能化。表面引发的ATRP反应以不同的比例被苯基胍部分官能化的甲基丙烯酸酯部分和惰性的亲水性甲基丙烯酸酯物质提供了杂化的纳米颗粒，并通过电位滴定，热重分析和SEM对其进行了表征。在RNA模型化合物2-羟丙基对位酯的酯交换反应中测试了杂化纳米颗粒的活性-硝基苯基磷酸酯（HPNP）和二核糖核苷单磷酸酯。较高的催化效率和显着的有效摩尔浓度，从而克服了先前在可比系统中观察到的有效摩尔浓度，表明在胍/胍单元中存在有效的协同作用，并且在纳米结构中存在高度的预组织。所研究的系统还对二核糖核苷序列CpA表现出显着和前所未有的选择性。提出的结果为制备超分子催化剂的新颖而直接的策略开辟了道路。
• 一种烷基化核苷、核苷酸、寡核苷酸及其类似物的制备方法
  申请人：上海交通大学

  公开号：CN117343119A

  公开（公告）日：2024-01-05

  本发明提供了一种烷基化核苷、核苷酸、寡核苷酸或其类似物的制备方法，包括以下步骤：将核苷底物与R2B(OH)2或R2BF3K加入溶剂中溶解，然后加入氧化剂和添加剂，在光照或非光照条件下反应，即得；其中，所述核苷底物为核苷、核苷酸、寡核苷酸或其类似物；所述R2B(OH)2或R2BF3K中，R2选自烷基、烷氧基、芳烷基、环烷基、烯烷基、炔烷基、烷基卤素及以下基团：#imgabs0##imgabs1#本发明设计了一种合成烷基化核苷、核苷酸、寡核苷酸及其类似物的新路径，以核苷、核苷酸、寡核苷酸及其类似物为原料，通过C‑H键的官能团化反应制成。该制备方法简单，易于操作，反应条件温和，避免了高温的苛刻条件及有毒试剂的使用，对环境友好。
• Catalysis of Diribonucleoside Monophosphate Cleavage by Water Soluble Copper(II) Complexes of Calix[4]arene Based Nitrogen Ligands
  作者：Roberta Cacciapaglia、Alessandro Casnati、Luigi Mandolini、David N. Reinhoudt、Riccardo Salvio、Andrea Sartori、Rocco Ungaro

  DOI：10.1021/ja0632106

  日期：2006.9.1

  Calix[4]arenes functionalized at the 1,2-, 1,3-, and 1,2,3-positions of the upper rim with [12]ane-N-3 ligating units were synthesized, and their bi-and trimetallic zinc(II) and copper( II) complexes were investigated as catalysts in the cleavage of phosphodiesters as RNA models. The results of comparative kinetic studies using monometallic controls indicate that the subunits of all of the zinc(II) complexes and of the 1,3-distal bimetallic copper(II) complex 7-Cu-2 act as essentially independent monometallic catalysts. The lack of cooperation between metal ions in the above complexes is in marked contrast with the behavior of the 1,2-vicinal bimetallic copper(II) complex 6-Cu-2, which exhibits high catalytic efficiency and high levels of cooperation between metal ions in the cleavage of HPNP and of diribonucleoside monophosphates NpN'. A third ligated metal ion at the upper rim does not enhance the catalytic efficiency, which excludes the simultaneous cooperation in the catalysis of the three metal ions in 8-Cu-3. Rate accelerations relative to the background brought about by 6-Cu-2 and 8-Cu-3 (1.0 mM catalyst, water solution, pH 7.0, 50 degrees C) are on the order of 10(4)-fold, largely independent of the nucleobase structure, with the exception of the cleavage of diribonucleoside monophosphates in which the nucleobase N is uracil, namely UpU and UpG, for which rate enhancements rise to 10(5)-fold. The rationale for the observed selectivity is discussed in terms of deprotonation of the uracil moiety under the reaction conditions and complexation of the resulting anion with one of the copper(II) centers.
• Réactions synthétiques par la ribonucléase T1
  作者：Kimiko Sato-Asano、Fujio Egami

  DOI：10.1016/0006-3002(58)90032-5

  日期：1958.9