cytidylyl-(3'->5')-cytidine | 2536-99-4

• 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: cytidylyl-(3'->5')-cytidine
• 英文别名: d(C)2；3'-C-C-5'；Cp(3'-5')C；Cytidylyl-(3'-5')-cytidine；[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl [(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate
• CAS: 2536-99-4
• 化学式: C₁₈H₂₅N₆O₁₂P
• 分子量: 548.403
• InChiKey: PTLMIIUMLITBQT-NCOIDOBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.5
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  273
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  cytidylyl-(3'->5')-cytidine 在 zinc(II) nitrate 、 sodium nitrate 、 HEPES buffer 作用下， 以 水 为溶剂， 生成 胞磷托定 、 胞苷
  参考文献：
  名称：

  Zn²⁺-Promoted Hydrolysis of 3′,5′-Dinucleoside Monophosphates and Polyribonucleotides. The Effect of Nearest Neighbours on the Cleavage of Phosphodiester Bonds

  摘要：

  Pseudo first-order rate constants for the Zn2+-promoted cleavage of 15 different monophosphates, 4 different ribo homopolymers and RNA III from baker's yeast have been determined. Furthermore, the distribution of various nucleosides at the 3'-and 5'-terminus of the oligomeric hydrolysis products of RNA has been quantified. On these bases, the effect of nearest neighbours on the metal-ion-promoted hydrolysis of the internucleosidic phosphodiester bonds of RNA is discussed.

  DOI：

  10.1080/07328319608002466
• 作为产物：
  描述：

  4-N-benzoyl-2'-O-tetrahydropyranyl-5'-O-dimethoxytritylcytidine 在 盐酸 、 喹啉-8-磺酰氯 、 氨 、 对甲苯磺酸 、 zinc(II) chloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.25h， 生成 cytidylyl-(3'->5')-cytidine
  参考文献：
  名称：

  A convenient method for insertion of the 5'-terminal phosphate group in the triester approach to oligoribonucleotide synthesis

  摘要：

  DOI：

  10.1021/jo01304a042

文献信息

• Rapid and highly base selective RNA cleavage by a dinuclear Cu(II) complex
  作者：Shanghao Liu、Andrew D. Hamilton

  DOI：10.1039/a808195f

  日期：——

  A bis-Cu(II) complex based on a covalently linked terpyridine and bipyridine ligand system is shown to rapidly cleave bis-ribonucleotides with remarkable selectivity for adenine bases.

  基于共价连接的吡啶并三吡啶和联吡啶配体系统的二铜(II)配合物，显示出对腺嘌呤基具有显著选择性的双核糖核酸快速切割能力。
• Dinuclear Zn²⁺complexes in the hydrolysis of the phosphodiester linkage in a diribonucleoside monophosphate diester
  作者：Morio Yashiro、Hideki Kaneiwa、Kenichi Onaka、Makoto Komiyama

  DOI：10.1039/b312301d

  日期：——

  Dizinc complexes that were formed from 2 ∶ 1 mixtures of Zn(NO3)2 and dinucleating ligands TPHP (1), TPmX (2) or TPpX (3) in aqueous solutions efficiently hydrolyzed diribonucleoside monophosphate diesters (NpN) under mild conditions. The dinucleating ligand affected the structure of the aquo-hydroxo-dizinc core, resulting in different characteristics in the catalytic activities towards NpN cleavage. The pH-rate profile of ApA cleavage in the presence of (Zn2+)2-1 was sigmoidal, whereas those of (Zn2+)2-2 and (Zn2+)2-3 were bell-shaped. The pH titration study indicated that (Zn2+)2-1 dissociates only one aquo proton (up to pH 12), whereas (Zn2+)2-2 dissociates three aquo protons (up to pH 10.7). The observed differences in the pH-rate profile are attributable to the various distributions of the monohydroxo-dizinc species, which are responsible for NpN cleavage. As compared to that using (Zn2+)2-1, the NpN cleavage using (Zn2+)2-2 showed a greater rate constant, with a higher product ratio of 3′-NMP/2′-NMP. The saturation behaviors of the rate, with regard to the concentration of NpN, were analyzed by Michaelis–Menten type kinetics. Although the binding of (Zn2+)2-2 to ApA was weaker than that of (Zn2+)2-1, (Zn2+)2-2 showed a greater kcat value than (Zn2+)2-1, resulting in higher ApA cleavage activity of the former.

  由2:1的Zn(NO3)2与双配体TPHP（1）、TPmX（2）或TPpX（3）在水溶液中形成的二锌复合物在温和条件下有效水解二核苷酸单磷酸二酯（NpN）。双配体的结构影响了水合羟基二锌核心的构造，导致其催化NpN裂解的活性特征有所不同。在（Zn2+)2-1存在下，ApA裂解的pH-速率曲线呈S型，而（Zn2+)2-2和（Zn2+)2-3的曲线则呈钟形。pH滴定研究表明，（Zn2+)2-1仅在pH达到12时解离一个水合质子，而（Zn2+)2-2在pH达到10.7时则解离三个水合质子。观察到的pH-速率曲线差异可归因于单羟基二锌物种的不同分布，这些物种是NpN裂解的关键。与使用（Zn2+)2-1相比，使用（Zn2+)2-2时的NpN裂解表现出更大的速率常数，且3′-NMP/2′-NMP的产物比例更高。关于NpN浓度的速率饱和行为通过米氏动力学分析。尽管（Zn2+)2-2对ApA的结合强度弱于（Zn2+)2-1，但（Zn2+)2-2的kcat值高于（Zn2+)2-1，导致前者在ApA裂解中的活性更强。
• Preparation and Properties of Oligocytidylates with 2′–5′ Internucleotide Linkage
  作者：Hiroaki Sawai、Masaji Ohno

  DOI：10.1246/bcsj.58.361

  日期：1985.1

  polymerization of cytidine 5′-phosphorimidazolide in aqueous solution. 2′–5′ internucleotide linkage was preferentially formed. The yields of the 2′–5′ linked dimer, trimer, tetramer and pentamer were 17.0, 5.5, 1.9, and 0.7%, respectively. Some of their properties were studied by NMR, CD, UV, and chromatography and compared with the corresponding 3′–5′ linked oligomers which were prepared enzymatically.

  通过铅（II）离子催化聚合胞苷 5'-磷咪唑啉在水溶液中制备了五聚体的寡核苷酸。优先形成 2'-5' 核苷酸间连接。2'-5' 连接的二聚体、三聚体、四聚体和五聚体的产率分别为 17.0、5.5、1.9 和 0.7%。通过 NMR、CD、UV 和色谱法研究了它们的一些特性，并与酶法制备的相应 3'-5' 连接的低聚物进行了比较。
• Kamitani, Jun; Sumaoka, Jun; Asanuma, Hiroyuki, Journal of the Chemical Society. Perkin Transactions 2 (2001), 1998, # 3, p. 523 - 527
  作者：Kamitani, Jun、Sumaoka, Jun、Asanuma, Hiroyuki、Komiyama, Makoto

  DOI：——

  日期：——
• 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.