CpU | 2382-64-1

• 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: CpU
• 英文别名: Cytidylyl-(3'-5')-uridin；Cytidylyl-(3'.5')-uridine；[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-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: 2382-64-1
• 化学式: C₁₈H₂₄N₅O₁₃P
• 分子量: 549.388
• InChiKey: VSIFECIDUDPNRC-NCOIDOBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.1
• 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：
  263
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  CpU 在 zinc(II) nitrate 、 sodium nitrate 、 HEPES buffer 作用下， 以 水 为溶剂， 生成 胞磷托定 、 尿嘧啶核苷
  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：

  在 正丙胺 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 CpU
  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。
• KOMIYAMA, MAKOTO, CARBOHYDR. RES., 192,(1989) C. 97-102
  作者：KOMIYAMA, MAKOTO

  DOI：——

  日期：——
• WU, TAIFENG;OGILVIE, KELVIN K., J. ORG. CHEM., 55,(1990) N5, C. 4717-4724
  作者：WU, TAIFENG、OGILVIE, KELVIN K.

  DOI：——

  日期：——
• Zn²⁺-Promoted Hydrolysis of 3′,5′-Dinucleoside Monophosphates and Polyribonucleotides. The Effect of Nearest Neighbours on the Cleavage of Phosphodiester Bonds
  作者：Satu Kuusela、Harri Lönnberg

  DOI：10.1080/07328319608002466

  日期：1996.10

  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.
• Chemical synthesis of RNA via 2′-O-cyanoethylated intermediates
  作者：Hisao Saneyoshi、Kaori Ando、Kohji Seio、Mitsuo Sekine

  DOI：10.1016/j.tet.2007.07.102

  日期：2007.11

  could be removed from 2′-O-cyanoethylated ribonucleoside derivatives by treatment with Bu4NF. This finding was successfully applied to the synthesis of oligoribonucleotides via their 2′-O-cyanoethylated derivatives as key intermediates where a cyanoethyl group was used as the 2′-hydroxyl protecting group. The rate of condensation using this protecting group in the presence of various activators was generally

  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。