2'-deoxycytidine homodimer | 26467-01-6

• 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: 2'-deoxycytidine homodimer
• 英文别名: d(CpC)；d；Deoxyadenylyladenosin-monophosphat；Desoxycytidylyl-(3'->5')-desoxycytidin；2'-deoxy-cytidylyl-(5'->3')-2'-deoxy-cytidine；[(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-2-(hydroxymethyl)oxolan-3-yl] [(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl hydrogen phosphate
• CAS: 26467-01-6
• 化学式: C₁₈H₂₅N₆O₁₀P
• 分子量: 516.404
• InChiKey: IURHMJAVRZRPAH-PHEULEMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.5
• 重原子数：
  35
• 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：
  232
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2'-deoxycytidine homodimer 在 air 、 甲萘醌 作用下， 以 水 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  单电子光氧化诱导的 d(CpC) 中新型交联损伤的分离和表征¶

  摘要：

  摘要 最近我们报道了 d(CpC) 中两个相邻胞嘧啶之间形成的新型交联损伤的鉴定和表征，这是 d(CpC) 在 2-methyl-1 存在下 365 nm 光照射后形成的主要产物。 ,4-萘醌。在这项研究中，我们讨论了在相同照射条件下形成的另一个交联病变的隔离和结构表征。电喷雾电离质谱、串联质谱和二维核Overhauser效应光谱结果表明5'胞嘧啶的C6碳原子和3'胞嘧啶的N3氮原子共价键合。此外，5'胞嘧啶部分脱氨基，该胞嘧啶中的C5碳原子被氧化成羰基。

  DOI：

  10.1562/2003-12-15-ra-029.1
• 作为产物：
  描述：

  5'-O-(di-p-methoxytrityl)-4-N-(N-methylpyrrolidin-2-ylidene)-2'-deoxycytidine 在 1,2-环氧丁烷 、 四氮唑 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 2'-deoxycytidine homodimer
  参考文献：
  名称：

  Synthesis of Oligo(Deoxyribonucleoside Phosphorodithioate)s by the Dithiaphospholane Approach

  摘要：

  A novel method of synthesis of oligo(deoxyribonucleoside phosphorodithioate)s (S-2-ODNs), based on the ring-opening condensation of nucleoside 3'-0-(2-thiono-1,3,2-dithiaphospholane)s with 5'-O-deprotected nucleosi(ti)des in the presence of a strong organic base such as DBU, is presented. The process has been adapted to the requirements of automated solid-phase oligonucleotide synthesis with a relatively short condensation step (5 min) and reasonable step-yield(>95%). N-Methylpyrrolidin-2-ylidenyl (Pya) was found to be the group of choice for the protection of reactive aminofunctions of nucleobases in nucleotide substrates. Sarcosine-containing linker (LCA CPG SAR) was employed due to its known resistance to cleavage by DBU. Several medium-size S-2-ODNs were prepared by this approach. Their identity and purity was confirmed by means of P-31 NMR, gel electrophoresis, and mass spectrometry. It has been demonstrated that, contrary to a recent report, S-2-ODNs are not degraded by DNaseI.

  DOI：

  10.1021/jo00126a060

文献信息

• Synthesis of oligonucleotides via phosphoramidite approach utilizing 2-diphenylmethylsilylethyl (DPSE) as a phosphorus protecting group
  作者：Vasulinga T. Ravikumar、Tadeusz K. Wyrzykiewicz、Douglas L. Cole

  DOI：10.1016/s0040-4020(01)85503-4

  日期：——

  2-Diphenylmethylsilylethyl (DPSE) is a new protecting group for internucleotidic bonds in the synthesis of oligodeoxyribo nucleotides by the phosphoramidite approach. This group is stable to acidic conditions and can be removed under mild β-fragmentation conditions using aqueous ammonium hydroxide.

  2-二苯基甲基甲硅烷基乙基（DPSE）是通过亚磷酰胺方法合成寡脱氧核糖核苷酸中核苷酸间键的新保护基。该基团在酸性条件下稳定，可以在温和的β片段化条件下使用氢氧化铵水溶液除去。
• Synthesis and physicochemical studies of partially phosphate-methylated oligodeoxyribonucleotides
  作者：Serge Vinogradov、Ulysse Asseline、Thanh Thuong Nguyen

  DOI：10.1016/s0040-4039(00)73809-3

  日期：1993.9

  Partially phosphate-methylated oligodeoxyribonucleotides have been synthesized on an oxalyl-CPG derivatized support using an isopropoxyacetyl group for the protection of the exocyclic amine of the nucleic bases. Hybridization properties with the target sequence have been studied by absorption spectroscopy.
• Synthesis of Oligo(Deoxyribonucleoside Phosphorodithioate)s by the Dithiaphospholane Approach
  作者：Andrzej Okruszek、Agnieszka Sierzcha-la、Karen L. Fearon、Wojciech J. Stec

  DOI：10.1021/jo00126a060

  日期：1995.10

  A novel method of synthesis of oligo(deoxyribonucleoside phosphorodithioate)s (S-2-ODNs), based on the ring-opening condensation of nucleoside 3'-0-(2-thiono-1,3,2-dithiaphospholane)s with 5'-O-deprotected nucleosi(ti)des in the presence of a strong organic base such as DBU, is presented. The process has been adapted to the requirements of automated solid-phase oligonucleotide synthesis with a relatively short condensation step (5 min) and reasonable step-yield(>95%). N-Methylpyrrolidin-2-ylidenyl (Pya) was found to be the group of choice for the protection of reactive aminofunctions of nucleobases in nucleotide substrates. Sarcosine-containing linker (LCA CPG SAR) was employed due to its known resistance to cleavage by DBU. Several medium-size S-2-ODNs were prepared by this approach. Their identity and purity was confirmed by means of P-31 NMR, gel electrophoresis, and mass spectrometry. It has been demonstrated that, contrary to a recent report, S-2-ODNs are not degraded by DNaseI.
• Isolation and Characterization of a Novel Cross-link Lesion in d(CpC) Induced by One-electron Photooxidation¶
  作者：Zhenjiu Liu、Yuan Gao、Yu Zeng、Fang Fang、Dahn Chi、Yinsheng Wang

  DOI：10.1562/2003-12-15-ra-029.1

  日期：——

  Abstract Recently we reported the identification and characterization of a novel cross-link lesion formed between two adjacent cytosines in d(CpC), which is the major product formed upon 365 nm photoirradiation of d(CpC) in the presence of 2-methyl-1,4-naphthoquinone. In this study we discuss the isolation and structure characterization of another cross-link lesion formed under the same irradiation

  摘要 最近我们报道了 d(CpC) 中两个相邻胞嘧啶之间形成的新型交联损伤的鉴定和表征，这是 d(CpC) 在 2-methyl-1 存在下 365 nm 光照射后形成的主要产物。 ,4-萘醌。在这项研究中，我们讨论了在相同照射条件下形成的另一个交联病变的隔离和结构表征。电喷雾电离质谱、串联质谱和二维核Overhauser效应光谱结果表明5'胞嘧啶的C6碳原子和3'胞嘧啶的N3氮原子共价键合。此外，5'胞嘧啶部分脱氨基，该胞嘧啶中的C5碳原子被氧化成羰基。