5'-O-(4,4'-dimethoxytrityl)-5-methoxycarbonyl-N4-acetyl-2'-deoxycytidine 3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite | 1311141-26-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5'-O-(4,4'-dimethoxytrityl)-5-methoxycarbonyl-N4-acetyl-2'-deoxycytidine 3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite
• 英文别名: 3'-(diisopropylaminocyanoethoxyphosphino)-5'-(dimethoxytrityl)-5-carboxymethyl-2'deoxycytidine；methyl 4-acetamido-1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyoxolan-2-yl]-2-oxopyrimidine-5-carboxylate
• CAS: 1311141-26-0
• 化学式: C₄₃H₅₂N₅O₁₀P
• 分子量: 829.887
• InChiKey: MHZBQRNJXOQFTL-KRPTXEAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  59
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  171
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  5-碘-2'-脱氧胞苷 在 吡啶 、 tris-(dibenzylideneacetone)dipalladium(0) 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.5h， 生成 5'-O-(4,4'-dimethoxytrityl)-5-methoxycarbonyl-N4-acetyl-2'-deoxycytidine 3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite
  参考文献：
  名称：

  Catalytic Space Engineering as a Strategy to Activate C–H Oxidation on 5-Methylcytosine in Mammalian Genome

  摘要：

  DOI：

  10.1021/jacs.1c03815

文献信息

• Improved Synthesis and Mutagenicity of Oligonucleotides Containing 5-Hydroxymethylcytosine, 5-Formylcytosine and 5-Carboxylcytosine
  作者：Martin Münzel、Ulrike Lischke、Dimitrios Stathis、Toni Pfaffeneder、Felix A. Gnerlich、Christian A. Deiml、Sandra C. Koch、Konstantin Karaghiosoff、Thomas Carell

  DOI：10.1002/chem.201102782

  日期：2011.12.2

  5‐Formylcytosine (fC or 5‐CHOdC) and 5‐carboxylcytosine (caC or 5‐COOHdC) have recently been identified as constituents of mammalian DNA. The nucleosides are formed from 5‐methylcytosine (mC or 5‐MedC) via 5‐hydroxymethylcytosine (hmC or 5‐HOMedC) and are possible intermediates of an active DNA demethylation process. Here we show efficient syntheses of phosphoramidites which enable the synthesis of

  最近已鉴定出5-甲酰基胞嘧啶（fC或5-CHO dC）和5-羧基胞嘧啶（caC或5-COOH dC）是哺乳动物DNA的成分。核苷由5-甲基胞嘧啶（mC或5-Me dC）经由5-羟甲基胞嘧啶（hmC或5-HOMe dC）形成，并且可能是活性DNA去甲基化过程的中间体。在这里，我们显示了亚磷酰胺的有效合成方法，该方法能够合成包含这些基于Pd 0的胞嘧啶修饰的DNA链5-碘代脱氧胞苷的催化功能化。fC的第一个晶体结构表明，在环外胺和甲酰基之间存在分子内H键，该键控制甲酰基取代基的构象。使用新设计的体外诱变试验，我们显示fC和caC只是轻微诱变，这是碱基充当表观遗传控制单位的前提。
• Syntheses of 5-Formyl- and 5-Carboxyl-dC Containing DNA Oligos as Potential Oxidation Products of 5-Hydroxymethylcytosine in DNA
  作者：Qing Dai、Chuan He

  DOI：10.1021/ol201189n

  日期：2011.7.1

  To investigate the potential oxidation products of 5-hydroxymethylcytosine (5-hmC)-containing DNA, we present here efficient syntheses of 5-formyl- and 5-methoxycarbonyl-2'-deoxycytidine phosphoramidites. The 5-formyl group in III was easy to introduce and was compatible with phosphoramidite and DNA syntheses. An additional treatment of ODN1 with NaBH4 produced the corresponding ODN2 quantitatively. Phosphoramidite V was also incorporated into DNA, and the methyl ester could be hydrolyzed under mild basic conditions to afford ODN3.
• Catalytic Space Engineering as a Strategy to Activate C–H Oxidation on 5-Methylcytosine in Mammalian Genome
  作者：Sushma Sappa、Debasis Dey、Babu Sudhamalla、Kabirul Islam

  DOI：10.1021/jacs.1c03815

  日期：2021.8.11