5'-O-DMT-5-(3-trifluoroacetylaminoprop-1-enyl)-2'-deoxyuridine | 115794-56-4

• 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-DMT-5-(3-trifluoroacetylaminoprop-1-enyl)-2'-deoxyuridine
• 英文别名: (E)-5'-O-[Bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-5-[3-[(trifluoroacetyl)amino]-1-propenyl]uridine；N-[(E)-3-[1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-2,4-dioxopyrimidin-5-yl]prop-2-enyl]-2,2,2-trifluoroacetamide
• CAS: 115794-56-4
• 化学式: C₃₅H₃₄F₃N₃O₈
• 分子量: 681.665
• InChiKey: DJJQNJQSPYAYPU-GKJYNYMUSA-N

物化性质

• 密度：
  1.365±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  49
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  136
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  5'-O-DMT-5-(3-trifluoroacetylaminoprop-1-enyl)-2'-deoxyuridine 在 ammonium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 (E)-N-[(E)-3-[1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-2,4-dioxopyrimidin-5-yl]prop-2-enyl]-3-(1H-imidazol-5-yl)prop-2-enamide
  参考文献：
  名称：

  具有扩展化学功能的 DNA 酶对 RNA 的切割

  摘要：

  体外选择技术被应用于开发含有三个催化必需咪唑基团并催化 RNA 底物裂解的 DNA 酶。用于选择的核酸文库是通过聚合酶催化掺入 C5-咪唑功能化脱氧尿苷代替胸苷来构建的。化学合成用于定义仅由 12 个残基组成的最小化催化域。催化域形成紧凑的发夹结构，显示三个含咪唑的残基。通过简单改变围绕催化结构域的两个底物识别结构域，该酶可以切割几乎任何序列的 RNA。该酶在微摩尔浓度的 Zn2+ 存在下以多次周转运行，表现出饱和动力学和大于 1 min-1 的催化速率。含咪唑的 DNA 酶是已知最小的核酸酶之一，它将核酸酶的底物识别特性和蛋白质酶的化学功能结合在一个小分子中，但用途广泛且催化效率高。

  DOI：

  10.1021/ja993688s
• 作为产物：
  描述：

  N-烯丙基-2,2,2-三氟乙酰胺 在 吡啶 、 potassium tetrachloropalladate(II) 、 sodium acetate 、 三乙胺 作用下， 反应 76.0h， 生成 5'-O-DMT-5-(3-trifluoroacetylaminoprop-1-enyl)-2'-deoxyuridine
  参考文献：
  名称：

  Toward an RNaseA Mimic:  A DNAzyme with Imidazoles and Cationic Amines

  摘要：

  Site-specific RNA cleavage has received considerable attention over the years. Directed synthesis to append imidazoles or amines or both to oligonucleotides to target specific RNA cleavage represents an exciting avenue of research. However, to date catalysis by such synthetic constructs, particularly in terms of turnover, has been difficult to observe. This is the first report of a truly catalytic M2+-independent DNAzyme synthetically modified with imidazoles and cationic amines that would seem to mimic RNaseA. This work now demonstrates how synthetic organic chemistry, when merged with combinatorial selection, can result in a new class of DNAzymes that meets the ongoing synthetic challenges for developing relatively small biomimetic catalysts.

  DOI：

  10.1021/ja0205075

文献信息

• RNA Cleavage by a DNA Enzyme with Extended Chemical Functionality
  作者：Stephen W. Santoro、Gerald F. Joyce、Kandasamy Sakthivel、Svetlana Gramatikova、Carlos F. Barbas

  DOI：10.1021/ja993688s

  日期：2000.3.1

  imidazole-containing residues. The enzyme can be made to cleave RNAs of almost any sequence by simple alteration of the two substrate-recognition domains that surround the catalytic domain. The enzyme operates with multiple turnover in the presence of micromolar concentrations of Zn2+, exhibiting saturation kinetics and a catalytic rate of >1 min-1. The imidazole-containing DNA enzyme, one of the smallest known

  体外选择技术被应用于开发含有三个催化必需咪唑基团并催化 RNA 底物裂解的 DNA 酶。用于选择的核酸文库是通过聚合酶催化掺入 C5-咪唑功能化脱氧尿苷代替胸苷来构建的。化学合成用于定义仅由 12 个残基组成的最小化催化域。催化域形成紧凑的发夹结构，显示三个含咪唑的残基。通过简单改变围绕催化结构域的两个底物识别结构域，该酶可以切割几乎任何序列的 RNA。该酶在微摩尔浓度的 Zn2+ 存在下以多次周转运行，表现出饱和动力学和大于 1 min-1 的催化速率。含咪唑的 DNA 酶是已知最小的核酸酶之一，它将核酸酶的底物识别特性和蛋白质酶的化学功能结合在一个小分子中，但用途广泛且催化效率高。
• Toward an RNaseA Mimic:  A DNAzyme with Imidazoles and Cationic Amines
  作者：Leonard Lermer、Yoann Roupioz、Richard Ting、David M. Perrin

  DOI：10.1021/ja0205075

  日期：2002.8.1

  Site-specific RNA cleavage has received considerable attention over the years. Directed synthesis to append imidazoles or amines or both to oligonucleotides to target specific RNA cleavage represents an exciting avenue of research. However, to date catalysis by such synthetic constructs, particularly in terms of turnover, has been difficult to observe. This is the first report of a truly catalytic M2+-independent DNAzyme synthetically modified with imidazoles and cationic amines that would seem to mimic RNaseA. This work now demonstrates how synthetic organic chemistry, when merged with combinatorial selection, can result in a new class of DNAzymes that meets the ongoing synthetic challenges for developing relatively small biomimetic catalysts.