5-(2-氰基乙烯基)-2'-脱氧尿苷 | 80173-35-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: 5-(2-氰基乙烯基)-2'-脱氧尿苷
• 中文别名: 1-氮杂二环[2.2.2]辛烷-3-硫醇
• 英文名称: 5-(cyanovinyl)-2'-deoxyuridine
• 英文别名: (E)-3-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]prop-2-enenitrile
• CAS: 80173-35-9
• 化学式: C₁₂H₁₃N₃O₅
• 分子量: 279.252
• InChiKey: USIRYNCTCFVRQR-HFVMFMDWSA-N

物化性质

• 密度：
  1.586±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(2-氰基乙烯基)-2'-脱氧尿苷 在 吡啶 、 四氮唑 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 17.0h， 生成
  参考文献：
  名称：

  R形DNA的光化学合成，朝向DNA重组和体外加工。

  摘要：

  DOI：

  10.1002/anie.200603161
• 作为产物：
  描述：

  2-deoxy-D-ribose 在 palladium diacetate 盐酸 、 ammonium hydroxide 、 copper(l) iodide 、 三乙胺 、 乙酰氯 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醚 、 乙腈 为溶剂， 反应 46.17h， 生成 5-(2-氰基乙烯基)-2'-脱氧尿苷
  参考文献：
  名称：

  Template-Directed DNA Photoligation via α-5-Cyanovinyldeoxyuridine

  摘要：

  We describe an efficient template-directed photoligation of oligodeoxynucleotides (ODNs) using alpha-5-cyanovinyldeoxyuridine (alpha U-C). An efficient photoligation was produced by photoirradiation of an ODN containing alpha U-C at the 3 ' end with an ODN containing thymine at the 5 ' end in the presence of a template ODN. This photoligation method is a new and efficient way to synthesize branched ODNs.

  DOI：

  10.1021/ol050709g

文献信息

• Pyridopyrimidine nucleotide compounds
  申请人：Teijin Limited

  公开号：US04965350A1

  公开（公告）日：1990-10-23

  Pyridopyrimidine nucleotide derivatives expressed by formula (I), which are fluorescent and capable of forming base pairing with guanine or adenine, and oligo- or polynucleotide which have at least one of these derivatives in their molecules or at their molecular terminals: ##STR1## wherein X.sub.1 and X.sub.1 respectively represent ##STR2## (in which n indicates an integer of 0, 1, 2, or 3; however, in no case X.sub.1 and Y.sub.1 both indicate n=O); Z.sub.1 indicates a hydrogen atom or ##STR3## (in which n indicates an integer of 1, 2, or 3); W.sub.1 indicates a hydrogen atom or a hydroxyl group. As for R.sub.1 and R.sub.2, in case where R.sub.1 is an amino group or halogen, R.sub.2 indicates a single bond between the carbon atom at the 7-position and the nitrogen atom at the 8-position, and in case where R.sub.2 is a hydrogen atom or an lower alkyl group, R.sub.1 indicates a carbonyl bond ##STR4## formed with the carbon atom at the 7-position.

  式(I)所表示的吡啶嘧啶核苷酸衍生物是荧光的，并能够与鸟嘌呤或腺嘌呤形成碱基配对，而具有这些衍生物之一的寡聚核苷酸或多聚核苷酸在其分子中或其分子末端至少有一个这些衍生物：其中X.sub.1和X.sub.1分别表示##STR2##（其中n表示0、1、2或3的整数；但在任何情况下，X.sub.1和Y.sub.1都不表示n=0）；Z.sub.1表示氢原子或##STR3##（其中n表示1、2或3的整数）；W.sub.1表示氢原子或羟基。至于R.sub.1和R.sub.2，在R.sub.1为氨基或卤素的情况下，R.sub.2表示7位碳原子和8位氮原子之间的单键，而在R.sub.2为氢原子或较低烷基的情况下，R.sub.1表示与7位碳原子形成的羰基键##STR4##。
• Combining Wittig Olefination with Photoassisted Domino Reaction To Distinguish 5-Formylcytosine from 5-Formyluracil
  作者：Qian Zhou、Kun Li、Ling-Ling Li、Kang-Kang Yu、Hong Zhang、Lei Shi、Hao Chen、Xiao-Qi Yu

  DOI：10.1021/acs.analchem.9b02499

  日期：2019.8.6

  5fC from 5-formyluracil to achieve higher accuracy is particularly difficult because the latter one is more reactive. Herein, we reported a phosphorus ylide, YC–CN, and introduced a triple domino reaction to fluorescently switch on 5fC with excellent selectivity, which also enable us to quantify 5fC mutations induced by γ-irradiation. This Wittig-initiated covalent labeling strategy provide a novel

  鉴于5-甲酰基胞嘧啶（5fC）的重要表观遗传功能，开发5fC定量检测方法是一个长期存在的问题。在这一点上，如何区分5fC与5-甲酰尿嘧啶以实现更高的准确度特别困难，因为后者更具反应性。在本文中，我们报道了磷叶立德YC-CN，并引入了三重多米诺反应，以优异的选择性荧光打开5fC，这也使我们能够量化由γ辐射诱导的5fC突变。这种由维蒂希（Wittig）启动的共价标记策略为5fC的定性和定量检测提供了一种新颖的策略。
• Nucleosides and Nucleotides. 131. Synthesis and Properties of Oligonucleotides Containing 5-Formyl-2'-deoxyuridine.
  作者：Akira ONO、Tomoko OKAMOTO、Michiyo INADA、Hiroshi NARA、Akira MATSUDA

  DOI：10.1248/cpb.42.2231

  日期：——

  corresponding to 1 was not detected clearly by HPLC analysis of a nucleoside mixture obtained by complete hydrolysis of I-1. Therefore, the oligonucleotide I-1 was treated with cyanomethylene-triphenylphosphorane to give an oligonucleotide containing (E) and (Z)-5-(2-cyanovinyl)-2'- deoxyuridine, which was then hydrolyzed, and the newly generated nucleosides were detected by HPLC analysis. The Tm of

  将胸苷转化为5-甲酰基-2'-脱氧尿苷（1），将其掺入寡核苷酸5'd（GGAGA1CTCC）3'（I-1）和5'd（GCTGC1GCGAAAGCTG）3'（II-1）。为避免副反应和降解，必须使用新开发的保护基N，N-二-（3,5-二氯苯基）乙二胺保护1的甲酰基。在用于寡核苷酸的酶完全消化的条件下，化合物1是不稳定的，因此通过HPLC分析通过I-1的完全水解获得的核苷混合物，没有清楚地检测到对应于1的峰。因此，将寡核苷酸I-1用氰基亚甲基三苯基膦处理，得到含有（E）和（Z）-5-（2-氰基乙烯基）-2'-脱氧尿苷的寡核苷酸，然后将其水解，并通过HPLC分析检测新产生的核苷。在包含0.01 M磷酸钠（pH 7.0）的缓冲液中，自我互补寡核苷酸I-1（40°C）的Tm高于亲本寡核苷酸5'd（GGAGATCTCC）3'（31°C）的Tm。 ）和0.1 M NaCl。在模板引物系统[引物，5'd（
• Structural requirements of olefinic 5-substituted deoxyuridines for antiherpes activity
  作者：John Goodchild、Roderick A. Porter、Robert H. Raper、Iain S. Sim、Roger M. Upton、Julie Viney、Harry J. Wadsworth

  DOI：10.1021/jm00363a009

  日期：1983.9

  A number of structurally related 5-substituted pyrimidine 2'-deoxyribonucleosides were synthesized and tested for antiviral activity against herpes simplex virus type 1 (HSV-1) in cell culture. A minimum inhibitory concentration was determined for each compound, and from a comparison of these values a number of conclusions were drawn with regard to those molecular features that enhance or reduce antiviral activity. Optimum inhibition of HSV-1 in cell culture occurred when the 5-substituent was unsaturated and conjugated with the pyrimidine ring, was not longer than four carbon atoms in length, had E stereochemistry, and included a hydrophobic, electronegative function but did not contain a branching point. Such features are contained in (E)-5-(2-bromovinyl)-2'-deoxyuridine, which was the most active of the compounds described.
• PYRIDOPYRIMIDINE NUCLEOTIDE DERIVATIVES
  申请人：TEIJIN LIMITED

  公开号：EP0235301B1

  公开（公告）日：1992-07-22