5-(1,2,3-Triazolyl)-2'-deoxyuridine | 1464808-86-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5-(1,2,3-Triazolyl)-2'-deoxyuridine
• 英文别名: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(2H-triazol-4-yl)pyrimidine-2,4-dione
• CAS: 1464808-86-3
• 化学式: C₁₁H₁₃N₅O₅
• 分子量: 295.255
• InChiKey: ATIKQLJUKDRSIU-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  141
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-乙炔-2-脱氧尿苷 在 copper(ll) sulfate pentahydrate 、 叠氮基三甲基硅烷 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以72%的产率得到5-(1,2,3-Triazolyl)-2'-deoxyuridine
  参考文献：
  名称：

  Fluorescent 5-Pyrimidine and 8-Purine Nucleosides Modified with an N-Unsubstituted 1,2,3-Triazol-4-yl Moiety

  摘要：

  The Cu(I)- or Ag(I)-catalyzed cycloaddition between 8-ethynyladenine or guanine nucleosides and TMSN 3 gave 8-(1-H-1,2,3-triazol-4-yl) nucleosides in good yields. On the other hand, reactions of 5-ethynyluracil or cytosine nucleosides with TMSN3 led to the chemoselective formation of triazoles via Cu(I)-catalyzed cycloaddition or vinyl azides via Ag(I)-catalyzed hydroazidation. These nucleosides with a minimalistic triazolyl modification showed excellent fluorescent properties with 8-(1-H-1,2,3-triazol-4-yl)-2'-deoxyadenosine (8-TrzdA), exhibiting a quantum yield of 44%. The 8-TrzdA 5'-triphosphate was incorporated into duplex DNA containing a one-nucleotide gap by DNA polymerase beta.

  DOI：

  10.1021/acs.joc.8b03135

文献信息

• One-pot approach to functional nucleosides possessing a fluorescent group using nucleobase-exchange reaction by thymidine phosphorylase
  作者：Akihiko Hatano、Masayuki Kurosu、Susumu Yonaha、Munehiro Okada、Sanae Uehara

  DOI：10.1039/c3ob41605d

  日期：——

  modified uracil and a deoxyribose to produce functionalized nucleosides catalyzed by thymidine phosphorylase derived from Escherichia coli. This enzyme mediates nucleobase-exchange reactions to convert unnatural nucleosides possessing a large functional group such as a fluorescent molecule, coumarin or pyrene, linked via an alkyl chain at the C5 position of uracil. 5-(Coumarin-7-oxyhex-5-yn)uracil (C4U)

  在本文中，我们描述了修饰的尿嘧啶和脱氧核糖之间的β-选择性偶联，以产生由大肠杆菌衍生的胸苷磷酸化酶催化的功能化核苷。该酶介导核碱基交换反应，以转化具有大功能基团（例如荧光分子）的非天然核苷，香豆素 或者 芘，通过烷基链在C5的位置连接尿嘧啶。5-（Coumarin-7-oxyhex-5-yn）尿嘧啶（C4U）在1.0 mM磷酸盐缓冲液pH 6.8中以40％DMSO浓度显示57.2％的转化率胸苷以C4U为碱基的非天然核苷。在使用5-（pyren-1-methyloxyhex-5-yn）尿嘧啶（P4U）作为底物的情况下，TP还可以催化反应以在DMSO浓度为50％（21.6％）时生成具有非常大的官能团的产物转换）。我们使用MF myPrest对绑定到TP活性位点的修饰尿嘧啶进行了对接模拟。底物的尿嘧啶部分与TP的活性位点结合，荧光部分与位于酶表面外侧的核碱基的C5位置相连。结果，庞大的荧光部分结合到尿嘧啶
• Fluorescent 5-Pyrimidine and 8-Purine Nucleosides Modified with an <i>N</i>-Unsubstituted 1,2,3-Triazol-4-yl Moiety
  作者：Zhiwei Wen、Paloma R. Tuttle、A. Hasan Howlader、Anna Vasilyeva、Laura Gonzalez、Antonija Tangar、Ruipeng Lei、Eduardo E. Laverde、Yuan Liu、Jaroslava Miksovska、Stanislaw F. Wnuk

  DOI：10.1021/acs.joc.8b03135

  日期：2019.3.15

  The Cu(I)- or Ag(I)-catalyzed cycloaddition between 8-ethynyladenine or guanine nucleosides and TMSN 3 gave 8-(1-H-1,2,3-triazol-4-yl) nucleosides in good yields. On the other hand, reactions of 5-ethynyluracil or cytosine nucleosides with TMSN3 led to the chemoselective formation of triazoles via Cu(I)-catalyzed cycloaddition or vinyl azides via Ag(I)-catalyzed hydroazidation. These nucleosides with a minimalistic triazolyl modification showed excellent fluorescent properties with 8-(1-H-1,2,3-triazol-4-yl)-2'-deoxyadenosine (8-TrzdA), exhibiting a quantum yield of 44%. The 8-TrzdA 5'-triphosphate was incorporated into duplex DNA containing a one-nucleotide gap by DNA polymerase beta.