5-nitro-2’-deoxyuridine-3’,5’-O-diacetate | 221343-94-8

• 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-nitro-2’-deoxyuridine-3’,5’-O-diacetate
• 英文别名: 3′,5′-di-O-acetyl-5-nitrodeoxyuridine；[(2R,3S,5R)-3-acetyloxy-5-(5-nitro-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl acetate
• CAS: 221343-94-8
• 化学式: C₁₃H₁₅N₃O₉
• 分子量: 357.277
• InChiKey: KCXIQGFJWYNXMW-HBNTYKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  157
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5-nitro-2’-deoxyuridine-3’,5’-O-diacetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以74%的产率得到1-[(2R,4S,5R)-4-羟基-5-(羟基甲基)四氢呋喃-2-基]-5-硝基嘧啶-2,4-二酮
  参考文献：
  名称：

  Nucleic Acid Related Compounds. 107. Efficient Nitration of Uracil Base and Nucleoside Derivatives¹

  摘要：

  DOI：

  10.1021/jo9822939
• 作为产物：
  描述：

  2-脱氧尿苷 在 吡啶 、 nitrosonium tetrafluoroborate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 5-nitro-2’-deoxyuridine-3’,5’-O-diacetate
  参考文献：
  名称：

  Phenyl-imidazolo-cytidine Analogues: Structure–Photophysical Activity Relationship and Ability To Detect Single DNA Mismatch

  摘要：

  To expand the arsenal of fluorescent cytidine analogues for the detection of genetic material, we synthesized para-substituted phenyl-imidazolo-cytidine ((Ph)ImC) analogues 5a-g and established a relationship between their structure and fluorescence properties. These analogues were more emissive than cytidine (λem 398-420 nm, Φ 0.009-0.687), and excellent correlation was found between Φ of 5a-g and σp(-) of the substituent on the phenyl-imidazolo moiety (R(2) = 0.94). Calculations suggested that the dominant tautomer of (Ph)ImC in methanol solution is identical to that of cytidine. DFT calculations of the stable tautomer of selected (Ph)ImC analogues suggested a relationship between the HOMO-LUMO gap and Φ and explained the loss of fluorescence in the nitro analogue. Incorporation of the CF3-(Ph)ImdC analogue into a DNA probe resulted in 6-fold fluorescence quenching of the former. A 17-fold reduction of fluorescence was observed for the G-matched duplex vs ODN(CF3-(Ph)ImdC), while for A-mismatched duplex, only a 2-fold decrease was observed. Furthermore, since the quantum yield of ODN(CF3-(Ph)ImdC):ODN(G) was reduced 17-fold vs that of a single strand, whereas that of ODN(CF3-(Ph)ImdC):ORN(G) was reduced only 3.8-fold, ODN(CF3-(Ph)ImdC) appears to be a DNA-selective probe. We conclude that the ODN(CF3-(Ph)ImdC) probe, exhibiting emission sensitivity upon single nucleotide replacement, may be potentially useful for DNA single nucleotide polymorphism (SNP) typing.

  DOI：

  10.1021/jo5011944

文献信息

• Fluorescence enhancement of oligodeoxynucleotides modified with green fluorescent protein chromophore mimics upon triplex formation
  作者：Takashi Kanamori、Akihiro Takamura、Nobuhiro Tago、Yoshiaki Masaki、Akihiro Ohkubo、Mitsuo Sekine、Kohji Seio

  DOI：10.1039/c6ob01278g

  日期：——

  5-positions of deoxyuridines, and subsequently, incorporated into the middle positions of oligodeoxynucleotides. These oligonucleotides were designed to form triplex DNA in order to encapsulate the GFP chromophores, mimicking GFP structures. Upon triplex formation, the embedded GFP chromophores exhibited fluorescence enhancement, suggesting the potential application of these fluorescent probes for the detection

  基于绿色荧光蛋白（GFP）的分子转子发色团连接到脱氧尿苷的5位，然后掺入到寡脱氧核苷酸的中间位置。设计这些寡核苷酸以形成三链体DNA，以封装GFP发色团，模仿GFP结构。在三链体形成后，嵌入的GFP生色团显示出荧光增强，表明这些荧光探针在核酸检测中的潜在应用。