5-azido-2′-deoxyuridine | 137359-50-3

• 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-azido-2′-deoxyuridine
• 英文别名: 5-azido-2'-deoxyuridine；5-azido-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 137359-50-3
• 化学式: C₉H₁₁N₅O₅
• 分子量: 269.217
• InChiKey: YUCDFJIHSULTEQ-RRKCRQDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-azido-2′-deoxyuridine 在 溶剂黄146 作用下， 以 水 为溶剂， 以100%的产率得到1-(2-deoxy-β-D-erythro-pentofuranosyl)isodialuric acid
  参考文献：
  名称：

  Unraveling the Photochemistry of the 5-Azido-2′-deoxyuridine Photoaffinity Label

  摘要：

  UV irradiation of 5-azido-2'-deoxyuridine in water provides tip to seven products. All likely result from a pivotal azirene, formed by the intramolecular rearrangement of the initially formed nitrene, that undergoes nucleophilic addition at its C5 position. This study strongly suggests that only nucleophilic amino acid residues in close proximity are cross-linkable in photolabeling experiments by using the 5-azidouracil photophore.

  DOI：

  10.1021/jo901544a
• 作为产物：
  描述：

  溴脲苷 在 palladium 10% on activated carbon 、 甲酸铵 、 溶剂黄146 、 sodium nitrite 作用下， 以 甲醇 、 水 为溶剂， 反应 5.08h， 生成 5-azido-2′-deoxyuridine
  参考文献：
  名称：

  Highly Efficient and Facile Synthesis of 5-Azido-2′-Deoxyuridine

  摘要：

  Previously reported syntheses of the photoaffinity label 5-azido-2'-deoxyuridine are rather inefficient and involve the tedious preparation of a 5-nitro intermediate. To overcome these inconveniences, we have developed a new approach from the commercially available 5-bromo-2'-deoxyuridine nucleoside. Our synthetic route makes use of a benzylamination reduction sequence. Using this strategy, the 5-azido-2'-deoxyuridine photolabel is prepared in three steps and quantitative yields.

  DOI：

  10.1080/15257770.2010.487507

文献信息

• Strain Promoted Click Chemistry of 2- or 8-Azidopurine and 5-Azidopyrimidine Nucleosides and 8-Azidoadenosine Triphosphate with Cyclooctynes. Application to Living Cell Fluorescent Imaging
  作者：Jessica Zayas、Marie Annoual、Jayanta Kumar Das、Quentin Felty、Walter G. Gonzalez、Jaroslava Miksovska、Nima Sharifai、Akira Chiba、Stanislaw F. Wnuk

  DOI：10.1021/acs.bioconjchem.5b00300

  日期：2015.8.19

  Strain-promoted click chemistry of nucleosides and nucleotides with an azido group directly attached to the purine and pyrimidine rings with various cyclooctynes in aqueous solution at ambient temperature resulted in efficient formation (3 min to 3 h) of fluorescent, light-up, triazole products. The 2- and 8-azidoadenine nucleosides reacted with fused cyclopropyl cyclooctyne, dibenzylcyclooctyne, or

  在室温下，水溶液中各种环辛炔直接与嘌呤和嘧啶环连接的叠氮基基团的核苷和核苷酸的应变促进咔嗒化学反应，可有效形成（3分钟至3小时）荧光，发光，三唑产物。2-和8-叠氮腺嘌呤核苷与稠合的环丙基环辛炔，二苄基环辛炔或单氟环辛炔反应生成可被羟基，氨基，N官能化的点击产物-羟基琥珀酰亚胺或生物素部分。在不到5分钟的时间内，将5-叠氮胍和5-叠氮基2'-脱氧尿苷以定量收率类似地转化为类似的三唑产物。8-叠氮基-ATP在乙腈水溶液中定量提供三唑产物和稠合的环丙基环辛炔（3小时）。腺嘌呤2位或8位或尿嘧啶环5位的新型三唑加合物可诱导荧光特性，可用于MCF-7癌细胞的直接成像，而无需传统的荧光报告分子。三唑点击加合物的FLIM证明了其潜在活性，可用于动态测量和追踪单个活癌细胞内的信号事件。
• 5-azido-deoxyuridine compounds and method of synthesis of the same
  申请人：University of Wyoming

  公开号：US04672111A1

  公开（公告）日：1987-06-09

  5-azido-2-'-deoxyuridine nucleoside and nucleotide compounds and a method of producing them. The method involves reacting a 5'-deoxyuridine compound with nitrosonium tetrafluoroborate to produce a 5-nitro-deoxyuridine compound. The 5-nitro-deoxyuridine compound is reduced to a 5-amino-deoxyuridine compound in the presence of metallic zinc. The 5-amino-deoxyuridine compound is acidified and reacted with sodium nitrite to produce a 5-diazo-deoxyuridine compound. The diazo-deoxyuridine compound is then reacted with sodium azide to produce a 5-azido-deoxyuridine compound. The latter, in the monophosphate form, is further reacted with diphenylchlorophosphate to produce the photoactive triphosphate, 5-azido-2'-deoxyuridine-5'-triphosphate or 5-azido-dUTP. The photoactive compound, when added to DNA in an in vitro synthesis reaction, produces photoactive DNA.

  5-azido-2'-deoxyuridine核苷和核苷酸化合物及其生产方法。该方法涉及将5'-去氧尿嘧啶化合物与亚硝酸四氟硼酸盐反应，以产生5-硝基-去氧尿嘧啶化合物。在金属锌的存在下，将5-硝基-去氧尿嘧啶化合物还原为5-氨基-去氧尿嘧啶化合物。将5-氨基-去氧尿嘧啶化合物酸化并与亚硝酸钠反应，以产生5-重氮-去氧尿嘧啶化合物。然后，将重氮-去氧尿嘧啶化合物与叠氮化钠反应，以产生5-叠氮基-去氧尿嘧啶化合物。后者以单磷酸形式进一步与二苯基氯磷酸酯反应，以产生光活性三磷酸盐，5-叠氮基-2'-去氧尿嘧啶-5'-三磷酸盐或5-叠氮-dUTP。当将这种光活性化合物添加到体外合成反应中的DNA中时，将产生光活性DNA。
• Methods and compositions for labeling nucleic acids
  申请人：President and Fellows of Harvard College

  公开号：US10550422B2

  公开（公告）日：2020-02-04

  The present invention relates to methods for the labeling of nucleic acid polymers in vitro and in vivo. Certain methods are provided that include a [3+2] cycloaddition between a nucleotide analogue incorporated into a nucleic acid polymer and a reagent attached to a label. Other methods are provided that include a Staudinger ligation between a nucleotide analogue incorporated into a nucleic acid polymer and a reagent comprising a substituted triarylphosphine attached to a label. Such methods do not require fixation and denaturation and therefore can be applied to the labeling of nucleic acid polymers in living cells and in organisms. Also provided are methods for measuring cellular proliferation. In these methods, the amount of label incorporated into the DNA is measured as an indication of cellular proliferation. The methods of the invention can be used in a wide variety of applications including clinical diagnosis of diseases and disorders in which cellular proliferation is involved, toxicity assays, and as a tool for the study of chromosomes' ultrastructures.

  本发明涉及体外和体内标记核酸聚合物的方法。本发明提供的某些方法包括加入核酸聚合物的核苷酸类似物与附着在标签上的试剂之间的[3+2]环化反应。其他方法包括核酸聚合物中的核苷酸类似物与含有取代的三芳基膦的试剂之间的施陶丁格连接。这种方法不需要固定和变性，因此可用于活细胞和生物体内核酸聚合物的标记。此外，还提供了测量细胞增殖的方法。在这些方法中，结合到 DNA 中的标记量被测量为细胞增殖的指标。本发明的方法应用广泛，包括涉及细胞增殖的疾病和失调的临床诊断、毒性检测，以及作为研究染色体超微结构的工具。
• Mutated herpes simplex virus type 1 thymidine kinases and uses thereof
  申请人：——

  公开号：US20020146796A1

  公开（公告）日：2002-10-10

  The present invention provides new site-specific HSV-thymidine kinase mutants with improved nucleoside analog metabolizing activity due to low or no thymidine phosphorylation ability. Also provided is a method of killing target cells using such mutants combined with a prodrug.

  本发明提供了新的位点特异性 HSV 胸苷激酶突变体，这些突变体由于胸苷磷酸化能力低或没有胸苷磷酸化能力，因此具有更好的核苷类似物代谢活性。本发明还提供了一种利用这种突变体与原药结合杀死靶细胞的方法。
• [EN] 5-AZIDO DEOXYURIDINE COMPOUNDS AND METHOD OF SYNTHESIS OF THE SAME
  申请人：THE UNIVERSITY OF WYOMING

  公开号：WO1986006253A1

  公开（公告）日：1986-11-06

  (EN) 5-azido-2'-deoxyuridine nucleoside and nucleotide compounds and a method of producing them. The method involves reacting a 5'-deoxyuridine compound with nitrosonium tetrafluoroborate to produce a 5-nitro-deoxyuridine compound. The 5-nitro-deoxyuridine compound is reduced to a 5-amino-deoxyuridine compound in the presence of metallic zinc. The 5-amino-deoxyuridine compound is acidified and reacted with sodium nitrite to produce a 5-diazo-deoxyuridine compound. The diazo-deoxyuridine compound is then reacted with sodium azide to produce a 5-azido-deoxyuridine compound. The latter, in the monophosphate form, is further reacted with diphenylchlorophosphate to produce the photoactive triphosphate, 5-azido-2'-deoxyuridine-5'-triphosphate or 5-azido-dUTP. The photoactive compound, when added to DNA in an in vitro synthesis reaction, produces photoactive DNA.(FR) Composés de nucléosides et de nucléotides de 5-azido-2'-désoxyuridine et leur procédé de production. Le procédé comprend la réaction d'un composé de 5'-désoxyuridine avec du tétrafluoroborate nitrosé afin de produire un composé de 5-nitro-désoxyuridine. Le composé de 5-nitro-désoxyuridine est réduit à un composé de 5-amino-désoxyuridine en présence du zinc méallique. Le composé de 5-amino-désoxyuridine est acidifié et entre en réaction avec du nitrite de sodium pour produire un composé de 5-diazo-désoxyuridine. On fait ensuite réagir le composé de 5-diazo-désoxyuridine avec de l'azoture de sodium pour produire un composé de 5-azoture-désoxyuridine. On fait réagir ce dernier, sous sa forme monophosphate, avec du diphénylchlorophosphate pour produire un triphosphate photoactif, le 5-azoture-2'-désoxyuridine-5'-triphosphate ou 5-azoture-dVTP. Ajouté à l'ADN dans une réaction de synthèse $i(in vitro), ce composé photoactif produit de l'ADN photoactif.

  5-azido-2'-deoxyuridine 核苷和核苷酸化合物及其制备方法。该方法涉及将 5'-deoxyuridine 化合物与硝fonyl 四氟化硼反应，以制备 5-硝基-deoxyuridine 化合物。5-硝基-deoxyuridine 化合物在金属锌的条件下被还原为 5-氨基-deoxyuridine 化合物。5-氨基-deoxyuridine 化合物经酸化后与亚硝酸钠反应，生成 5-二⎦氮基-deoxyuridine 化合物。5-二⎦氮基-deoxyuridine 化合物与亚硝酸钠反应后，生成 5-azido-deoxyuridine 化合物。后者，以单磷酸形式存在，与二苯基磷酸化物反应，生成具有光活性的三磷酸，即 5-azido-2'-deoxyuridine-5'-triphosphate 或 5-azido-dVTP。将该光活性化合物与 DNA 在体外合成反应中结合，可生成光活性 DNA。