2-azidodeoxyadenosine | 404839-80-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2-azidodeoxyadenosine
• 英文别名: 2-azido-9-(2-deoxy-β-D-erythro-pentofuranosyl)adenine；(2R,3S,5R)-5-(6-amino-2-azido-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol；(2R,3S,5R)-5-(6-amino-2-azidopurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
• CAS: 404839-80-1
• 化学式: C₁₀H₁₂N₈O₃
• 分子量: 292.257
• InChiKey: PLBOKIVEVSWRNR-KVQBGUIXSA-N

物化性质

• 熔点：
  181-182 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-azidodeoxyadenosine 在 亚磷酸二苯酯 、 碘 、 双(2-氧代-3-恶唑烷基)次磷酰氯 作用下， 以 吡啶 、 水 为溶剂， 反应 7.0h， 生成 2-azido-2'-deoxyadenyl(5'-3')thymidine
  参考文献：
  名称：

  Synthesis and properties of 2-azidodeoxyadenosine and its incorporation into oligodeoxynucleotides

  摘要：

  2-Azidodeoxyadenosine (7) was conveniently synthesized from deoxyguanosine (2) by use of a combined reagent of TMSN3-BuONO. The Structure Of the tautomer of the azido derivative was determined by H-1 NMR. Reaction of 7 with iPr(2)NP(OEt)(2) gave an intermediate 10 of the Staudinger reaction. Incorporation of 7 into a DNA 13mer resulted in a significant decrease of the T-m value of the DNA duplex upon hybridization with the complementary strand. The thermal stability was discussed based on the hydrogen bond energy and electrostatic repulsion. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02028-7
• 作为产物：
  描述：

  2'-脱氧鸟苷 在 4-二甲氨基吡啶 、 ammonium hydroxide 、 三甲基氯硅烷 、 亚硝酸丁酯 、 叠氮基三甲基硅烷 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 135.0h， 生成 2-azidodeoxyadenosine
  参考文献：
  名称：

  Synthesis and properties of 2-azidodeoxyadenosine and its incorporation into oligodeoxynucleotides

  摘要：

  2-Azidodeoxyadenosine (7) was conveniently synthesized from deoxyguanosine (2) by use of a combined reagent of TMSN3-BuONO. The Structure Of the tautomer of the azido derivative was determined by H-1 NMR. Reaction of 7 with iPr(2)NP(OEt)(2) gave an intermediate 10 of the Staudinger reaction. Incorporation of 7 into a DNA 13mer resulted in a significant decrease of the T-m value of the DNA duplex upon hybridization with the complementary strand. The thermal stability was discussed based on the hydrogen bond energy and electrostatic repulsion. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02028-7

文献信息

• Azido/Tetrazole Tautomerism in 2-Azidoadenineβ-D-Pentofuranonucleoside Derivatives
  作者：Thierry Lioux、Gilles Gosselin、Christophe Mathé

  DOI：10.1002/ejoc.200300274

  日期：2003.10

  and its 2′-deoxy-, 2′,3′-dideoxy- and 2′,3′-dideoxy-2′,3′-didehydro counterparts have been synthesized. All these compounds were obtained through the preparation of their 2-chloro precursors. These were converted into their 2-hydrazino derivatives, which upon treatment with sodium nitrate in acid medium gave the target nucleosides. The azido/tetrazole tautomerism observed in such nucleoside analogues

  已经合成了 2-叠氮腺嘌呤的 β-D-呋喃核苷衍生物及其 2'-脱氧-、2',3'-二脱氧-和 2',3'-二脱氧-2',3'-二脱氢对应物。所有这些化合物都是通过制备它们的 2-氯前体获得的。这些被转化为它们的 2-肼衍生物，在酸性介质中用硝酸钠处理后得到目标核苷。详细研究了在此类核苷类似物中观察到的叠氮基/四唑互变异构现象。还测试了这些化合物对 HIV 和 HBV 的活性，但没有显示出显着的抗病毒作用。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Detection of polynucleotides on nucleic acid arrays using azido-modified triphosphate nucleotide analogs
  申请人：Affymetrix, Inc.

  公开号：EP1686189A2

  公开（公告）日：2006-08-02

  Methods are provided for detecting hybridization of a polynucleotide to a nucleic acid array by chemically modifying the polynucleotide to contain a detectable label. According to one aspect of the present invention, a method is provided for detecting the presence of a mRNA in a nucleic acid sample, the method having the steps of providing a mRNA sample and azido modified nucleotides, hybridizing a primer to the mRNA, reversed transcribing the mRNA to provide azido modified DNA, followed by reacting the azido groups with a detectable label, hybridizing the labeled RNA to a nucleic acid array and detecting the presence of the mRNA. Still other methods are provided for detecting the presence or absence of a polynucleotide of interest on a nucleic acid array, the method having the steps of providing a nucleic acid sample comprising a polynucleotide; providing an enzyme to amplify the polynucleotide using an azido nucleotide derivative; amplifying said polynucleotide to provide azido labeled amplified nucleic acids; reacting the azido groups on said nucleic acids with a detectable label to provide labeled nucleic acids; hybridizing said amplified nucleic acids to a nucleic acid array; and detecting the presence or absence of said polynucleotide. Still other methods are presented for detecting polynucleotides on a nucleic acid array using ligases and terminal transferases to end label polynucleotides.

  本发明提供了通过化学修饰多核苷酸使其含有可检测标签来检测多核苷酸与核酸阵列杂交的方法。根据本发明的一个方面，提供了一种检测核酸样品中是否存在 mRNA 的方法，该方法包括以下步骤：提供 mRNA 样品和叠氮修饰的核苷酸，将引物与 mRNA 杂交，反转录 mRNA 以提供叠氮修饰的 DNA，然后使叠氮基团与可检测的标签反应，将标记的 RNA 与核酸阵列杂交并检测是否存在 mRNA。 还提供了其它方法，用于检测核酸阵列上是否存在感兴趣的多核苷酸，该方法的步骤包括：提供包含多核苷酸的核酸样品；提供使用叠氮核苷酸衍生物扩增多核苷酸的酶；扩增所述多核苷酸，以提供叠氮标记的扩增核酸；使所述核酸上的叠氮基团与可检测标记反应，以提供标记核酸；将所述扩增核酸杂交到核酸阵列上；以及检测所述多核苷酸的存在与否。 还提出了其他一些方法，用于检测核酸阵列上的多核苷酸，这些方法使用连接酶和末端转移酶对多核苷酸进行末端标记。
• Synthesis and Biological Evaluation of β-D-Pentofuranonucleoside Derivatives of 2-Azidoadenine and 6-Azidopurines
  作者：Christophe Mathé、Thierry Lioux、Gilles Gosselin

  DOI：10.1081/ncn-120021964

  日期：2003.10

  beta-D-pentofuranonucleoside derivatives of 2-azidoadenine and 6-azidopurines have been synthesized. The azido-tetrazolo tautomerism observed on such nucleoside analogues has been studied. The compounds were tested for their activity against HIV and HBV but they did not show significant antiviral effect.
• COMPOSITION AND VACCINE FOR TREATING PROSTATE CANCER
  申请人：CureVac AG

  公开号：EP3035954A1

  公开（公告）日：2016-06-29
• ARTIFICIAL NUCLEIC ACID MOLECULES
  申请人：CureVac AG

  公开号：EP3341482A1

  公开（公告）日：2018-07-04