1-(3'-deoxy-β-D-psicofuranosyl)uracil | 55697-37-5

• 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: 1-(3'-deoxy-β-D-psicofuranosyl)uracil
• 英文别名: Hydroxymethyldeoxyuridine；1-[(2S,4S,5R)-4-hydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 55697-37-5
• 化学式: C₁₀H₁₄N₂O₆
• 分子量: 258.231
• InChiKey: JBLMSVBXNOLRDE-PJKMHFRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(3'-deoxy-β-D-psicofuranosyl)uracil 在 palladium on activated charcoal 吡啶 、 sodium hydroxide 、 sodium azide 、 氢气 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 133.5h， 生成 (1S,3S,4S)-3-(methanesulfonyloxymethyl)-5-N-(4-monomethoxytrityl)-1-(uracil-1-yl)-5-aza-2-oxabicyclo[2.2.1]heptane
  参考文献：
  名称：

  新型双环核苷的合成仅限于S型构象，并在掺入寡脱氧核苷酸时对其杂交性质进行了初步评估。

  摘要：

  亚磷酰胺（1S，3R，4S）-3-（2-氰基乙氧基（二异丙基氨基）次膦氧甲基）-5-N-（4-单甲氧基三苯甲基）-1-（尿嘧啶-1-基）-5-氮杂-2-氧杂双环[ 2.2.1]由已知的1-（3'-脱氧-β-D-psicofuranosyl）尿嘧啶3合成新型双环核苷结构的庚烷18。对其结构进行构象分析，验证了其预期的S型呋喃糖构象，并且使用5'-> 3'定向的寡核苷酸合成方法，可将4'位置的仲氨基掺入寡核苷酸中，如先前对氨基磷酸酯所述。热变性研究表明，每种修饰对互补DNA和RNA的双链稳定性分别为-4.3和-2.7摄氏度，相当大的降低。

  DOI：

  10.1021/jo015602v
• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 1-(3'-deoxy-β-D-psicofuranosyl)uracil
  参考文献：
  名称：

  Ex-NovoandRevisumProcedures for the Preparation of C-1′ Branched Nucleosides

  摘要：

  C-1' acylated derivatives of 2'-deoxyuridine were obtained either by revising the existing procedures or by introducing a new methodology.

  DOI：

  10.1080/15257779908041524

文献信息

• Synthesis of 1′-phenazine-tethered psicofuranosyl oligonucleotides: The thermal stability and fluorescence properties of their duplexes and triplexes
  作者：D. Ossipov、J. Chattopadhyaya

  DOI：10.1016/s0040-4020(98)00237-3

  日期：1998.5

  corresponding 6′-O-DMTr protected 4′-phosphoramidite block 13 in three steps [7 → 9 (83%) → 11 (83%) → 13 (83%)], whereas compound 8 was used in the preparation of the modified solid support 14 in four steps [8 → 10 (28%) → 12 (70%) → 14]. Modified 9-mer ODNs 28 – 31 and 18-mer ODNs 22 – 25 were then assembled in a usual manner using automated solid-phase DNA synthesis protocol. The phenazine-tethered

  描述了在1-（3'-deoxypsicofuranosyl）尿嘧啶的C1'处与吩嗪（pzn）相连的修饰寡核苷酸（ODN）的合成，热稳定性以及其双链体和三链体的荧光性质。由1-（3'-脱氧吡喃呋喃糖基）尿嘧啶5 [ ]合成了关键中间体，其是通过吩嗪呋喃糖基尿嘧啶衍生物7和8与吩嗪1'连接的，该连接基由磷酸酯和两个亚甲基组成。化合物7转化成相应的6'- ø -DMTr保护的4'-亚磷酰胺块13中的三个步骤[7→9（83％）→11（83％）→13（83％）]，而化合物8在四个步骤[8→10（28％）→12（70％）→14 ]中，使用α-己内酰胺来制备改性的固体载体14。改性的9-mer寡核苷酸28 - 31和18-mer的寡核苷酸22 - 25然后在使用自动固相DNA合成协议通常的方式组装。吩嗪-拴系的九聚体（28 - 31），用于它们的能力，形成稳定的双链体与靶DNA-链（测试19 - 20）。测试了吩嗪系留的18聚体（22
• Synthesis and anti-HIV-1 activity of novel bicyclic nucleoside analogues restricted to an S-type conformation
  作者：Lisbet Kvrnø、Claus Nielsen、Richard H. Wightman

  DOI：10.1039/b004774k

  日期：——

  (1S,3R,4S)-3-Hydroxymethyl-1-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 9 and the corresponding cytosine derivative 10, nucleoside analogues with a novel bicyclic nucleoside structure 3, were synthesized in a few steps from the known 1-(3′-deoxy-β-D-psicofuranosyl)uracil 4. NOE experiments verified the bicyclic nucleosides to be restricted to the expected S-type furanose conformation while the nucleobase is in an anti-conformation. Both nucleosides proved to be devoid of anti-HIV activity in MT-4 cells, which further supports the hypothesis that conformational flexibility of the furanose ring in a nucleoside analogue is necessary to obtain both intracellular 5′-triphosphorylation and inhibition of HIV-1 reverse transcriptase.

  (1S,3R,4S)-3-羟甲基-1-(尿嘧啶-1-基)-2,5-二氧杂环[2.2.1]庚烷 9 和相应的胞嘧啶衍生物 10 是具有新型双环核苷结构 3 的核苷类似物，由已知的 1-(3′-脱氧-β-D-二十呋喃糖基)尿嘧啶 4 通过几个步骤合成。NOE 实验验证了双环核苷仅限于预期的 S 型呋喃糖构象，而核碱基则处于反构象。事实证明，这两种核苷在 MT-4 细胞中都没有抗 HIV 活性，这进一步证实了一个假设，即核苷类似物中呋喃糖环的构象灵活性是获得细胞内 5′-三磷酸化和抑制 HIV-1 逆转录酶的必要条件。
• In vivo labelling of polynucleotide sequences
  申请人：ENZO BIOCHEM, INC.

  公开号：EP0133473A2

  公开（公告）日：1985-02-27

  in vivo labelled polynucleotides, processes for in vivo labelling of polynucleotides, and detection methods and kits characterized by those labelled polynucleotides. In in vivo on biologically-labelled polynucleotides of this invention are useful in the detection of various analytes and in other laboratory, industrial and medical applications.

  体内标记的多核苷酸、体内标记多核苷酸的工艺以及以这些标记的多核苷酸为特征的检测方法和试剂盒。 本发明的体内生物标记多核苷酸可用于检测各种分析物以及其他实验室、工业和医疗应用。
• Vectors, cells and processes for pyrimidine deoxyribonucleosides production
  申请人：GLAXO GROUP LIMITED

  公开号：EP1806405A2

  公开（公告）日：2007-07-11

  Novel DNA constructs and host cells comprising the same are disclosed. DNA constructs comprise a transcription unit (eg. operon) comprising DNA sequences encoding for ribonucleotide reductase and thioredoxin or uridine kinase and/or a dCTP deaminase gene. In preferred embodiments the constructs comprising DNA sequences encoding for ribonucleotide reductase and thioredoxin further comprise DNA sequences encoding for thymidylate synthase and/or transcription units comprising sequences encoding for uridine kinase preferably together with dCTP deaminase. In particularly preferred embodiments, the host cells comprise constructs having all of the above characteristics wherein the host cell displays repressed or no uracil DNA glycosylase activity, This may be achieved by the removal of the host cell ung gere, Use of the host cells in the manufacture of pyrimidine deoxyribonucleotides eg. thymidine is also dislosed.

  本发明公开了新型 DNA 构建体和包含这些构建体的宿主细胞。DNA 构建体包括一个转录单元（如操作子），该单元由编码核糖核苷酸还原酶和硫氧还蛋白或尿苷激酶和/或 dCTP 脱氨酶基因的 DNA 序列组成。在优选的实施方案中，由编码核糖核苷酸还原酶和硫氧还蛋白的 DNA 序列组成的构建体还包括编码胸苷酸合成酶的 DNA 序列和/或由编码尿苷激酶的序列组成的转录单元（最好与 dCTP 脱氨酶一起）。在特别优选的实施方案中，宿主细胞包括具有上述所有特征的构建体，其中宿主细胞显示出被抑制的尿嘧啶 DNA 糖基化酶活性或没有尿嘧啶 DNA 糖基化酶活性。
• NOVEL ENDORIBONUCLEASE
  申请人：Takara Bio, Inc.

  公开号：EP1921138A1

  公开（公告）日：2008-05-14

  A polypeptide having a novel endoribonuclease activity; a nucleic acid encoding the polypeptide; recombinant DNA having the nucleic acid therein; a transformant transformed with the recombinant DNA; a process for producing the polypeptide comprising the steps of cultivating the transformant and collecting the polypeptide from the culture; a process for producing a digest of single-stranded RNA comprising the step of reacting the polypeptide with the single-stranded RNA; and a method for the digestion of single-stranded RNA.

  一种具有新型内切核酸酶活性的多肽；一种编码该多肽的核酸；一种具有该核酸的重组 DNA；一种用该重组 DNA 转化的转化体；一种生产多肽的工艺，包括培养转化体和从培养物中收集多肽的步骤；一种生产单链 RNA 消化物的工艺，包括使多肽与单链 RNA 反应的步骤；以及一种消化单链 RNA 的方法。