5-溴-2'-脱氧尿苷 5'-单磷酸酯 | 6666-38-2

• 物质功能分类: 化学试剂 - 有机试剂 - 膦酸酯/膦酸盐
• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 中文名称: 5-溴-2'-脱氧尿苷 5'-单磷酸酯
• 中文别名: 5-溴-2'-脱氧尿苷5'-单磷酸酯
• 英文名称: 5Br-dUMP
• 英文别名: 5-bromo-2'-deoxyuridine-5'-monophosphate；5-bromo-2'-deoxyuridine 5'-phosphate；5-bromodesoxyuridine monophosphate；5-bromo-2'-deoxy-[5']uridylic acid；5-bromo-2'-deoxyuridine 5'-monophosphate；5-bromodeoxyuridine monophosphate；[(2R,3S,5R)-5-(5-bromo-2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate
• CAS: 6666-38-2
• 化学式: C₉H₁₂BrN₂O₈P
• 分子量: 387.081
• InChiKey: LHLHVDBXXZVYJT-RRKCRQDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  146
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-溴-2'-脱氧尿苷 5'-单磷酸酯 在 Mycobacterium tuberculosis 、 5’-三磷酸腺苷 作用下， 生成 5Br-dUDP
  参考文献：
  名称：

  胸苷和胸苷5'-O-单磷酸酯类似物可作为结核分枝杆菌胸苷酸激酶的抑制剂。

  摘要：

  评估了一系列2'，3'-和5-修饰的胸苷类似物对结核分枝杆菌胸苷单磷酸激酶（TMPKmt）的亲和力。几种非磷酸化类似物的亲和力与其磷酸化同类物的亲和力处于相同的数量级。考虑到与磷酸化化合物有关的药物传递问题，这些“游离”核苷似乎在寻找TMPKmt抑制剂作为新型抗结核药方面更具前景。

  DOI：

  10.1016/s0960-894x(03)00643-7
• 作为产物：
  描述：

  溴脲苷 在 1,8-双二甲氨基萘 、 三氯氧磷 、 水 作用下， 反应 0.4h， 以58%的产率得到5-溴-2'-脱氧尿苷 5'-单磷酸酯
  参考文献：
  名称：

  Fully Automated Continuous Meso-flow Synthesis of 5′-Nucleotides and Deoxynucleotides

  摘要：

  The first continuous meso-flow synthesis of natural and non-natural 5'-nucleotides and deoxynucleotides is described, representing a significant advance over the corresponding in-flask method. By means of this meso-flow technique, a synthesis with time consumption and high-energy consumption becomes facile to generate products with great efficiency. An abbreviated duration, satisfactory output, and mild reaction conditions are expected to be realized under the present procedure.

  DOI：

  10.1021/op5002066

文献信息

• OLIGONUCLEOTIDE
  申请人：Kyowa Hakko Kirin Co., Ltd.

  公开号：US20150376611A1

  公开（公告）日：2015-12-31

  The present invention provides an oligonucleotide having improved affinity for AGO2, and the like. The oligonucleotide has a nucleotide residue or a nucleoside residue represented by formula (I) wherein X 1 is an oxygen atom or the like, R 1 is formula (IIA) (wherein R 5A is halogen or the like, and R 6A is a hydrogen atom or the like) or formula (IVA) (wherein Y 3A is a nitrogen atom or the like, and Y 4A is CH or the like), or the like, R 2 is a hydrogen atom, hydroxy, halogen, or optionally substituted lower alkoxy, and R 3 is a hydrogen atom or the like} at the 5′ end thereof, and the nucleotide residue or the nucleoside residue binds to an adjacent nucleotide residue through the oxygen atom at position 3.

  本发明提供了一种具有改善对AGO2亲和力的寡核苷酸等。该寡核苷酸在其5'端具有由式(I)表示的核苷酸残基或核苷酸残基其中X 1 是氧原子或类似物，R 1 是式(IIA)（其中R 5A 是卤素或类似物，而R 6A 是氢原子或类似物）或式(IVA)（其中Y 3A 是氮原子或类似物，而Y 4A 是CH或类似物），或类似物，R 2 是氢原子、羟基、卤素或可选择地取代的较低烷氧基，而R 3 是氢原子或类似物}，并且该核苷酸残基或核苷酸残基通过位于位置3的氧原子与相邻核苷酸残基结合。
• Novel Antiviral C5-Substituted Pyrimidine Acyclic Nucleoside Phosphonates Selected as Human Thymidylate Kinase Substrates
  作者：Dimitri Topalis、Ugo Pradère、Vincent Roy、Christophe Caillat、Ahmed Azzouzi、Julie Broggi、Robert Snoeck、Graciela Andrei、Jay Lin、Staffan Eriksson、Julie A. C. Alexandre、Chahrazade El-Amri、Dominique Deville-Bonne、Philippe Meyer、Jan Balzarini、Luigi A. Agrofoglio

  DOI：10.1021/jm1011462

  日期：2011.1.13

  Acyclic nucleoside phosphonates (ANPs) are at the cornerstone of DNA virus and retrovirus therapies. They reach their target, the viral DNA polymerase, after two phosphorylation steps catalyzed by cellular kinases. New pyrimidine ANPs have been synthesized with unsaturated acyclic side chains (prop-2-enyl-, but-2-enyl-, pent-2-enyl-) and different substituents at the C5 position of the uracil nucleobase

  无环核苷膦酸酯（ANP）是DNA病毒和逆转录病毒疗法的基石。在细胞激酶催化的两个磷酸化步骤后，它们达到了目标，即病毒DNA聚合酶。已经合成了新的嘧啶ANP，其具有不饱和的无环侧链（丙-2-烯基，丁-2-烯基，戊-2-烯基）和在尿嘧啶核碱基的C5位置具有不同的取代基。丁-2-烯基系列9d和9e中的几个衍生物，带有（E）但没有带有（Z）构型是人胸苷单磷酸（TMP）激酶的有效底物，而不是尿苷单磷酸-胞嘧啶单磷酸（UMP-CMP）激酶的有效底物，这与西多福韦相反。人TMP激酶已成功与磷酸化的（E）-胸苷-丁-2-烯基膦酸酯9e和ADP形成复合物结晶。的双-新戊酰氧基（POM）酯（ë） - 9D和（ë） - 9E的合成和体外显示出发挥活性抗疱疹病毒（IC 50 = 3μM）和体外抗水痘带状疱疹病毒（IC 50 = 0.19μM），与之相对应的无效（Z）衍生产品。因此，它们的抗病毒活性与其充当胸苷酸激酶底物的能力有关。
• OLIGONUCLEOTIDE HAVING NON-NATURAL NUCLEOTIDE AT 5'-TERMINAL THEREOF
  申请人：Kyowa Hakko Kirin Co., Ltd.

  公开号：US20170354673A1

  公开（公告）日：2017-12-14

  An oligonucleotide having a nucleotide residue or a nucleoside residue represented by formula (I) wherein X 1 is an oxygen atom or the like, R 1 is formula (IIA) (wherein R 5A is halogen or the like, and R 6A is a hydrogen atom or the like), formula (IVA) (wherein Y 3A is a nitrogen atom or the like, and Y 4A is CH or the like), or the like, R 2 is a hydrogen atom, hydroxy, halogen, or optionally substituted lower alkoxy, and R 3 is a hydrogen atom or the like, or formula (VI) (wherein n2 is 1, 2 or 3)} at the 5′ end thereof, wherein the nucleotide residue or the nucleoside residue binds to an adjacent nucleotide residue through the oxygen atom at position 3, is provided.

  具有由式(I)表示的核苷酸残基或核苷酸残基的寡核苷酸其中X1是氧原子或类似物，R1是式(IIA)（其中R5A是卤素或类似物，而R6A是氢原子或类似物），式(IVA)（其中Y3A是氮原子或类似物，而Y4A是CH或类似物），或类似物，R2是氢原子，羟基，卤素，或可选择地取代的较低烷氧基，而R3是氢原子或类似物，或式(VI)（其中n2为1、2或3）}在其5'端，其中核苷酸残基或核苷酸残基通过位于位置3的氧原子与相邻核苷酸残基结合。
• Sugar moiety labeled nucleotide, and an oligo- or polynucleotide, and other compositions comprising such sugar moiety labeled nucleotides
  申请人：Enzo Life Sciences, Inc. c/o Enzo Biochem, Inc.

  公开号：US07220854B1

  公开（公告）日：2007-05-22

  The present invention provides a nucleotide having the formula, wherein PM is a phosphate moiety, SM is a ribose or a deoxyribose sugar moiety, and BASE is a pyrimidine, purine or 7-deazapurine moiety. PM is attached to SM at a position independently selected from the 2′, 3′, and 5′ positions of SM when the nucleotide is a ribonucleotide, and at a position independently selected from the 3′ and 5′ positions when the nucleotide is a deoxyribonucleotide. BASE is attached to the 1′ position of SM from the N1 position when BASE is a pyrimidine, or the N9 position when BASE is a purine or 7-deazapurine. Sig is a detectable moiety covalently attached to SM directly or through a linkage group. Also provided are an oligo- or polynucleotide comprising at least one such sugar moiety labeled nucleotide, and other compositions including those wherein a polypeptide is terminal ligated or attached to the oligo- or polynucleotide. The sugar moiety labeled nucleotide, and the oligo- or polynucleotides and other compositions comprising such nucleotides, are useful as diagnostic tools for detecting analytes and as therapeutic agents.

  本发明提供了一种具有以下式子的核苷酸，其中PM是磷酸基团，SM是核糖或去氧核糖糖基团，BASE是嘧啶、嘌呤或7-去氮嘧啶基团。当核苷酸为核糖核苷酸时，PM在SM的2'、3'和5'位置中的任一位置与SM连接；当核苷酸为去氧核糖核苷酸时，PM在SM的3'和5'位置中的任一位置与SM连接。当BASE为嘧啶时，BASE与SM的1'位置从N1位置连接；当BASE为嘌呤或7-去氮嘧啶时，BASE与SM的1'位置从N9位置连接。Sig是可检测的基团，直接或通过连接基团与SM共价连接。还提供了至少包含一种这样的糖基团标记核苷酸的寡核苷酸或多核苷酸，以及其他包括末端连接或连接到寡核苷酸或多核苷酸的多肽的组合物。这种糖基团标记核苷酸，以及包含这种核苷酸的寡核苷酸或多核苷酸和其他组合物，可用作检测分析物的诊断工具和治疗剂。
• Nucleic acid sequencing processes using non-radioactive detectable modified or labeled nucleotides or nucleotide analogs, and other processes for nucleic acid detection and chromosomal characterization using such non-radioactive detectable modified or labeled nucleotides or nucleotide analogs
  申请人：Enzo Biochem, Inc.

  公开号：US08097405B1

  公开（公告）日：2012-01-17

  A process for determining the sequence of nucleic acids of interest employs nucleotides or nucleotide analogs that have been made detectable by non-radioactive modifying or labeling. Such nucleotides or nucleotide analogs are modified on the sugar moieties, the phosphate moieties or the base moieties, including base analogs. Modified nucleotide analogs can be attached to or coupled to or incorporated into DNA or RNA. The modified or labeled nucleotides or nucleotide analogs are also useful in processes for detecting the presence of nucleic acids of interest and for characterizing chromosomal sequences. Detection processes using the modified or labeled nucleotides or nucleotide analogs extend to the use of a gel for separating or resolving hybrids formed between non-radioactively labeled oligonucleotides or polynucleotides and such nucleic acids of interest.

  一种确定感兴趣的核酸序列的过程，采用已经通过非放射性修饰或标记制成可检测的核苷酸或核苷酸类似物。这些核苷酸或核苷酸类似物在糖基团、磷酸基团或碱基团（包括碱基类似物）上进行了修饰。修饰的核苷酸类似物可以连接到、耦合到或并入DNA或RNA中。修饰或标记的核苷酸或核苷酸类似物也可用于检测感兴趣的核酸的存在和表征染色体序列的过程。使用修饰或标记的核苷酸或核苷酸类似物的检测过程还包括使用凝胶分离或分辨非放射性标记的寡核苷酸或多核苷酸与这些感兴趣的核酸形成的杂交体。