1-(2-deoxy-beta-D-ribofuranosyl)-4-propynyl-2-nitropyrrole | 940949-71-3

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 1-(2-deoxy-beta-D-ribofuranosyl)-4-propynyl-2-nitropyrrole
• 英文别名: 1-(2-deoxy-β-D-ribofuranosyl)-4-propynyl-2-nitropyrrole；(2R,3S,5R)-2-(hydroxymethyl)-5-(2-nitro-4-prop-1-ynylpyrrol-1-yl)oxolan-3-ol
• CAS: 940949-71-3
• 化学式: C₁₂H₁₄N₂O₅
• 分子量: 266.254
• InChiKey: SQWKRJVUIZJVRP-HOSYDEDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(2-deoxy-β-D-ribofuranosyl)-2-nitropyrrole 在 bis-triphenylphosphine-palladium(II) chloride 、 N-碘代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 1.5h， 生成 1-(2-deoxy-beta-D-ribofuranosyl)-4-propynyl-2-nitropyrrole
  参考文献：
  名称：

  Nucleic acid base analogs with quenching and fluorescent activities and applications thereof

  摘要：

  本发明的目的是提供淬灭或荧光核酸碱基类似物及其应用。本发明的淬灭剂具有由式I表示的2-硝基吡咯结构：[Formula 1]（在式I中，R1和R2是从以下组成的组中独立选择的基团：核糖和去氧核糖；氢、羟基和SH基团、卤素；取代或未取代的具有2到10个碳原子的烷基、烯基和炔基基团；一个或多个含氮或硫的五元杂环环、一个或多个含氮或硫的六元杂环环以及一个或多个融合的杂环环；糖、糖链、氨基酸和肽；以及通过连接物连接的荧光分子）。

  公开号：

  US09285319B2

文献信息

• A New Unnatural Base Pair System between Fluorophore and Quencher Base Analogues for Nucleic Acid-Based Imaging Technology
  作者：Michiko Kimoto、Tsuneo Mitsui、Rie Yamashige、Akira Sato、Shigeyuki Yokoyama、Ichiro Hirao

  DOI：10.1021/ja1072383

  日期：2010.11.3

  selectivity in PCR amplification. Thus, this new unnatural base pair system would be suitable for detection methods of target nucleic acid sequences, and here we demonstrated the applications of the Dss-Pn and Dss-Px pairs as molecular beacons and in real-time PCR. The genetic alphabet expansion system with the replicable, unnatural fluorophore-quencher base pair will be a useful tool for sensing and diagnostic

  在开发用于扩展遗传字母表的正交额外碱基对的过程中，我们在荧光团和猝灭剂核碱基类似物之间创建了新的、非自然的碱基对。我们发现核碱基类似物 2-硝基吡咯（用 Pn 表示）及其 4-取代基，如 2-nitro-4-propynylpyrrole (Px) 和 4-[3-(6-aminohexanamido)-1-propynyl] -2-硝基吡咯 (NH(2)-hx-Px)，作为荧光猝灭剂。Pn 和 Px 碱基与其配对伙伴 7-(2,2'-bithien-5-yl)imidazo[4,5-b] 吡啶 (Dss) 特异性配对，后者具有强荧光。因此，这些非天然的 Dss-Pn 和 Dss-Px 碱基对起到报告基因-猝灭剂碱基对的作用，并通过聚合酶反应作为与天然 AT 和 GC 对结合的第三个碱基对互补整合到 DNA 中。由于静态接触淬火，Pn 和 Px 猝灭剂碱基通过 DNA 双链体中的非自然碱基配对显着降低了
• METHOD FOR REPLICATING NUCLEIC ACIDS AND NOVEL UNNATURAL BASE PAIRS
  申请人：Hirao Ichiro

  公开号：US20100036111A1

  公开（公告）日：2010-02-11

  The present invention relates to a method for nucleic acid replication and novel artificial base pairs. The method of the present invention for nucleic acid replication is characterized in that a deoxyribonucleoside 5′-triphosphate, in which the hydroxyl group of phosphoric acid at the γ-position is substituted with a group selected from the group consisting of an amino group, a methylamino group, a dimethylamino group, a mercapto group and a fluoro group, is used as a substrate during replication reaction. The novel artificial base pairs of the present invention are characterized in that 7-(2-thienyl)-imidazo[4,5-b]pyridine (Ds) or an analog thereof forms a base pair with pyrrole-2-carbaldehyde (Pa) or an analog thereof.

  本发明涉及一种核酸复制方法和新型人工碱基对。本发明的核酸复制方法的特征在于，在复制反应过程中使用一种脱氧核苷酸5'-三磷酸作为底物，其中磷酸γ-位置的羟基被从以下群组中选择的一种群组所取代，所述群组包括氨基、甲基氨基、二甲基氨基、巯基和氟基。本发明的新型人工碱基对的特征在于，7-(2-噻吩基)-咪唑并[4,5-b]吡啶（Ds）或其类似物与吡咯-2-甲醛（Pa）或其类似物形成一对碱基。
• Method for nucleic acid replication and novel artificial base pairs
  申请人：Riken

  公开号：US08030478B2

  公开（公告）日：2011-10-04

  The present invention relates to a method for nucleic acid replication and novel artificial base pairs. The method of the present invention for nucleic acid replication is characterized in that a deoxyribonucleoside 5′-triphosphate, in which the hydroxyl group of phosphoric acid at the γ-position is substituted with a group selected from the group consisting of an amino group, a methylamino group, a dimethylamino group, a mercapto group and a fluoro group, is used as a substrate during replication reaction. The novel artificial base pairs of the present invention are characterized in that 7-(2-thienyl)-imidazo[4,5-b]pyridine (Ds) or an analog thereof forms a base pair with pyrrole-2-carbaldehyde (Pa) or an analog thereof.

  本发明涉及一种核酸复制方法和新型人工碱基对。本发明的核酸复制方法的特征在于，在复制反应中使用一种脱氧核糖核苷酸5'-三磷酸，其中磷酸的γ-位置的羟基被从以下群组中选出的一种基团替代，所述群组包括氨基、甲基氨基、二甲基氨基、巯基和氟基。本发明的新型人工碱基对的特征在于，7-(2-噻吩基)-咪唑并[4,5-b]吡啶（Ds）或其类似物与吡咯-2-甲醛（Pa）或其类似物形成碱基对。
• NUCLEIC ACID FRAGMENT BINDING TO TARGET PROTEIN
  申请人：RIKEN

  公开号：US20150119254A1

  公开（公告）日：2015-04-30

  An object of the present invention is to develop and provide a method for efficiently producing a nucleic acid aptamer, particularly, a DNA aptamer, having higher specificity and binding activity against a target substance than those of nucleic acid aptamers obtained by conventional methods. The present invention provides a transcribable or replicable nucleic acid aptamer comprising a natural nucleotide and a non-natural nucleotide having an artificial base-pairable artificial base. The present invention also provides a method for sequencing a non-natural nucleotide-containing single-stranded nucleic acid molecule selected from a single-stranded nucleic acid library.

  本发明的目的是开发并提供一种有效生产核酸适配体的方法，特别是DNA适配体，其对目标物质具有比传统方法获得的核酸适配体更高的特异性和结合活性。本发明提供了一种可转录或可复制的核酸适配体，其包含一种自然核苷酸和一种非自然核苷酸，后者具有人工可配对人造碱基。本发明还提供了一种从单链核酸库中选择的含有非自然核苷酸的单链核酸分子的测序方法。
• NUCLEIC ACID BASE ANALOGS WITH QUENCHING AND FLUORESCENT ACTIVITIES AND APPLICATIONS THEREOF
  申请人：Hirao Ichiro

  公开号：US20130122506A1

  公开（公告）日：2013-05-16

  It is an object of the present invention to provide quenching or fluorescent nucleic acid base analogs and applications thereof. The quencher of the present invention has a 2-nitropyrrole structure represented by Formula I: [Formula 1] (in Formula I, R 1 and R 2 are groups independently selected from the group consisting of: ribose and deoxyribose; hydrogen, hydroxyl and SH groups, and halogens; substituted or unsubstituted alkyl, alkenyl, and alkynyl groups each having 2 to 10 carbon atoms; one or more five-membered heterocyclic rings, one or more six-membered heterocyclic rings, and one or more fused heterocyclic rings, these heterocylic rings containing nitrogen or sulfur, and one or more aromatic rings; sugars, sugar chains, amino acids, and peptides; and fluorescent molecules linked via linkers).

  本发明的目的是提供熄灭或荧光核酸碱基类似物及其应用。本发明的熄灭剂具有由公式I表示的2-硝基吡咯结构：[公式1]（在公式I中，R1和R2是从以下组成的组中独立选择的基团：核糖和脱氧核糖；氢、羟基和SH基团以及卤素；取代或未取代的烷基、烯基和炔基基团，每个基团具有2至10个碳原子；一个或多个含氮或硫的五元杂环、六元杂环和融合杂环，这些杂环中含有一个或多个芳香环；糖、糖链、氨基酸和肽；以及通过连接基连接的荧光分子）。