7-deaza-7-(octa-1,7-diynyl)-2'-deoxyguanosine | 1002322-66-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 7-deaza-7-(octa-1,7-diynyl)-2'-deoxyguanosine
• 英文别名: 7-deaza-7-(octa-1,7-diynyl)-2'-dG；2-amino-7-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-octa-1,7-diynyl-3H-pyrrolo[2,3-d]pyrimidin-4-one
• CAS: 1002322-66-8
• 化学式: C₁₉H₂₂N₄O₄
• 分子量: 370.408
• InChiKey: VKGBIACLOLJIEY-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  122
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-deaza-7-(octa-1,7-diynyl)-2'-deoxyguanosine 在 磷酸三甲酯 、 三正丁胺 、 1,8-双二甲氨基萘 、 三丁基焦磷酸铵 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以2%的产率得到7-deaza-7-(octa-1,7-diynyl)-2'-deoxyguanosine-5'-triphosphate
  参考文献：
  名称：

  CLICK CHEMISTRY FOR THE PRODUCTION OF REPORTER MOLECULES

  摘要：

  公开号：

  EP2089343B1
• 作为产物：
  描述：

  1-(trimethylsilyl)-1,7-octadiyne 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 氨 、 水 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 7-deaza-7-(octa-1,7-diynyl)-2'-deoxyguanosine
  参考文献：
  名称：

  CLICK CHEMISTRY FOR THE PRODUCTION OF REPORTER MOLECULES

  摘要：

  公开号：

  EP2089343B1

文献信息

• “Double Click” Reaction on 7-Deazaguanine DNA: Synthesis and Excimer Fluorescence of Nucleosides and Oligonucleotides with Branched Side Chains Decorated with Proximal Pyrenes
  作者：Frank Seela、Sachin A. Ingale

  DOI：10.1021/jo902300e

  日期：2010.1.15

  phosphoramidite 7. This was employed in solid-phase synthesis of a series of oligonucleotides. Tm measurements demonstrate that a covalently attached tripropargylamine side chain increases duplex stability. Both terminal triple bonds of nucleoside 2 and corresponding oligonucleotides were functionalized by the Cu(I)-mediated 1,3-dipolar cycloaddition “double click reaction” with 1-azidomethyl pyrene 3, decorating

  通过Sonogashira交叉偶联反应，从相应的7-碘核苷1b合成了在侧链中含有两个末端三键的7-三炔丙基胺-7-deaza-2'-脱氧鸟苷（2）。将其在2-氨基处用异丁酰基残基保护，得到被保护的中间体5。然后，将化合物5转化为5'- O - DMT衍生物6，其经磷酸化反应得到亚磷酰胺7。这被用于一系列寡核苷酸的固相合成中。Ť米测量表明，共价连接的三炔丙基胺侧链增加了双链体的稳定性。核苷2和相应寡核苷酸的两个末端三键都通过与1-叠氮甲基pyr 3的Cu（I）介导的1,3-偶极环加成“双击反应”功能化，用两个近端pyr修饰侧链。带有两个近端pyr的单体三炔丙基胺核苷（4）显示出很强的准分子荧光，而含有4个近端的ss-寡核苷酸才不是。当互补链未修饰时，对于ds-寡核苷酸也观察到了这一点。然而，当每条链含有两个连接到三炔丙基胺部分的each残基时，在两条链中均带有pyr残基的双链DNA显示出强的
• 8-Aza-7-deazaguanine nucleosides and oligonucleotides with octadiynyl side chains: synthesis, functionalization by the azide-alkyne ‘click’ reaction and nucleobase specific fluorescence quenching of coumarin dye conjugates
  作者：Frank Seela、Hai Xiong、Peter Leonard、Simone Budow

  DOI：10.1039/b822041g

  日期：——

  chains have steric freedom in duplex DNA. Nucleoside 2d as well as 2d-containing oligonucleotides were conjugated to the non-fluorescent 3-azido-7-hydroxycoumarin 15 by the Huisgen-Meldal-Sharpless ‘click’ reaction. Pyrazolo[3,4-d]pyrimidine nucleoside conjugate 16 shows a much higher fluorescence intensity than that of the corresponding pyrrolo[2,3-d]pyrimidine derivative 17. The quenching in the dye conjugate

  通过固相合成制备了 掺入8-氮杂-7-脱氮杂-2'-脱氧鸟苷（2d）的7-（八-1,7-二炔基）衍生物的寡核苷酸。通过Sonogashira交叉偶联反应引入2d的侧链，并合成亚磷酰胺（3a，3b）。与包含未官能化的8-氮杂7-脱氮基2'-脱氧鸟苷（2a）的双链体相比，含2d的双链体更加稳定，这表明这些侧链在双链体DNA中具有空间自由度。将核苷2d和含2d的寡核苷酸偶联到非荧光的3-azido-7-羟基香豆素上15，由Huisgen-Meldal-Sharpless做出的“点击”反应。吡唑并[3，4- d ]嘧啶核苷共轭物16显示出比相应的吡咯并[2，3- d ]嘧啶衍生物17更高的荧光强度。发现在染料缀合物17中的猝灭在单体缀合物阶段比在单链或双链DNA中更强。提出了核碱基-染料接触复合物，当核碱基是堆叠的一部分时，其在单体状态下比在DNA链中更有利。具有笨重的染料缀合物的侧链很好地容纳在
• Synthesis of Modified DNA by PCR with Alkyne-Bearing Purines Followed by a Click Reaction
  作者：Philipp M. E. Gramlich、Christian T. Wirges、Johannes Gierlich、Thomas Carell

  DOI：10.1021/ol7026015

  日期：2008.1.1

  Alkyne-bearing deazapurine triphosphates were prepared and successfully incorporated into DNA using the polymerase chain reaction (PCR). The obtained alkyne-labeled DNA was successfully used in a click reaction with galactose azide.

  制备了含炔的三氮杂嘌呤三磷酸，并使用聚合酶链反应（PCR）成功地将其掺入了DNA中。所获得的炔烃标记的DNA已成功用于与半乳糖叠氮化物的点击反应。
• Nucleosides And Oligonucleotides With Diynyl Side Chains: The Huisgen-Sharpless Cycloaddition “Click Reaction” Performed On Dna And Their Constituents
  作者：Frank Seela、Venkata Ramana Sirivolu

  DOI：10.1080/15257770701490308

  日期：2007.11.26

  Phosphoramidite building blocks related to the four canonical DNA constituents and oligonucleotides with octadiynyl side chains (5b-8b) or dipropargyl ether residues (5c) were synthesized. Nucleosides and oligonucleotides were functionalized at the terminal triple bonds employing the Huisgen-Sharpless cycloaddition '' click reaction ''.
• 7-Deazapurine and 8-Aza-7-deazapurine Nucleoside and Oligonucleotide Pyrene “Click” Conjugates: Synthesis, Nucleobase Controlled Fluorescence Quenching, and Duplex Stability
  作者：Sachin A. Ingale、Suresh S. Pujari、Venkata Ramana Sirivolu、Ping Ding、Hai Xiong、Hui Mei、Frank Seela

  DOI：10.1021/jo202103q

  日期：2012.1.6

  7-Deazapurine and 8-aza-7-deazapurine nucleosides related to dA and dG bearing 7-octadiynyl or 7-tripropargylamine side chains as well as corresponding oligonucleotides were synthesized. "Click" conjugation with 1-azidomethyl pyrene (10) resulted in fluorescent derivatives. Octadiynyl conjugates show only monomer fluorescence, while the proximal alignment of pyrene residues in the tripropargylamine derivatives causes excimer emission. 8-Aza-7-deazapurine pyrene 'click" conjugates exhibit fluorescence emission much higher than that of 7-deazapurine derivatives. They are quenched by intramolecular charge transfer between the nucleobase and the dye. Oligonucleotide single strands decorated with two "double clicked" pyrenes show weak or no excimer fluorescence. However, when duplexes carry proximal pyrenes in complementary strands, strong excimer fluorescence is observed. A single replacement of a canonical nucleoside by a pyrene conjugate stabilizes the duplex substantially, most likely by stacking interactions: 6-12 degrees C for duplexes with a modified "adenine" base and 2-6 degrees C for a modified "guanine" base. The favorable photophysical properties of 8-aza-7-deazapurine pyrene conjugates improve the utility of pyrene fluorescence reporters in oligonucleotide sensing as these nucleoside conjugates are not affected by nucleobase induced quenching.