6-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-3-(octa-1,7-diynyl)-4H-pyrazolo[3,4-d]pyrimidin-4-one | 1152162-13-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 英文名称: 6-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-3-(octa-1,7-diynyl)-4H-pyrazolo[3,4-d]pyrimidin-4-one
• 英文别名: 7-(octa-1,7-diynyl)-8-aza-7-deaza-2'-deoxyguanosine；8-aza-7-deaza-7-(octa-1,7-diynyl)-2'-deoxyguanosine；6-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-octa-1,7-diynyl-5H-pyrazolo[3,4-d]pyrimidin-4-one
• CAS: 1152162-13-4
• 化学式: C₁₈H₂₁N₅O₄
• 分子量: 371.396
• InChiKey: FNVTWHIEXDMOLI-BFHYXJOUSA-N

物化性质

• 沸点：
  701.4±70.0 °C(predicted)
• 密度：
  1.45±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-3-(octa-1,7-diynyl)-4H-pyrazolo[3,4-d]pyrimidin-4-one 、 1,4-二甲苯二叠氮化 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 12.0h， 以40%的产率得到
  参考文献：
  名称：

  Cross-Linked DNA Generated by “Bis-click” Reactions with Bis-functional Azides: Site Independent Ligation of Oligonucleotides via Nucleobase Alkynyl Chains

  摘要：

  Template-free cross-linking of single-stranded DNA bearing octadiynyl side chains at the 7-position of 8-aza-7-deazapurine moieties with bisfunctional azides is reported employing a Cu(I)-catalyzed azide alkyne "bis-click" reaction. Bis-adducts were formed when the bis-azide:oligonucleotide ratio was 1:1; monofunctionalization occurred when the ratio was 15:1. Four-stranded DNA consisting of two cross-linked duplexes was obtained after hydridization. Cross-linked duplexes are as stable as individual duplexes when ligation was introduced at terminal positions; ligation at a central position led to a slight duplex destabilization.

  DOI：

  10.1021/jo101809w
• 作为产物：
  描述：

  1,7-辛二炔 、 6-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-3-iodo-4H-pyrazolo[3,4-d]pyrimidin-4-one 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以52%的产率得到6-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-3-(octa-1,7-diynyl)-4H-pyrazolo[3,4-d]pyrimidin-4-one
  参考文献：
  名称：

  8-Aza-7-脱氮鸟嘌呤核苷和具有辛二炔基侧链的寡核苷酸：合成，叠氮化物-炔烃“点击”反应的功能化和香豆素共轭物的核碱基特异性荧光猝灭†

  摘要：

  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

  DOI：

  10.1039/b822041g

文献信息

• Stepwise “Click” Chemistry for the Template Independent Construction of a Broad Variety of Cross-Linked Oligonucleotides: Influence of Linker Length, Position, and Linking Number on DNA Duplex Stability
  作者：Hai Xiong、Frank Seela

  DOI：10.1021/jo2004988

  日期：2011.7.15

  Cross-linked DNA was constructed by a "stepwise click" reaction using a bis-azide. The reaction is performed in the absence of a template, and a monofunctionalized oligonucleotide bearing an azido-function is formed as intermediate. For this, an excess of the bis-azide has to be used compared to the alkynylated oligonucleotide. The cross-linking can be carried out with any alkynylated DNA having a terminal triple bond at any position of the oligonucleotide, independent of chain length or sequence with identical or nonidentical chains. Short and long linkers with terminal triple bonds were introduced in the 7-position of 8-aza-7-deaza-2'-deoxyguanosine, (1 or 2), and the outcome of the "stepwise" click and the "bis-click" reaction was compared. The cross linked DNAs form cross linked duplexes when hybridized with single stranded complementary oligonucleotides. The stability of these cross linked duplexes is as high as respective individual duplexes when they were ligated at terminal positions with linkers of sufficient length. The stability decreases when the linkers are incorporated at central positions. The highest duplex stability was reached when two complementary cross-linked oligonucleotides were hybridized.
• 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.