2-amino-7-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-[6-[1-(pyren-1-ylmethyl)triazol-4-yl]hex-1-ynyl]-3H-pyrrolo[2,3-d]pyrimidin-4-one | 1203676-66-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 2-amino-7-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-[6-[1-(pyren-1-ylmethyl)triazol-4-yl]hex-1-ynyl]-3H-pyrrolo[2,3-d]pyrimidin-4-one
• CAS: 1203676-66-7
• 化学式: C₃₆H₃₃N₇O₄
• 分子量: 627.703
• InChiKey: CFGDABWWWMQWPZ-FRXPANAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  47
• 可旋转键数：
  9
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  153
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  7-deaza-7-(octa-1,7-diynyl)-2'-deoxyguanosine 、 1-(叠氮基甲基)芘 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 16.0h， 以83%的产率得到2-amino-7-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-[6-[1-(pyren-1-ylmethyl)triazol-4-yl]hex-1-ynyl]-3H-pyrrolo[2,3-d]pyrimidin-4-one
  参考文献：
  名称：

  在7-脱氮鸟嘌呤DNA上的“双击”反应：带有近端比尔牛装饰的带有分支侧链的核苷和寡核苷酸的合成和准分子荧光

  摘要：

  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

  DOI：

  10.1021/jo902300e

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
• 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.