4-amino-7-(2-deoxy-β-D-erythro-pentofuranosyl)-5-[3-{bis-((1-(pyren-1-ylmethyl)-1H-1,2,3-triazol-4-yl)methyl)amino}prop-1-yn-1-yl]-7H-pyrrolo[2,3-d]pyrimidine | 1352796-88-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 4-amino-7-(2-deoxy-β-D-erythro-pentofuranosyl)-5-[3-{bis-((1-(pyren-1-ylmethyl)-1H-1,2,3-triazol-4-yl)methyl)amino}prop-1-yn-1-yl]-7H-pyrrolo[2,3-d]pyrimidine
• 英文别名: (2R,3S,5R)-5-[4-amino-5-[3-[bis[[1-(pyren-1-ylmethyl)triazol-4-yl]methyl]amino]prop-1-ynyl]pyrrolo[2,3-d]pyrimidin-7-yl]-2-(hydroxymethyl)oxolan-3-ol
• CAS: 1352796-88-3
• 化学式: C₅₄H₄₃N₁₁O₃
• 分子量: 894.007
• InChiKey: WWQQCMHKFPPNJI-WEDPTRSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  68
• 可旋转键数：
  12
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  171
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  1-(叠氮基甲基)芘 、 7-(2-deoxy-β-D-erythro-pentofuranosyl)-5-{3-[di(prop-2-ynyl)amino]prop-1-ynyl}-7H-pyrrolo[2,3-d]pyrimidin-4-amine 在 copper(ll) sulfate pentahydrate 、 ascorbic acid sodium salt 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 16.0h， 以80%的产率得到4-amino-7-(2-deoxy-β-D-erythro-pentofuranosyl)-5-[3-{bis-((1-(pyren-1-ylmethyl)-1H-1,2,3-triazol-4-yl)methyl)amino}prop-1-yn-1-yl]-7H-pyrrolo[2,3-d]pyrimidine
  参考文献：
  名称：

  7-Deazapurine and 8-Aza-7-deazapurine Nucleoside and Oligonucleotide Pyrene “Click” Conjugates: Synthesis, Nucleobase Controlled Fluorescence Quenching, and Duplex Stability

  摘要：

  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.

  DOI：

  10.1021/jo202103q

文献信息

• 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.