8-[3-(6-dimethylaminonaphthalen-2-yl)-3-hydroxy-1-propyn-1-yl]-3'O,5'O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine | 936855-26-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 8-[3-(6-dimethylaminonaphthalen-2-yl)-3-hydroxy-1-propyn-1-yl]-3'O,5'O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine
• CAS: 936855-26-4
• 化学式: C₃₇H₅₄N₆O₅Si₂
• 分子量: 719.044
• InChiKey: BVPAHWVTEQWZJB-NIVBRBIASA-N

物化性质

• 沸点：
  797.7±70.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.71
• 重原子数：
  50.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  140.75
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  8-[3-(6-dimethylaminonaphthalen-2-yl)-3-hydroxy-1-propyn-1-yl]-3'O,5'O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine 在 platinum(IV) oxide 四丙基高钌酸铵 、 4 A molecular sieve 、 四丁基氟化铵 、 氢气 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 2N-(N,N-dimethylaminomethylidenyl)-8-(6-propionyl-2-dimethylaminonaphthalene)-2'-deoxyguanosine
  参考文献：
  名称：

  PRODAN-Conjugated DNA:  Synthesis and Photochemical Properties

  摘要：

  A solvatochromic fluorophore, PRODAN, has been used as a microenvironment-sensitive reporter. Based on the chemistry of PRODAN, we designed and synthesized four novel fluorescent nucleosides, X-PDN (X = U, C, A, and G), to which a PRODAN fluorophore was attached at pyrimidine C5 or purine C8. The fluorescent nucleosides sensitively varied the Stokes shift values depending on the orientational polarizability of the solvent. The X-PDN incorporated into DNA also changed the Stokes shift values depending on the DNA structure. In particular, the excitation spectrum of the X-PDN-containing duplex shifted to a longer wavelength and gave a smaller Stokes shift value when the base opposite X-PDN could form a Watson-Crick base pair with X-PDN. A lower energy excitation of X-PDN-containing DNA resulted in a strong fluorescence emission selective to the Watson-Crick pairing base. This unique photochemical character was applicable to the efficient typing of single-nucleotide polymorphisms of genes.

  DOI：

  10.1021/ja069156a
• 作为产物：
  描述：

  6-(二甲基氨基)-2-萘醛 在 copper(l) iodide 、 四(三苯基膦)钯 正丁基锂 、 sodium methylate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 8-[3-(6-dimethylaminonaphthalen-2-yl)-3-hydroxy-1-propyn-1-yl]-3'O,5'O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine
  参考文献：
  名称：

  PRODAN-Conjugated DNA:  Synthesis and Photochemical Properties

  摘要：

  A solvatochromic fluorophore, PRODAN, has been used as a microenvironment-sensitive reporter. Based on the chemistry of PRODAN, we designed and synthesized four novel fluorescent nucleosides, X-PDN (X = U, C, A, and G), to which a PRODAN fluorophore was attached at pyrimidine C5 or purine C8. The fluorescent nucleosides sensitively varied the Stokes shift values depending on the orientational polarizability of the solvent. The X-PDN incorporated into DNA also changed the Stokes shift values depending on the DNA structure. In particular, the excitation spectrum of the X-PDN-containing duplex shifted to a longer wavelength and gave a smaller Stokes shift value when the base opposite X-PDN could form a Watson-Crick base pair with X-PDN. A lower energy excitation of X-PDN-containing DNA resulted in a strong fluorescence emission selective to the Watson-Crick pairing base. This unique photochemical character was applicable to the efficient typing of single-nucleotide polymorphisms of genes.

  DOI：

  10.1021/ja069156a