4-N-acetyl-5-(6-propionyl-2-dimethylaminonaphthalene)-2'-deoxycytidine | 936855-23-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 4-N-acetyl-5-(6-propionyl-2-dimethylaminonaphthalene)-2'-deoxycytidine
• CAS: 936855-23-1
• 化学式: C₂₆H₃₀N₄O₆
• 分子量: 494.547
• InChiKey: JWYXDFFPMWJQLD-RBZQAINGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  133.99
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  4-N-acetyl-5-(6-propionyl-2-dimethylaminonaphthalene)-2'-deoxycytidine 在 四氮唑 作用下， 以 吡啶 、 乙腈 为溶剂， 反应 3.5h， 生成 4-N-acetyl-5-(6-propionyl-2-dimethylaminonaphthalene)-5'O-(4,4'-dimethoxytrityl)-2'-deoxycytidine 3'O-(2-cyanoethyl)-N,N-diisopropylphosphoramidite
  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-dimethylamino-2-(3-trimethylsilyl-1-hydroxy-2-propynyl)naphthalene 在 palladium on activated charcoal 、 copper(l) iodide 、 四(三苯基膦)钯 四丙基高钌酸铵 、 4 A molecular sieve 、 四丁基氟化铵 、 氨 、 氢气 、 sodium methylate 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 4-N-acetyl-5-(6-propionyl-2-dimethylaminonaphthalene)-2'-deoxycytidine
  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