N2-phenoxyacetyl-3'-TBDMS-2'-deoxyguanosine | 1323344-95-1

• 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: N2-phenoxyacetyl-3'-TBDMS-2'-deoxyguanosine
• 英文别名: 3’-O-(tert-butyldimethylsilyl)-N²-phenoxyacetyl-2’-deoxyguanosine
• CAS: 1323344-95-1
• 化学式: C₂₄H₃₃N₅O₆Si
• 分子量: 515.641
• InChiKey: BMEQGPBJEBPKJP-YQVWRLOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 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：
  0.5
• 拓扑面积：
  140.59
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  N2-phenoxyacetyl-3'-TBDMS-2'-deoxyguanosine 在 4-二甲氨基吡啶 、 triethylamine tris(hydrogen fluoride) 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 5'-BODIPY-FL-2'-deoxyguanosine
  参考文献：
  名称：

  BODIPY-modified 2′-deoxyguanosine as a novel tool to detect DNA damages

  摘要：

  BODIPY-modified 2'-deoxyguanosine was synthesized for use as a detection reagent for genotoxic compounds. BODIPY-FL is a well known fluorescence reagent whose fluorescent light emission diminishes near a guanine base by a photo-induced electron transfer process. We attached BODIPY-FI to the 5' position of the deoxyribose moiety of 2'-deoxyguanosine. Although this compound has low fluorescence activity, when depurination by the action of alkylating reagents and dG oxidation by singlet oxygen occurred, the emission of strong fluorescence was observed. BODIPY-dG was found, therefore, to be a very useful tool for selectively detecting DNA damaging activity particularly in natural environmental extracts. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.084
• 作为产物：
  描述：

  3’,5’-O-bis(tert-butydimethylsilyl)-N²-phenoxyacetyl-2’-deoxyguanosine 在 四丁基氟化铵 、 溶剂黄146 作用下， 生成 N2-phenoxyacetyl-3'-TBDMS-2'-deoxyguanosine
  参考文献：
  名称：

  BODIPY-modified 2′-deoxyguanosine as a novel tool to detect DNA damages

  摘要：

  BODIPY-modified 2'-deoxyguanosine was synthesized for use as a detection reagent for genotoxic compounds. BODIPY-FL is a well known fluorescence reagent whose fluorescent light emission diminishes near a guanine base by a photo-induced electron transfer process. We attached BODIPY-FI to the 5' position of the deoxyribose moiety of 2'-deoxyguanosine. Although this compound has low fluorescence activity, when depurination by the action of alkylating reagents and dG oxidation by singlet oxygen occurred, the emission of strong fluorescence was observed. BODIPY-dG was found, therefore, to be a very useful tool for selectively detecting DNA damaging activity particularly in natural environmental extracts. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.084

文献信息

• Synthesis, Characterization, and Repair of a Flexible<i>O</i>⁶-2′-Deoxyguanosine-alkylene-<i>O</i>⁶-2′-deoxyguanosine Intrastrand Cross-Link
  作者：Derek K. O'Flaherty、Christopher J. Wilds

  DOI：10.1002/chem.201501103

  日期：2015.7.13

  Oligonucleotides tethered by an alkylene linkage between the O6‐atoms of two consecutive 2′‐deoxyguanosines, which lack a phosphodiester linkage between these residues, have been synthesized as a model system of intrastrand cross‐linked (IaCL) DNA. UV thermal denaturation studies of duplexes formed between these butylene‐ and heptylene‐linked oligonucleotides with their complementary DNA sequences revealed about

  作为两个链内交联（IaCL）DNA的模型系统，已经合成了通过两个连续的2'-脱氧鸟苷的O 6原子之间的亚烷基键束缚的寡核苷酸，这些残基之间没有磷酸二酯键。这些丁烯和庚烯连接的寡核苷酸及其互补的DNA序列之间形成的双链体的UV热变性研究表明，相对于未修饰的双链体，其稳定性降低了约20°C。模型IaCL双链体的圆二色性光谱显示了B型DNA的特征，表明病变引起的总体扰动最小。研究了包含IaCL模型的双链体作为O 6的底物来自人和大肠杆菌（Ada-C和OGT）的-烷基鸟嘌呤DNA烷基转移酶（AGT）蛋白。发现人类AGT可以修复两种IaCL双链体，对庚烯和丁烯类似物的修复效率更高，这进一步增加了我们对该蛋白可以修复的底物的了解。