3',5'-bis-O-tert-butyldimethylsilyl-2'-deoxy-6-N-{2-[(1,3-diaza-3-methyl-2-oxophenoxazin-9-yl)oxy]ethyl}-2-aminoadenosine | 1609081-32-4

• 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: 3',5'-bis-O-tert-butyldimethylsilyl-2'-deoxy-6-N-{2-[(1,3-diaza-3-methyl-2-oxophenoxazin-9-yl)oxy]ethyl}-2-aminoadenosine
• CAS: 1609081-32-4
• 化学式: C₃₅H₅₃N₉O₆Si₂
• 分子量: 752.034
• InChiKey: QQQODPYWSLEAPJ-SKBVVQJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.54
• 重原子数：
  52.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  174.72
• 氢给体数：
  3.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  3',5'-bis-O-tert-butyldimethylsilyl-2'-deoxy-6-N-{2-[(1,3-diaza-3-methyl-2-oxophenoxazin-9-yl)oxy]ethyl}-2-aminoadenosine 在 吡啶 、 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 N-(9-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-6-((2-((3-methyl-2-oxo-2,10-dihydro-3H-benzo[b]pyrimido[4,5-e][1,4]oxazin-9-yl)oxy)ethyl)amino)-9H-purin-2-yl)-2-phenoxyacetamide
  参考文献：
  名称：

  2,6-Diaminopurine nucleoside derivative of 9-ethyloxy-2-oxo-1,3-diazaphenoxazine (2-amino-Adap) for recognition of 8-oxo-dG in DNA

  摘要：

  8-Oxo-2'-deoxyguanosine (8-oxo-dG) is a nucleoside resulting from oxidative damage and is known to be mutagenic. 8-Oxo-dG has been related to aging and diseases, including neurological disorders and cancer. Recently, we reported that a fluorescent nucleoside derivative, adenosine-1,3-diazaphenoxazine (Adap), forms a stable base pair with 8-oxo-dG in DNA with accompanying efficient quenching. In this study, a new Adap derivative having an additional 2-amino group on the adenosine moiety (2-amino-Adap) was designed with the anticipation of additional hydrogen bonding with the 8-oxo group of 8-oxo-dG. The properties of the ODN containing 2-amino-Adap were evaluated by measuring thermal stability and fluorescence quenching. In contrast to the previously designed Adap, the base-pairing and fluorescence quenching properties of 2-amino-Adap varied depending on the ODN sequence, and there was no clear indication of an additional hydrogen bond with 8-oxo-dG. Instead, the base pairing of 2-amino-Adap with dG was significantly destabilized compared with that of Adap with dG, resulting in improved selectivity for 8-oxo-dG in the human telomere DNA sequence. Thus, the telomere-targeting ODN probe containing 2-amino-Adap displayed selective, sensitive and quantitative detection of 8-oxo-dG in the human telomere DNA sequence in a light-up detection system using SYBR Green. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2014.01.024
• 作为产物：
  描述：

  3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine 在 4-二甲氨基吡啶 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 丙醇 、 二氯甲烷 为溶剂， 反应 60.0h， 生成 3',5'-bis-O-tert-butyldimethylsilyl-2'-deoxy-6-N-{2-[(1,3-diaza-3-methyl-2-oxophenoxazin-9-yl)oxy]ethyl}-2-aminoadenosine
  参考文献：
  名称：

  2,6-Diaminopurine nucleoside derivative of 9-ethyloxy-2-oxo-1,3-diazaphenoxazine (2-amino-Adap) for recognition of 8-oxo-dG in DNA

  摘要：

  8-Oxo-2'-deoxyguanosine (8-oxo-dG) is a nucleoside resulting from oxidative damage and is known to be mutagenic. 8-Oxo-dG has been related to aging and diseases, including neurological disorders and cancer. Recently, we reported that a fluorescent nucleoside derivative, adenosine-1,3-diazaphenoxazine (Adap), forms a stable base pair with 8-oxo-dG in DNA with accompanying efficient quenching. In this study, a new Adap derivative having an additional 2-amino group on the adenosine moiety (2-amino-Adap) was designed with the anticipation of additional hydrogen bonding with the 8-oxo group of 8-oxo-dG. The properties of the ODN containing 2-amino-Adap were evaluated by measuring thermal stability and fluorescence quenching. In contrast to the previously designed Adap, the base-pairing and fluorescence quenching properties of 2-amino-Adap varied depending on the ODN sequence, and there was no clear indication of an additional hydrogen bond with 8-oxo-dG. Instead, the base pairing of 2-amino-Adap with dG was significantly destabilized compared with that of Adap with dG, resulting in improved selectivity for 8-oxo-dG in the human telomere DNA sequence. Thus, the telomere-targeting ODN probe containing 2-amino-Adap displayed selective, sensitive and quantitative detection of 8-oxo-dG in the human telomere DNA sequence in a light-up detection system using SYBR Green. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2014.01.024