N-2-(9-Fluorenylmethoxycarbonyl)-2'-deoxyguanosin-8-yl>-2-(acetylamino)fluorene | 153875-49-1

• 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: N-2-(9-Fluorenylmethoxycarbonyl)-2'-deoxyguanosin-8-yl>-2-(acetylamino)fluorene
• 英文别名: 9H-fluoren-9-ylmethyl N-[8-[acetyl(9H-fluoren-2-yl)amino]-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-oxo-1H-purin-2-yl]carbamate
• CAS: 153875-49-1
• 化学式: C₄₀H₃₄N₆O₇
• 分子量: 710.746
• InChiKey: DWOQOILQMNRVBA-LBFZIJHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  53
• 可旋转键数：
  8
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  168
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-2-(9-Fluorenylmethoxycarbonyl)-2'-deoxyguanosin-8-yl>-2-(acetylamino)fluorene 在 二氯乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以81%的产率得到N-2-(9-Fluorenylmethoxycarbonyl)guanin-8-yl>-2-(acetylamino)fluorene
  参考文献：
  名称：

  Synthesis of Oligonucleotides Containing Site-specific Carcinogen Adducts. Preparation of the 2-Cyanoethyl N,N-Diisopropylphosphoramidite of N-(2'-Deoxyguanosin-8-yl)-2-(acetylamino)fluorene with Fmoc as the Base-Protecting Group

  摘要：

  A 9-fluorenylmethoxycarbonyl (Fmoc) group was used to protect the exocyclic amine on the modified guanine of N-(2'-deoxyguanosin-8-yl)-2-(acetylamino)fluorene (dG-C-8-AAF) so that oligonucleotides containing a site-specific AAF adduct could be prepared. Reaction of Fmoc-Cl with dG-C-8-AAF gave N-[N-2-(9-fluorenylmethoxycarbonyl)-2'-deoxyguanosin-8-yl]-2-(acetylamino)fluorene (N2-Fmoc-dG- and N-[O-6-(9-fluorenylmethoxycarbonyl)-2'-deoxyguanosin-8-yl]-2-(acetylamino)fluorene (O-6-Fmoc-dG-C-8-AAF). The 5'-OH of N-2-FmoodG-C-8-AAF was protected using 4,4'-dimethoxrytrityl chloride to yield 5/-Dh4T-N-2-Fmoc-dG-C-8-AAF which was then reacted with 2-cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite to obtain the corresponding phosphoramidite. The phosphoramidites of Fmoc-protected dA, dC and dG were also prepared similarly. The stability of Fmoc-protected C-8-AAF-modified deoxyguanosine was studied under different conditions to establish the utility of the prepared phosphoramidite in solid-phase DNA synthesis.

  DOI：

  10.1021/jo00082a011
• 作为产物：
  描述：

  N-[2-氨基-9-[(4S,5R)-4-羟基-5-(羟基甲基)四氢呋喃-2-基]-6-氧代-3H-嘌呤-8-基]-N-(9H-芴-2-基)乙酰胺 在 吡啶 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 N-2-(9-Fluorenylmethoxycarbonyl)-2'-deoxyguanosin-8-yl>-2-(acetylamino)fluorene
  参考文献：
  名称：

  Synthesis of Oligonucleotides Containing Site-specific Carcinogen Adducts. Preparation of the 2-Cyanoethyl N,N-Diisopropylphosphoramidite of N-(2'-Deoxyguanosin-8-yl)-2-(acetylamino)fluorene with Fmoc as the Base-Protecting Group

  摘要：

  A 9-fluorenylmethoxycarbonyl (Fmoc) group was used to protect the exocyclic amine on the modified guanine of N-(2'-deoxyguanosin-8-yl)-2-(acetylamino)fluorene (dG-C-8-AAF) so that oligonucleotides containing a site-specific AAF adduct could be prepared. Reaction of Fmoc-Cl with dG-C-8-AAF gave N-[N-2-(9-fluorenylmethoxycarbonyl)-2'-deoxyguanosin-8-yl]-2-(acetylamino)fluorene (N2-Fmoc-dG- and N-[O-6-(9-fluorenylmethoxycarbonyl)-2'-deoxyguanosin-8-yl]-2-(acetylamino)fluorene (O-6-Fmoc-dG-C-8-AAF). The 5'-OH of N-2-FmoodG-C-8-AAF was protected using 4,4'-dimethoxrytrityl chloride to yield 5/-Dh4T-N-2-Fmoc-dG-C-8-AAF which was then reacted with 2-cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite to obtain the corresponding phosphoramidite. The phosphoramidites of Fmoc-protected dA, dC and dG were also prepared similarly. The stability of Fmoc-protected C-8-AAF-modified deoxyguanosine was studied under different conditions to establish the utility of the prepared phosphoramidite in solid-phase DNA synthesis.

  DOI：

  10.1021/jo00082a011

文献信息

• Synthesis of Oligonucleotides Containing Site-specific Carcinogen Adducts. Preparation of the 2-Cyanoethyl N,N-Diisopropylphosphoramidite of N-(2'-Deoxyguanosin-8-yl)-2-(acetylamino)fluorene with Fmoc as the Base-Protecting Group
  作者：Yuanzhong Zhou、Stanislav Chladek、Louis J. Romano

  DOI：10.1021/jo00082a011

  日期：1994.2

  A 9-fluorenylmethoxycarbonyl (Fmoc) group was used to protect the exocyclic amine on the modified guanine of N-(2'-deoxyguanosin-8-yl)-2-(acetylamino)fluorene (dG-C-8-AAF) so that oligonucleotides containing a site-specific AAF adduct could be prepared. Reaction of Fmoc-Cl with dG-C-8-AAF gave N-[N-2-(9-fluorenylmethoxycarbonyl)-2'-deoxyguanosin-8-yl]-2-(acetylamino)fluorene (N2-Fmoc-dG- and N-[O-6-(9-fluorenylmethoxycarbonyl)-2'-deoxyguanosin-8-yl]-2-(acetylamino)fluorene (O-6-Fmoc-dG-C-8-AAF). The 5'-OH of N-2-FmoodG-C-8-AAF was protected using 4,4'-dimethoxrytrityl chloride to yield 5/-Dh4T-N-2-Fmoc-dG-C-8-AAF which was then reacted with 2-cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite to obtain the corresponding phosphoramidite. The phosphoramidites of Fmoc-protected dA, dC and dG were also prepared similarly. The stability of Fmoc-protected C-8-AAF-modified deoxyguanosine was studied under different conditions to establish the utility of the prepared phosphoramidite in solid-phase DNA synthesis.