3'-O-[(diisopropylamino)-(2-cyanoethoxy)phosphino]-5'-O-(4,4'-dimethoxytrityl)-N2-benzyl-8-oxo-7,8-dihydro-2'-deoxyguanosine | 1262310-97-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3'-O-[(diisopropylamino)-(2-cyanoethoxy)phosphino]-5'-O-(4,4'-dimethoxytrityl)-N2-benzyl-8-oxo-7,8-dihydro-2'-deoxyguanosine
• 英文别名: 3-[[(2R,3S,5R)-5-[2-(benzylamino)-6,8-dioxo-1,7-dihydropurin-9-yl]-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
• CAS: 1262310-97-3
• 化学式: C₄₇H₅₄N₇O₈P
• 分子量: 875.962
• InChiKey: ORBUIMZIAIEIAU-OBSXPSPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  63
• 可旋转键数：
  20
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  168
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2'-脱氧-8-(苯基甲氧基)-鸟苷 在 吡啶 、 盐酸 、 sodium cyanoborohydride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 3'-O-[(diisopropylamino)-(2-cyanoethoxy)phosphino]-5'-O-(4,4'-dimethoxytrityl)-N2-benzyl-8-oxo-7,8-dihydro-2'-deoxyguanosine
  参考文献：
  名称：

  Synthesis of N²-Alkyl-8-oxo-7,8-dihydro-2′-deoxyguanosine Derivatives and Effects of These Modifications on RNA Duplex Stability

  摘要：

  N-2-Alkyl analogues of 8-oxo-7,8-dihydro-2'-deoxyguanosine (OG) were synthesized (alkyl = propyl, benzyl) via reductive amination of the protected OG nucleoside and incorporated into various positions of an RNA strand. Thermal stability studies of duplexes containing A or C opposite a single modified base revealed only moderate destabilization. Both OG as well as its N-2-alkyl analogues can pair opposite A or C with nearly equal stability, potentially offering a new means of modulating RNA protein interactions in the minor vs major grooves.

  DOI：

  10.1021/jo102187y

文献信息

• Synthesis of <i>N</i>²-Alkyl-8-oxo-7,8-dihydro-2′-deoxyguanosine Derivatives and Effects of These Modifications on RNA Duplex Stability
  作者：Arunkumar Kannan、Cynthia J. Burrows

  DOI：10.1021/jo102187y

  日期：2011.1.21

  N-2-Alkyl analogues of 8-oxo-7,8-dihydro-2'-deoxyguanosine (OG) were synthesized (alkyl = propyl, benzyl) via reductive amination of the protected OG nucleoside and incorporated into various positions of an RNA strand. Thermal stability studies of duplexes containing A or C opposite a single modified base revealed only moderate destabilization. Both OG as well as its N-2-alkyl analogues can pair opposite A or C with nearly equal stability, potentially offering a new means of modulating RNA protein interactions in the minor vs major grooves.