N2-propyl-8-oxo-7,8-dihydro-2'-deoxyguanosine | 1246662-16-7

• 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-propyl-8-oxo-7,8-dihydro-2'-deoxyguanosine
• 英文别名: 9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-(propylamino)-1,7-dihydropurine-6,8-dione
• CAS: 1246662-16-7
• 化学式: C₁₃H₁₉N₅O₅
• 分子量: 325.324
• InChiKey: YEXMHGBLBPLDNQ-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  136
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N2-propyl-8-oxo-7,8-dihydro-2'-deoxyguanosine 在 吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 3'-O-[(diisopropylamino)-(2-cyanoethoxy)phosphino]-5'-O-(4,4'-dimethoxytrityl)-N2-propyl-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
• 作为产物：
  描述：

  2'-脱氧鸟苷 在 盐酸 、 溴 、 sodium 、 sodium cyanoborohydride 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 N2-propyl-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

• METHODS AND COMPOSITIONS RELATED TO MODIFIED GUANINE BASES FOR CONTROLLING OFF-TARGET EFFECTS IN RNA INTERFERENCE
  申请人：Burrows Cynthia J.

  公开号：US20120095077A1

  公开（公告）日：2012-04-19

  Disclosed are compositions and methods related to modified nucleobases. Also disclosed are compositions and methods related to modified interfering RNAs. Also disclosed are compositions and methods related to modified guanine bases for controlling off-target effects in RNA interference.

  本发明涉及修饰核苷酸的组合物和方法。还涉及修饰干扰RNA的组合物和方法。还涉及修饰鸟嘌呤碱基以控制RNA干扰中的非特异性效应的组合物和方法。
• [EN] METHODS AND COMPOSITIONS RELATED TO MODIFIED GUANINE BASES FOR CONTROLLING OFF-TARGET EFFECTS IN RNA INTERFERENCE<br/>[FR] PROCÉDÉS ET COMPOSITIONS ASSOCIÉS À DES BASES GUANINE MODIFIÉES DESTINÉS À CONTRÔLER LES EFFETS DE FAUX-POSITIFS DANS L'INTERFÉRENCE PAR L'ARN
  申请人：UNIV UTAH RES FOUND

  公开号：WO2010111290A1

  公开（公告）日：2010-09-30

  Disclosed are compositions and methods related to modified nucleobases. Also disclosed are compositions and methods related to modified interfering RNAs. Also disclosed are compositions and methods related to modified guanine bases for controlling off-target effects in RNA interference.
• 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.