N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-8-chloropurin-6-yl]benzamide | 537697-48-6

• 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: N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-8-chloropurin-6-yl]benzamide
• CAS: 537697-48-6
• 化学式: C₃₈H₃₄ClN₅O₆
• 分子量: 692.171
• InChiKey: JSUPTIXKKQYBAA-DCMFLLSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  50
• 可旋转键数：
  11
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  双(二异丙基氨基)(2-氰基乙氧基)膦 、 N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-8-chloropurin-6-yl]benzamide 在 (iPr)2NH₂*CHN₄ 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以16%的产率得到N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyoxolan-2-yl]-8-chloropurin-6-yl]benzamide
  参考文献：
  名称：

  Effects of 8-chlorodeoxyadenosine on DNA synthesis by the klenow fragment of DNA polymerase I

  摘要：

  8-Chloro-2'-deoxyadenosine (8-Cl-dAdo) was incorporated into synthetic DNA oligonucleotides to determine its effects on DNA synthesis by the 3'-5' exonuclease-free Klenow fragment of Escherichia coli DNA Polymerase I (KF-). Single nucleotide insertion experiments were used to determine the coding potential of 8-Cl-dAdo in a DNA template. KF- inserted TTP opposite 8-Cl-dAdo in the template, but with decreased efficiency relative to natural deoxyadenosine. Running-start primer extensions with KF- resulted in polyrnerase pausing at 8-Cl-dAdo template sites during DNA synthesis. The 2'-deoxyribonucleoside triphosphate analogue, 8-Cl-dATP, was incorporated opposite thymidine (T) approximately two-fold less efficiently than dATP. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00204-x
• 作为产物：
  描述：

  2'-脱氧腺苷 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 ammonium hydroxide 、 四丁基氟化铵 、 对甲苯磺酰氯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.5h， 生成 N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-8-chloropurin-6-yl]benzamide
  参考文献：
  名称：

  Effects of 8-chlorodeoxyadenosine on DNA synthesis by the klenow fragment of DNA polymerase I

  摘要：

  8-Chloro-2'-deoxyadenosine (8-Cl-dAdo) was incorporated into synthetic DNA oligonucleotides to determine its effects on DNA synthesis by the 3'-5' exonuclease-free Klenow fragment of Escherichia coli DNA Polymerase I (KF-). Single nucleotide insertion experiments were used to determine the coding potential of 8-Cl-dAdo in a DNA template. KF- inserted TTP opposite 8-Cl-dAdo in the template, but with decreased efficiency relative to natural deoxyadenosine. Running-start primer extensions with KF- resulted in polyrnerase pausing at 8-Cl-dAdo template sites during DNA synthesis. The 2'-deoxyribonucleoside triphosphate analogue, 8-Cl-dATP, was incorporated opposite thymidine (T) approximately two-fold less efficiently than dATP. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00204-x

文献信息

• Effects of 8-chlorodeoxyadenosine on DNA synthesis by the klenow fragment of DNA polymerase I
  作者：Lisa S. Chen、Michael H. Bahr、Terry L. Sheppard

  DOI：10.1016/s0960-894x(03)00204-x

  日期：2003.5

  8-Chloro-2'-deoxyadenosine (8-Cl-dAdo) was incorporated into synthetic DNA oligonucleotides to determine its effects on DNA synthesis by the 3'-5' exonuclease-free Klenow fragment of Escherichia coli DNA Polymerase I (KF-). Single nucleotide insertion experiments were used to determine the coding potential of 8-Cl-dAdo in a DNA template. KF- inserted TTP opposite 8-Cl-dAdo in the template, but with decreased efficiency relative to natural deoxyadenosine. Running-start primer extensions with KF- resulted in polyrnerase pausing at 8-Cl-dAdo template sites during DNA synthesis. The 2'-deoxyribonucleoside triphosphate analogue, 8-Cl-dATP, was incorporated opposite thymidine (T) approximately two-fold less efficiently than dATP. (C) 2003 Elsevier Science Ltd. All rights reserved.