α-2-nitrobenzyl 1'-cyano-5'-O-(4-monomethoxytrityl)-2'-deoxy-D-ribofuranoside | 357282-05-4

• 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: α-2-nitrobenzyl 1'-cyano-5'-O-(4-monomethoxytrityl)-2'-deoxy-D-ribofuranoside
• CAS: 357282-05-4
• 化学式: C₃₃H₃₀N₂O₇
• 分子量: 566.61
• InChiKey: DCLKQMAEEGSVHT-DCMFLLSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  124.08
• 氢给体数：
  1.0
• 氢受体数：
  8.0

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 、 α-2-nitrobenzyl 1'-cyano-5'-O-(4-monomethoxytrityl)-2'-deoxy-D-ribofuranoside 在 (i-Pr)2NH₂*CHN₄ 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到α-2-nitrobenzyl 1'-cyano-3'-O-(2-cyanoethyl N,N-diisopropylphosphoramidyl)-5'O-(4-monomethoxytrityl)-2'-deoxy-D-ribofuranoside
  参考文献：
  名称：

  Site-Specific Generation of Deoxyribonolactone Lesions in DNA Oligonucleotides

  摘要：

  [GRAPHICS]An efficient method for the site specific generation of 2-deoxyribonolactone oxidative DNA damage lesions from a "photocaged" nucleoside analogue was developed. A nucleoside phosphoramidite bearing a C-1 ' nitrobenzyl cyanohydrin was prepared and incorporated into DNA oligonucleotides using automated DNA synthesis. The caged analogue, which was stable in aqueous solution, was converted to the 2-deoxyribonolactone lesion by UV irradiation. DNA containing the caged analogue and the deoxyribonolactone site were characterized by electrospray mass spectrometry (ES-MS).

  DOI：

  10.1021/ol016255e
• 作为产物：
  描述：

  1-氯-3,5-二对氯苯甲酰氧基-2-脱氧-D-核糖 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 氨 、 silver trifluoromethanesulfonate 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 吡啶 、 四氯化碳 、 二氯甲烷 为溶剂， 反应 31.5h， 生成 α-2-nitrobenzyl 1'-cyano-5'-O-(4-monomethoxytrityl)-2'-deoxy-D-ribofuranoside
  参考文献：
  名称：

  Site-Specific Generation of Deoxyribonolactone Lesions in DNA Oligonucleotides

  摘要：

  [GRAPHICS]An efficient method for the site specific generation of 2-deoxyribonolactone oxidative DNA damage lesions from a "photocaged" nucleoside analogue was developed. A nucleoside phosphoramidite bearing a C-1 ' nitrobenzyl cyanohydrin was prepared and incorporated into DNA oligonucleotides using automated DNA synthesis. The caged analogue, which was stable in aqueous solution, was converted to the 2-deoxyribonolactone lesion by UV irradiation. DNA containing the caged analogue and the deoxyribonolactone site were characterized by electrospray mass spectrometry (ES-MS).

  DOI：

  10.1021/ol016255e