2-nitrobenzyl 3-O-(2-cyanoethyl)-N,N-diisopropylphosphoramidyl-4-methoxy-5-O-(4,4'-dimethoxytrityl)-2-deoxy-D-ribofuranoside | 1005174-08-2

• 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: 2-nitrobenzyl 3-O-(2-cyanoethyl)-N,N-diisopropylphosphoramidyl-4-methoxy-5-O-(4,4'-dimethoxytrityl)-2-deoxy-D-ribofuranoside
• 英文别名: 3-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-2-methoxy-5-[(2-nitrophenyl)methoxy]oxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
• CAS: 1005174-08-2
• 化学式: C₄₃H₅₂N₃O₁₀P
• 分子量: 801.874
• InChiKey: QHLSKJJHRAMWPW-RHAUBNDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  57
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  147
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  2-nitrobenzyl 4-methoxy-5-O-(4,4'-dimethoxytrityl)-2-deoxy-D-ribofuranoside 、 双(二异丙基氨基)(2-氰基乙氧基)膦 在 四氮唑 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 以79%的产率得到2-nitrobenzyl 3-O-(2-cyanoethyl)-N,N-diisopropylphosphoramidyl-4-methoxy-5-O-(4,4'-dimethoxytrityl)-2-deoxy-D-ribofuranoside
  参考文献：
  名称：

  Photochemical Generation of Oligodeoxynucleotide Containing a C4‘-Oxidized Abasic Site and Its Efficient Amine Modification:  Dependence on Structure and Microenvironment

  摘要：

  [GRAPHICS]Bleomycin-induced oxidative DNA damage under limited oxygen conditions results in the formation of the C4'-oxidized abasic site (1). We synthesized the oligodeoxynucleotides (ODN) 5, which contains 4'-o-nitrobenzyloxythymidine (3), and 6, which contains 2-nitrobenzyloxy-4'-methoxy-2'-deoxy-D-ribofuranoside (4), as the caged precursors of 7, an ODN containing 1, to study its reactivity with amines. Photoirradiation of the single- and double-stranded 5 led to the formation of 7. Uncaging of the duplex was faster and the yield of 7 was higher with the double-stranded than with the single-stranded ODN. It was suggested that a low dielectric environment of the o-nitrobenzyloxy group in the minor groove of the duplex might accelerate the uncaging rate. Similarly, 6 and its duplex yielded 7 by photoirradiation. However, the yields of 7 were lower than those of 5, and duplex formation slowed the uncaging rate. Reaction of the obtained 7 with an amine resulted in the formation of the lactam 2b in good yield in both single- and double-stranded forms, showing that amine modification of biomolecules by an ODN containing 1 is possible under physiologic conditions.

  DOI：

  10.1021/jo702080r

文献信息

• Photochemical Generation of Oligodeoxynucleotide Containing a C4‘-Oxidized Abasic Site and Its Efficient Amine Modification:  Dependence on Structure and Microenvironment
  作者：Kazuteru Usui、Mariko Aso、Mitsuhiro Fukuda、Hiroshi Suemune

  DOI：10.1021/jo702080r

  日期：2008.1.1

  [GRAPHICS]Bleomycin-induced oxidative DNA damage under limited oxygen conditions results in the formation of the C4'-oxidized abasic site (1). We synthesized the oligodeoxynucleotides (ODN) 5, which contains 4'-o-nitrobenzyloxythymidine (3), and 6, which contains 2-nitrobenzyloxy-4'-methoxy-2'-deoxy-D-ribofuranoside (4), as the caged precursors of 7, an ODN containing 1, to study its reactivity with amines. Photoirradiation of the single- and double-stranded 5 led to the formation of 7. Uncaging of the duplex was faster and the yield of 7 was higher with the double-stranded than with the single-stranded ODN. It was suggested that a low dielectric environment of the o-nitrobenzyloxy group in the minor groove of the duplex might accelerate the uncaging rate. Similarly, 6 and its duplex yielded 7 by photoirradiation. However, the yields of 7 were lower than those of 5, and duplex formation slowed the uncaging rate. Reaction of the obtained 7 with an amine resulted in the formation of the lactam 2b in good yield in both single- and double-stranded forms, showing that amine modification of biomolecules by an ODN containing 1 is possible under physiologic conditions.