2'-deoxy-1'β-(2-nitropiperonyl)-3',5'-di-O-toluoyl-D-ribofuranose | 255394-89-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-deoxy-1'β-(2-nitropiperonyl)-3',5'-di-O-toluoyl-D-ribofuranose
• 英文别名: [(2R,3S,5R)-3-(4-methylbenzoyl)oxy-5-(6-nitro-1,3-benzodioxol-5-yl)oxolan-2-yl]methyl 4-methylbenzoate
• CAS: 255394-89-9
• 化学式: C₂₈H₂₅NO₉
• 分子量: 519.508
• InChiKey: ZEQAWIAIWTURRP-ZSQFBXSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2'-deoxy-1'β-(2-nitropiperonyl)-3',5'-di-O-toluoyl-D-ribofuranose 在 4-二甲氨基吡啶 、 sodium methylate 、 三乙胺 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 6.75h， 生成 2'-deoxy-1'β-(2-nitropiperonyl)-5'-O-dimethoxytrityl-D-ribofuranose
  参考文献：
  名称：

  A Universal, Photocleavable DNA Base:  Nitropiperonyl 2‘-Deoxyriboside

  摘要：

  A universal, photochemically cleavable DNA base analogue would add desirable versatility to a number of methods in molecular biology. A novel C-nucleoside, nitropiperonyl deoxyriboside (NPdR, P*), has been investigated for this purpose. NPdR can be converted to its 5 ' -DMTr-3 ' -CEphosphoramidite and was incorporated into pentacosanucleotides by conventional synthesis techniques. The destabilizing effect on hybrid formation with a complementary strand when this P* base opposes A, T, and G was found to be 3-5 kcal/mol, but 9 kcal/mol when it opposes C. Brief irradiation (lambda > 360 nm, 20 min) of DNA containing the P* base and piperidine treatment causes strand cleavage giving the 3 '- and 5 ' -phosphates. Two significant recent interests, universal/non-hydrogen-bonding base analogues and photochemical backbone cleavage, have thus been combined in a single molecule that serves as a light-based DNA scissors.

  DOI：

  10.1021/jo001594r
• 作为产物：
  描述：

  1-Α-氯-3,5-二-O-对甲苯甲酰基-2-脱氧-D-呋喃核糖 在 硫酸 、 碘 、 copper(II) nitrate 、 对甲苯磺酸 、 magnesium 、 cadmium(II) chloride 作用下， 以 四氢呋喃 、 水 、 乙酸酐 、 甲苯 为溶剂， 反应 12.92h， 生成 2'-deoxy-1'β-(2-nitropiperonyl)-3',5'-di-O-toluoyl-D-ribofuranose
  参考文献：
  名称：

  A Universal, Photocleavable DNA Base:  Nitropiperonyl 2‘-Deoxyriboside

  摘要：

  A universal, photochemically cleavable DNA base analogue would add desirable versatility to a number of methods in molecular biology. A novel C-nucleoside, nitropiperonyl deoxyriboside (NPdR, P*), has been investigated for this purpose. NPdR can be converted to its 5 ' -DMTr-3 ' -CEphosphoramidite and was incorporated into pentacosanucleotides by conventional synthesis techniques. The destabilizing effect on hybrid formation with a complementary strand when this P* base opposes A, T, and G was found to be 3-5 kcal/mol, but 9 kcal/mol when it opposes C. Brief irradiation (lambda > 360 nm, 20 min) of DNA containing the P* base and piperidine treatment causes strand cleavage giving the 3 '- and 5 ' -phosphates. Two significant recent interests, universal/non-hydrogen-bonding base analogues and photochemical backbone cleavage, have thus been combined in a single molecule that serves as a light-based DNA scissors.

  DOI：

  10.1021/jo001594r

文献信息

• A Universal, Photocleavable DNA Base:  Nitropiperonyl 2‘-Deoxyriboside
  作者：Michael C. Pirrung、Xiaodong Zhao、Shannon V. Harris

  DOI：10.1021/jo001594r

  日期：2001.3.1

  A universal, photochemically cleavable DNA base analogue would add desirable versatility to a number of methods in molecular biology. A novel C-nucleoside, nitropiperonyl deoxyriboside (NPdR, P*), has been investigated for this purpose. NPdR can be converted to its 5 ' -DMTr-3 ' -CEphosphoramidite and was incorporated into pentacosanucleotides by conventional synthesis techniques. The destabilizing effect on hybrid formation with a complementary strand when this P* base opposes A, T, and G was found to be 3-5 kcal/mol, but 9 kcal/mol when it opposes C. Brief irradiation (lambda > 360 nm, 20 min) of DNA containing the P* base and piperidine treatment causes strand cleavage giving the 3 '- and 5 ' -phosphates. Two significant recent interests, universal/non-hydrogen-bonding base analogues and photochemical backbone cleavage, have thus been combined in a single molecule that serves as a light-based DNA scissors.