2-{5-[(2R,3R,4R,5R)-2-(6-Amino-purin-9-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yloxy]-pentyl}-isoindole-1,3-dione | 136834-17-8

• 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: 2-{5-[(2R,3R,4R,5R)-2-(6-Amino-purin-9-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yloxy]-pentyl}-isoindole-1,3-dione
• 英文别名: 2-[5-[(2R,3R,4R,5R)-2-(6-aminopurin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxypentyl]isoindole-1,3-dione
• CAS: 136834-17-8
• 化学式: C₂₃H₂₆N₆O₆
• 分子量: 482.496
• InChiKey: QFIJZBRYDPMKKY-CXIOKZBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.51
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  165.92
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2-{5-[(2R,3R,4R,5R)-2-(6-Amino-purin-9-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yloxy]-pentyl}-isoindole-1,3-dione 在 吡啶 、 ammonium hydroxide 、 三甲基氯硅烷 作用下， 生成 N-(9-{(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-[5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pentyloxy]-4-hydroxy-tetrahydro-furan-2-yl}-9H-purin-6-yl)-benzamide
  参考文献：
  名称：

  Novel functionalization of the sugar moiety of nucleic acids for multiple labeling in the minor groove

  摘要：

  The sugar ring of adenosine was alkylated at the 2'-O- position using N-(5-bromopentyl)phthalimide and the modified nucleoside was chemically incorporated into oligonucleotide diesters, thioates and RNA analogs. The free amino group, available after oligonucleotide deprotection, is useful for site-specific introduction of reporter groups and therapeutic agents at the 2'-position. This novel methodology permits multiple labeling of nucleic acids in the minor groove.

  DOI：

  10.1016/0040-4039(91)80468-l
• 作为产物：
  描述：

  N-(5-溴戊基)邻苯二甲酰亚胺 、 腺苷 在 sodium hydride 作用下， 生成 2-{5-[(2R,3R,4R,5R)-2-(6-Amino-purin-9-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yloxy]-pentyl}-isoindole-1,3-dione
  参考文献：
  名称：

  Novel functionalization of the sugar moiety of nucleic acids for multiple labeling in the minor groove

  摘要：

  The sugar ring of adenosine was alkylated at the 2'-O- position using N-(5-bromopentyl)phthalimide and the modified nucleoside was chemically incorporated into oligonucleotide diesters, thioates and RNA analogs. The free amino group, available after oligonucleotide deprotection, is useful for site-specific introduction of reporter groups and therapeutic agents at the 2'-position. This novel methodology permits multiple labeling of nucleic acids in the minor groove.

  DOI：

  10.1016/0040-4039(91)80468-l