2'-O-[2-[[N-methyl-N-(2-phthalimidoethyl)amino]oxy]ethyl]-5-methyluridine | 258501-35-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 2'-O-[2-[[N-methyl-N-(2-phthalimidoethyl)amino]oxy]ethyl]-5-methyluridine
• 英文别名: 2-[2-[2-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-2-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyethoxy-methylamino]ethyl]isoindole-1,3-dione
• CAS: 258501-35-8
• 化学式: C₂₃H₂₈N₄O₉
• 分子量: 504.497
• InChiKey: NRFUIYNNFIMHSW-OZQHCQBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  158
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2'-O-[2-[[N-methyl-N-(2-phthalimidoethyl)amino]oxy]ethyl]-5-methyluridine 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 5'-O-(4,4'-dimethoxytrityl)-2'-O-[2-[[N-methyl-N-(2-phthalimidoethyl)amino]oxy]ethyl]-3'-O-succinyl-5-methyluridine
  参考文献：
  名称：

  Synthesis of 2′-O-[2-[(N,N-dialkylamino)oxy]ethyl]-modified oligonucleotides: hybridization affinity, resistance to nuclease, and protein binding characteristics

  摘要：

  Synthesis of a series of 2'-O- [2-[(N,N-dialkylamino)oxy]ethyl]-modified 5-methyluridine nucleoside phosphoramidites and solid supports are described. Using these monomers, modified oligonucleotides containing phosphodiester linkages were synthesized in high yields. These modified oligonucleotides showed enhanced binding affinity to the complementary RNA (and not to DNA) and excellent nuclease stability with t(1/2)>24 It. The human serum albumin binding properties of modified oligonucleotides have been evaluated to assess their transport and toxicity properties. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/s0040-4020(03)01104-9
• 作为产物：
  描述：

  苯二甲酰亚氨基乙醛 在 triethylamine trihydrofluoride 、 4-甲基苯磺酸吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 22.42h， 生成 2'-O-[2-[[N-methyl-N-(2-phthalimidoethyl)amino]oxy]ethyl]-5-methyluridine
  参考文献：
  名称：

  Synthesis of 2′-O-[2-[(N,N-dialkylamino)oxy]ethyl]-modified oligonucleotides: hybridization affinity, resistance to nuclease, and protein binding characteristics

  摘要：

  Synthesis of a series of 2'-O- [2-[(N,N-dialkylamino)oxy]ethyl]-modified 5-methyluridine nucleoside phosphoramidites and solid supports are described. Using these monomers, modified oligonucleotides containing phosphodiester linkages were synthesized in high yields. These modified oligonucleotides showed enhanced binding affinity to the complementary RNA (and not to DNA) and excellent nuclease stability with t(1/2)>24 It. The human serum albumin binding properties of modified oligonucleotides have been evaluated to assess their transport and toxicity properties. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/s0040-4020(03)01104-9

文献信息

• Synthesis of 2′-O-[2-[(N,N-dialkylamino)oxy]ethyl]-modified oligonucleotides: hybridization affinity, resistance to nuclease, and protein binding characteristics
  作者：Thazha P Prakash、Andrew M Kawasaki、Elena A Lesnik、Namir Sioufi、Muthiah Manoharan

  DOI：10.1016/s0040-4020(03)01104-9

  日期：2003.9

  Synthesis of a series of 2'-O- [2-[(N,N-dialkylamino)oxy]ethyl]-modified 5-methyluridine nucleoside phosphoramidites and solid supports are described. Using these monomers, modified oligonucleotides containing phosphodiester linkages were synthesized in high yields. These modified oligonucleotides showed enhanced binding affinity to the complementary RNA (and not to DNA) and excellent nuclease stability with t(1/2)>24 It. The human serum albumin binding properties of modified oligonucleotides have been evaluated to assess their transport and toxicity properties. (C) 2003 Published by Elsevier Ltd.