3'-O-(azidomethyl)-5'-O-benzoylthymidine | 139433-18-4

• 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: 3'-O-(azidomethyl)-5'-O-benzoylthymidine
• 英文别名: [(2R,3S,5R)-3-(azidomethoxy)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 139433-18-4
• 化学式: C₁₈H₁₉N₅O₆
• 分子量: 401.379
• InChiKey: UQYRHMGMLITBDL-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3'-O-(azidomethyl)-5'-O-benzoylthymidine 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以94.6%的产率得到3'-O-(azidomethyl)-2'-deoxythymidine
  参考文献：
  名称：

  Synthesis of Triazole-Linked Oligonucleotides with High Affinity to DNA Complements and an Analysis of Their Compatibility with Biosystems

  摘要：

  New oligonucleotide analogues with triazole internucleotide linkages were synthesized, and their hybridization properties were studied. The analogues demonstrated DNA binding affinities similar to those of unmodified oligonucleotides. The modification was shown to protect the oligonucleotides from nuclease hydrolysis. The modified oligonucleotides were tested as PCR primers. Modifications remote from the 3'-terminus were tolerated by polymerases. Our results suggest that these new oligonucleotide analogues are among the most promising triazole DNA mimics characterized to date.

  DOI：

  10.1021/jo400651k
• 作为产物：
  描述：

  5'-benzoylthymidine 在 溴 、 乙酸酐 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 反应 74.67h， 生成 3'-O-(azidomethyl)-5'-O-benzoylthymidine
  参考文献：
  名称：

  Synthesis of Triazole-Linked Oligonucleotides with High Affinity to DNA Complements and an Analysis of Their Compatibility with Biosystems

  摘要：

  New oligonucleotide analogues with triazole internucleotide linkages were synthesized, and their hybridization properties were studied. The analogues demonstrated DNA binding affinities similar to those of unmodified oligonucleotides. The modification was shown to protect the oligonucleotides from nuclease hydrolysis. The modified oligonucleotides were tested as PCR primers. Modifications remote from the 3'-terminus were tolerated by polymerases. Our results suggest that these new oligonucleotide analogues are among the most promising triazole DNA mimics characterized to date.

  DOI：

  10.1021/jo400651k

文献信息

• Synthesis of Triazole-Linked Oligonucleotides with High Affinity to DNA Complements and an Analysis of Their Compatibility with Biosystems
  作者：Anna M. Varizhuk、Dmitry N. Kaluzhny、Roman A. Novikov、Alexandr O. Chizhov、Igor P. Smirnov、Andrey N. Chuvilin、Olga N. Tatarinova、Gleb Y. Fisunov、Galina E. Pozmogova、Vladimir L. Florentiev

  DOI：10.1021/jo400651k

  日期：2013.6.21

  New oligonucleotide analogues with triazole internucleotide linkages were synthesized, and their hybridization properties were studied. The analogues demonstrated DNA binding affinities similar to those of unmodified oligonucleotides. The modification was shown to protect the oligonucleotides from nuclease hydrolysis. The modified oligonucleotides were tested as PCR primers. Modifications remote from the 3'-terminus were tolerated by polymerases. Our results suggest that these new oligonucleotide analogues are among the most promising triazole DNA mimics characterized to date.