5'-对甲苯磺酰基-2'-脱氧鸟苷 | 109954-64-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: 5'-对甲苯磺酰基-2'-脱氧鸟苷
• 中文别名: 5′-水合氯醛-2′-脱氧鸟苷
• 英文名称: 5'-tosyl-2'-deoxyguanosine
• 英文别名: 5'-O-tosyl-2'-dG；5'-O-tosyl-dG；5'-Tosyl-2'-deoxy Guanosine；[(2R,3S,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 109954-64-5
• 化学式: C₁₇H₁₉N₅O₆S
• 分子量: 421.434
• InChiKey: QZERCZKEESOISM-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  167
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5'-对甲苯磺酰基-2'-脱氧鸟苷 、 (Bu4N)3 OMDP 在 DOWEX AG-50W column (NH₄⁺) form 作用下， 以 乙腈 、 水 为溶剂， 以30%的产率得到
  参考文献：
  名称：

  α,β-Methylene-2′-deoxynucleoside 5′-Triphosphates as Noncleavable Substrates for DNA Polymerases: Isolation, Characterization, and Stability Studies of Novel 2′-Deoxycyclonucleosides, 3,5′-Cyclo-dG, and 2,5′-Cyclo-dT

  摘要：

  We report synthesis and characterization of a complete set of alpha,beta-methylene-2'-dNTPs (alpha,beta-m-dNTP; N = A, C, T, G, 12-15) in which the alpha,beta-oxygen linkage of natural dNTP was replaced by a methylene group. These nucleotides were designed to be noncleavable substrates for DNA polymerases. Synthesis entails preparation of 2'-deoxynucleoside 5'-diphosphate precursors, followed by an enzymatic gamma-phosphorylation. All four synthesized alpha,beta-m-dNTPs were found to be potent inhibitors of polymerase beta, with K-i values ranging 1-5 mu M. During preparation of the dG and dT derivatives of alpha,beta-methylene diphosphate, we also isolated significant amounts of 3,5'-cyclo-dG (16) and 2,5'-cyclo-dT (17), respectively. These novel 2'-deoxycyclonucleosides were formed via a base-catalyzed intramolecular cyclization (N3 -> C5' and O2 -> C5' respectively). In acidic solution, both 16 and 17 underwent glycolysis, followed by complete depurination. When exposed to alkaline conditions, 16 underwent an oxidative deamination to produce 3,5'-cyc1o-2'-deoxyxanthosine (19), whereas 17 was hydrolyzed exclusively to dT.

  DOI：

  10.1021/jm800692a
• 作为产物：
  描述：

  5'-O-tosyl-3'-O-(tert-butyldimethylsilyl)-2'-dG 在 氢氟酸 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 以70%的产率得到5'-对甲苯磺酰基-2'-脱氧鸟苷
  参考文献：
  名称：

  α,β-Methylene-2′-deoxynucleoside 5′-Triphosphates as Noncleavable Substrates for DNA Polymerases: Isolation, Characterization, and Stability Studies of Novel 2′-Deoxycyclonucleosides, 3,5′-Cyclo-dG, and 2,5′-Cyclo-dT

  摘要：

  We report synthesis and characterization of a complete set of alpha,beta-methylene-2'-dNTPs (alpha,beta-m-dNTP; N = A, C, T, G, 12-15) in which the alpha,beta-oxygen linkage of natural dNTP was replaced by a methylene group. These nucleotides were designed to be noncleavable substrates for DNA polymerases. Synthesis entails preparation of 2'-deoxynucleoside 5'-diphosphate precursors, followed by an enzymatic gamma-phosphorylation. All four synthesized alpha,beta-m-dNTPs were found to be potent inhibitors of polymerase beta, with K-i values ranging 1-5 mu M. During preparation of the dG and dT derivatives of alpha,beta-methylene diphosphate, we also isolated significant amounts of 3,5'-cyclo-dG (16) and 2,5'-cyclo-dT (17), respectively. These novel 2'-deoxycyclonucleosides were formed via a base-catalyzed intramolecular cyclization (N3 -> C5' and O2 -> C5' respectively). In acidic solution, both 16 and 17 underwent glycolysis, followed by complete depurination. When exposed to alkaline conditions, 16 underwent an oxidative deamination to produce 3,5'-cyc1o-2'-deoxyxanthosine (19), whereas 17 was hydrolyzed exclusively to dT.

  DOI：

  10.1021/jm800692a

文献信息

• Method for the synthesis of isoguanosine and its 2'-derivatives
  申请人：Bayer Corporation

  公开号：EP1097939A2

  公开（公告）日：2001-05-09

  Methods are provided for substantially reducing background signals encountered in nucleic acid hybridization assays. The method is premised on the elimination or significant reduction of the phenomenon of nonspecific hybridization, so as to provide a detectable signal which is produced only in the presence of the target polynucleotide of interest. In addition, a novel method for the chemical synthesis of isoguanosine or 2'-deoxy-isoguanosine is provided. The invention also has applications in antisense and aptamer therapeutics and drug discovery.

  本发明提供了大幅降低核酸杂交试验中背景信号的方法。该方法的前提是消除或显著减少非特异性杂交现象，从而提供仅在目标多核苷酸存在时才会产生的可检测信号。此外，本发明还提供了一种化学合成异鸟苷或 2'- 脱氧异鸟苷的新方法。本发明还可应用于反义和适配体疗法以及药物发现。
• Reduction of nonspecific hybridization by using novel base-pairing schemes
  申请人：——

  公开号：US20010026918A1

  公开（公告）日：2001-10-04

  Methods are provided for substantially reducing background signals encountered in nucleic acid hybridization assays. The method is premised on the elimination or significant reduction of the phenomenon of nonspecific hybridization, so as to provide a detectable signal which is produced only in the presence the target polynucleotide of interest. In addition, a novel method for the chemical synthesis of isoguanosine or 2′-deoxy-isoguanosine is provided. The invention also has applications in antisense and aptamer therapeutics and drug discovery.

  本发明提供了大幅降低核酸杂交试验中背景信号的方法。该方法的前提是消除或显著减少非特异性杂交现象，从而提供仅在目标多核苷酸存在时才产生的可检测信号。此外，本发明还提供了一种化学合成异鸟苷或 2′-脱氧异鸟苷的新方法。本发明还可应用于反义和适配体治疗以及药物发现。
• REDUCTION OF NONSPECIFIC HYBRIDIZATION BY USING NOVEL BASE-PAIRING SCHEMES
  申请人：CHIRON CORPORATION

  公开号：EP0778898A1

  公开（公告）日：1997-06-18
• Method for the synthesis of isoguanosine and of its 2'-derivatives
  申请人：Bayer Corporation

  公开号：EP1097939B1

  公开（公告）日：2004-02-11
• US6232462B1
  申请人：——

  公开号：US6232462B1

  公开（公告）日：2001-05-15