N4-benzoyl-2'-deoxycytidine-5'-tosylate | 5174-26-5

• 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: N4-benzoyl-2'-deoxycytidine-5'-tosylate
• 英文别名: N⁴-benzoyl-O^5'-(toluene-4-sulfonyl)-2'deoxy-cytidine；N-Benzoyl-2'-deoxy-cytidin-5'-p-toluolsulfonat；[(2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 5174-26-5
• 化学式: C₂₃H₂₃N₃O₇S
• 分子量: 485.518
• InChiKey: XQKJIEIKFAPXQD-QKNQBKEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  143
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N4-benzoyl-2'-deoxycytidine-5'-tosylate 在 palladium on activated charcoal 吡啶 、 叠氮化锂 、 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 N⁴-benzoyl-2',5'-dideoxy-5'-(4''-monomethoxytrityl)aminocytidine
  参考文献：
  名称：

  DNG cytidine: synthesis and binding properties of octameric guanidinium-linked deoxycytidine oligomer

  摘要：

  The synthesis of guanidinium-linked cytidyl oligomer (DNG-C-8), a cationic DNA analog, and the corresponding cytidine monomers is described. The DNG monomer synthesis was streamlined to produce a shorter route to the final monomer than previously reported for thymidine and subsequent solid-phase synthesis produced an octameric cytidyl DNG strand. Because octameric deoxyguanosine would be used as the complementary strand in our studies, it was necessary to investigate guanosine self-association. Singular value decomposition was used to mathematically deconvolve the spectral data and confirm the presence of transitions due to DNA-G(8) self-association. Job plots show the binding stoichiometry of DNG-C-8 with DNA-G(8) to be 1: 1. Thermal denaturation studies of the DNG-C-8-DNA-G(8) duplex established a T-m greater than or equal to 90degreesC and a DeltaGdegrees = 13.3 kcal mol(-1), indicating the DNG-C(8)(.)DNA-G(8) duplex is over 1000 times more stable than that of DNA-C(8)(.)DNA-G(8). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.010
• 作为产物：
  描述：

  2'-脱氧胞嘧啶核苷 在 吡啶 、 三甲基氯硅烷 作用下， 反应 3.0h， 生成 N4-benzoyl-2'-deoxycytidine-5'-tosylate
  参考文献：
  名称：

  Pyrimidine-Purine and Pyrimidine Heterodinucleosides Synthesis Containing a Triazole Linkage

  摘要：

  This article describes a synthetic route to generate two purine-pyrimidine and pyrimidine heterodinucleosides. Both microwave activated regioselective alkylation using hydride and copper-catalyzed-azide-alkyne-cycloaddition (CuAAC) were used in order to perform the synthesis.

  DOI：

  10.1080/15257771003708579

文献信息

• α,β-Difluoromethylene Deoxynucleoside 5′-Triphosphates: A Convenient Synthesis of Useful Probes for DNA Polymerase β Structure and Function
  作者：Thomas G. Upton、Boris A. Kashemirov、Charles E. McKenna、Myron F. Goodman、G. K. Surya Prakash、Roman Kultyshev、Vinod K. Batra、David D. Shock、Lars C. Pedersen、William A. Beard、Samuel H. Wilson

  DOI：10.1021/ol701755k

  日期：2009.5.7

  β-Difluoromethylene deoxynucleoside 5′-triphosphates (dNTPs, N = A or C) are advantageously obtained via phosphorylation of corresponding dNDP analogues using catalytic ATP, PEP, nucleoside diphosphate kinase, and pyruvate kinase. DNA pol β Kd values for the α,β-CF2 and unmodified dNTPs, α,β-NH dUTP, and the α,β-CH2 analogues of dATP and dGTP are discussed in relation to the conformations of α,β-CF2 dTTP versus

  α,β-二氟亚甲基脱氧核苷 5'-三磷酸（dNTP，N = A 或 C）有利地通过使用催化 ATP、PEP、核苷二磷酸激酶和丙酮酸激酶对相应的 dNDP 类似物进行磷酸化获得。α,β-CF 2和未修饰的 dNTP、α,β-NH dUTP 以及dATP 和 dGTP的 α,β-CH 2类似物的DNA pol β K d值与 α,β-的构象有关CF 2 dTTP 与结合到酶活性位点的 α,β-NH dUTP。
• Pyrimidine-Purine and Pyrimidine Heterodinucleosides Synthesis Containing a Triazole Linkage
  作者：R. Lucas、P. H. Elchinger、P. A. Faugeras、R. Zerrouki

  DOI：10.1080/15257771003708579

  日期：2010.4.20

  This article describes a synthetic route to generate two purine-pyrimidine and pyrimidine heterodinucleosides. Both microwave activated regioselective alkylation using hydride and copper-catalyzed-azide-alkyne-cycloaddition (CuAAC) were used in order to perform the synthesis.
• DNG cytidine: synthesis and binding properties of octameric guanidinium-linked deoxycytidine oligomer
  作者：Istvan E. Szabo、Thomas C. Bruice

  DOI：10.1016/j.bmc.2004.05.010

  日期：2004.8.1

  The synthesis of guanidinium-linked cytidyl oligomer (DNG-C-8), a cationic DNA analog, and the corresponding cytidine monomers is described. The DNG monomer synthesis was streamlined to produce a shorter route to the final monomer than previously reported for thymidine and subsequent solid-phase synthesis produced an octameric cytidyl DNG strand. Because octameric deoxyguanosine would be used as the complementary strand in our studies, it was necessary to investigate guanosine self-association. Singular value decomposition was used to mathematically deconvolve the spectral data and confirm the presence of transitions due to DNA-G(8) self-association. Job plots show the binding stoichiometry of DNG-C-8 with DNA-G(8) to be 1: 1. Thermal denaturation studies of the DNG-C-8-DNA-G(8) duplex established a T-m greater than or equal to 90degreesC and a DeltaGdegrees = 13.3 kcal mol(-1), indicating the DNG-C(8)(.)DNA-G(8) duplex is over 1000 times more stable than that of DNA-C(8)(.)DNA-G(8). (C) 2004 Elsevier Ltd. All rights reserved.