β-D-5'-O,N⁴-bis(4-methoxytrityl)cytidine | 250581-85-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: β-D-5'-O,N⁴-bis(4-methoxytrityl)cytidine
• 英文别名: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]oxolan-2-yl]-4-[[(4-methoxyphenyl)-diphenylmethyl]amino]pyrimidin-2-one
• CAS: 250581-85-2
• 化学式: C₄₉H₄₅N₃O₇
• 分子量: 787.912
• InChiKey: HLMOIDJVMVHPKK-KYJNYJMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  59
• 可旋转键数：
  14
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-甲基苯唑 、 β-D-5'-O,N⁴-bis(4-methoxytrityl)cytidine 在 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 76.0h， 生成 β-D-3'-O-(N-methylanthraniloyl)cytidine 、 β-D-2'-O-(N-methylanthraniloyl)cytidine
  参考文献：
  名称：

  Study of human deoxycytidine kinase binding properties using intrinsic fluorescence or new fluorescent ligands

  摘要：

  A series of D- and L-enantiomers of cytidine or adenosine analogues and fluorescent N-methylanthraniloyl (MeNHBz) cytidine derivatives regiospecifically synthesized from cytidine or deoxycytidine were used to quantify the enantioselectivity of human deoxycytidine kinase (dCK) and to characterize its binding states. Both D- and L-enantiomers of these compounds induced significant bimodal quenchings of the intrinsic fluorescence of the enzyme. The ratios of dissociation constants Kd(D)/Kd(L) for the high affinity binding of non fluorescent cytidine derivatives were remarkably similar. beta-D- and beta-L-ATP gave monophasic titration curves and the enzyme displayed a preference for the natural enantiomer. This demonstrates the lack of enantioselectivity of dCK in the substrate binding steps of its mechanism. The results of other fluorescence experiments with MeNHBz-cytidine derivatives were consistent with an enzyme mechanism in which nucleotide binding precedes nucleoside binding. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80092-0
• 作为产物：
  描述：

  4-甲氧基三苯基氯甲烷 、 胞苷 反应 12.0h， 以74%的产率得到β-D-5'-O,N⁴-bis(4-methoxytrityl)cytidine
  参考文献：
  名称：

  Study of human deoxycytidine kinase binding properties using intrinsic fluorescence or new fluorescent ligands

  摘要：

  A series of D- and L-enantiomers of cytidine or adenosine analogues and fluorescent N-methylanthraniloyl (MeNHBz) cytidine derivatives regiospecifically synthesized from cytidine or deoxycytidine were used to quantify the enantioselectivity of human deoxycytidine kinase (dCK) and to characterize its binding states. Both D- and L-enantiomers of these compounds induced significant bimodal quenchings of the intrinsic fluorescence of the enzyme. The ratios of dissociation constants Kd(D)/Kd(L) for the high affinity binding of non fluorescent cytidine derivatives were remarkably similar. beta-D- and beta-L-ATP gave monophasic titration curves and the enzyme displayed a preference for the natural enantiomer. This demonstrates the lack of enantioselectivity of dCK in the substrate binding steps of its mechanism. The results of other fluorescence experiments with MeNHBz-cytidine derivatives were consistent with an enzyme mechanism in which nucleotide binding precedes nucleoside binding. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80092-0