β-D-5'-O-(N-methylanthraniloyl)-N⁴,3'-O-bis(4-methoxytrityl)-2'-deoxycytidine | 250581-90-9

• 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-(N-methylanthraniloyl)-N⁴,3'-O-bis(4-methoxytrityl)-2'-deoxycytidine
• 英文别名: [(2R,3S,5R)-3-[(4-methoxyphenyl)-diphenylmethoxy]-5-[4-[[(4-methoxyphenyl)-diphenylmethyl]amino]-2-oxopyrimidin-1-yl]oxolan-2-yl]methyl 2-(methylamino)benzoate
• CAS: 250581-90-9
• 化学式: C₅₇H₅₂N₄O₇
• 分子量: 905.062
• InChiKey: ROVXPYSIBCYKAA-CCCGGDKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  68
• 可旋转键数：
  18
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  β-D-5'-O-(N-methylanthraniloyl)-N⁴,3'-O-bis(4-methoxytrityl)-2'-deoxycytidine 在 溶剂黄146 作用下， 反应 48.0h， 以75%的产率得到β-D-5'-O-(N-methylanthraniloyl)-2'-deoxycytidine
  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：

  5'-O-(tert-butyldimethylsilyl)-2'-deoxycytidine 在 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 β-D-5'-O-(N-methylanthraniloyl)-N⁴,3'-O-bis(4-methoxytrityl)-2'-deoxycytidine
  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