β-D-3'-O-(N-methylanthraniloyl)-2'-deoxycytidine | 244183-90-2

• 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: β-D-3'-O-(N-methylanthraniloyl)-2'-deoxycytidine
• 英文别名: 3'-O-mant-2'-deoxycytidine；[(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-2-(hydroxymethyl)oxolan-3-yl] 2-(methylamino)benzoate
• CAS: 244183-90-2
• 化学式: C₁₇H₂₀N₄O₅
• 分子量: 360.37
• InChiKey: AOPYCYWTQLUEKQ-GZBFAFLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  127
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-甲基苯唑 、 2'-脱氧胞嘧啶核苷 生成 β-D-3'-O-(N-methylanthraniloyl)-2'-deoxycytidine
  参考文献：
  名称：

  Synthesis of New Fluorescent Nucleoside Analogues and Application to the Study of Human Deoxycytidine Kinase

  摘要：

  We have determined the affinity of human deoxycytidine kinase with respect to new fluorescent N-methylanthraniloyl cytidine derivatives or non fluorescent enantiomeric cytidine analogues. New results regarding the enantioselectivity and the mechanism of the enzyme are presented.

  DOI：

  10.1080/15257779908041552

文献信息

• Study of human deoxycytidine kinase binding properties using intrinsic fluorescence or new fluorescent ligands
  作者：Manijeh Shafiee、Gilles Gosselin、Jean-Louis Imbach、Gilles Divita、Staffan Eriksson、Georges Maury

  DOI：10.1016/s0223-5234(99)80092-0

  日期：1999.5

  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.
• Synthesis of New Fluorescent Nucleoside Analogues and Application to the Study of Human Deoxycytidine Kinase
  作者：M. Shafiee、G. Gosselin、J-L. Imbach、S. Eriksson、G. Maury

  DOI：10.1080/15257779908041552

  日期：1999.4

  We have determined the affinity of human deoxycytidine kinase with respect to new fluorescent N-methylanthraniloyl cytidine derivatives or non fluorescent enantiomeric cytidine analogues. New results regarding the enantioselectivity and the mechanism of the enzyme are presented.