2',3'-O-异亚丙基胞苷盐酸盐 | 57977-73-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 2',3'-O-异亚丙基胞苷盐酸盐
• 英文名称: β-D-2',3'-O-(isopropylidene)cytidine hydrochloride
• 英文别名: 2',3'-O-isopropylidenecytidine hydrochloride；1-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-4-aminopyrimidin-2-one;hydrochloride
• CAS: 57977-73-8
• 化学式: C₁₂H₁₇N₃O₅*ClH
• 分子量: 319.745
• InChiKey: QHLLFDHNDAUUFG-RQDZQORCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2',3'-O-异亚丙基胞苷盐酸盐 在 甲酸 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 88.0h， 生成 β-D-5'-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

文献信息

• O-selective phosphorylation of nucleosides without N-protection
  作者：Mamoru Uchiyama、Yoshio Aso、Ryoji Noyori、Yoshihiro Hayakawa

  DOI：10.1021/jo00054a020

  日期：1993.1

  A facile chemoselective O-phosphorylation of N-unprotected nucleosides has been achieved via metal alkoxide formation. Sequential treatment of N-unprotected nucleosides with an equimolar amount of a metallo-organic base such as an alkyllithium, potassium tert-butoxide, tert-butylmagnesium chloride, LiAl[N(CH3)2]4, Al[N(CH3)2]3, (i-C4H9)2AlH, etc., and a phosphorochloridate or p-nitrophenyl phosphate results in rapid O-phosphorylation to give the corresponding nucleotides in high yield. The method using magnesium alkoxides is among the best, considering its chemoselectivity, generality, and operational simplicity. The origin of the observed chemoselectivity is discussed.