9-β-D-Arabinofuranosylguanine 5'-Monophosphate | 59981-79-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: 9-β-D-Arabinofuranosylguanine 5'-Monophosphate
• 英文别名: Guanine arabinose-5'-phosphate；[(2R,3S,4S,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
• CAS: 59981-79-2
• 化学式: C₁₀H₁₄N₅O₈P
• 分子量: 363.224
• InChiKey: RQFCJASXJCIDSX-FJFJXFQQSA-N

物化性质

• 密度：
  2.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  202
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  9-Β-D-糖呋喃鸟嘌呤 在 三氯氧磷 作用下， 以 various solvent(s) 为溶剂， 以48%的产率得到9-β-D-Arabinofuranosylguanine 5'-Monophosphate
  参考文献：
  名称：

  2'-脱氧-6-硫代鸟苷，的一种方便的合成ARA -鸟嘌呤，阿糖胞苷-6-硫鸟嘌呤和某些相关嘌呤核苷通过立体有择钠盐的糖基化过程†

  摘要：

  使用立体特异性钠盐糖基化方法已经完成了生物学上重要的2'-脱氧-6-硫鸟嘌呤（11），ara -6-硫鸟嘌呤（16）和ara G（17）的简单且高收率的合成。6-氯-和2-氨基-6-氯嘌呤（分别为1和2）的钠盐与1-氯-2-脱氧-3,5-二-O-（对甲苯甲酰基）-α-的糖基化D-赤型-五呋喃糖（3）给出了相应的N-9取代核苷，它们是具有β-端基异构体构型的主要产物（4和5，以及少量的N-7位置异构体（6和7）。在含有甲醇钠的甲醇中用硫化氢处理4，以93％的收率得到2'-deoxy-6-thioinosine（10）。类似地，将5以71％的产率转化为2'-脱氧-6-硫鸟苷（β-TGdR，11）。2的钠盐与1-氯-2,3,5-三-O-苄基-α-D-阿拉伯呋喃糖（8）的反应分别得到N-7和N-9糖基化产物13和9。9的脱苄基作用用三氯化硼在-78°下用62％的收率得到通用的中间体2-氨基-6-氯

  DOI：

  10.1002/jhet.5570250653

文献信息

• A convenient synthesis of 2′-deoxy-6-thioguanosine,<i>ara</i>-guanine,<i>ara</i>-6-thioguanine and certain related purine nucleosides by the stereospecific sodium salt glycosylation procedure
  作者：Naeem B. Hanna、Kandasamy Ramasamy、Roland K. Robins、Ganapathi R. Revankar

  DOI：10.1002/jhet.5570250653

  日期：1988.11

  A simple and high-yield synthesis of biologically significant 2′-deoxy-6-thioguanosine (11), ara-6-thioguanine (16) and araG (17) has been accomplished employing the Stereospecific sodium salt glycosylation method. Glycosylation of the sodium salt of 6-chloro- and 2-amino-6-chloropurine (1 and 2, respectively) with 1-chloro-2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranose (3) gave the corresponding

  使用立体特异性钠盐糖基化方法已经完成了生物学上重要的2'-脱氧-6-硫鸟嘌呤（11），ara -6-硫鸟嘌呤（16）和ara G（17）的简单且高收率的合成。6-氯-和2-氨基-6-氯嘌呤（分别为1和2）的钠盐与1-氯-2-脱氧-3,5-二-O-（对甲苯甲酰基）-α-的糖基化D-赤型-五呋喃糖（3）给出了相应的N-9取代核苷，它们是具有β-端基异构体构型的主要产物（4和5，以及少量的N-7位置异构体（6和7）。在含有甲醇钠的甲醇中用硫化氢处理4，以93％的收率得到2'-deoxy-6-thioinosine（10）。类似地，将5以71％的产率转化为2'-脱氧-6-硫鸟苷（β-TGdR，11）。2的钠盐与1-氯-2,3,5-三-O-苄基-α-D-阿拉伯呋喃糖（8）的反应分别得到N-7和N-9糖基化产物13和9。9的脱苄基作用用三氯化硼在-78°下用62％的收率得到通用的中间体2-氨基-6-氯
• ZINCHENKO, A. I.;BARAJ, V. N.;MIXAJLOPULO, I. A., XIMIYA PRIROD. SOED.,(1989) N, S. 732-733
  作者：ZINCHENKO, A. I.、BARAJ, V. N.、MIXAJLOPULO, I. A.

  DOI：——

  日期：——
• Differences in kinetic properties of pure recombinant human and mouse deoxycytidine kinase
  作者：Magnus Johansson、Anna Karlsson

  DOI：10.1016/0006-2952(95)00129-n

  日期：1995.7

  Human and mouse deoxycytidine kinase (dCK) (EC 2.7.1.74) were cloned and expressed in Escherichia coli. Michaelis-Menten kinetics were determined for the purified enzymes with 2'-deoxycytidine (dCyd), 2'-deoxyadenosine (dAdo), 2-chloro-2'-deoxyadenosine (CdA), 2',3'-dideoxycytidine (ddCyd) and 9-beta-D-arabinofuranosylguanine (araG) as substrates and ATP and UTP as phosphate donors. Both human and mouse dCK showed highest affinity to dCyd with K-m values of 0.05-0.2 mu M. The anti-leukaemic compound CdA was the superior substrate of the nucleoside analogues tested. Both enzymes were able to efficiently utilize ATP and UTP as phosphate donors. However, the use of UTP instead of ATP as phosphate donor decreased K-m values for all substrates investigated. The kinetic properties of mouse and human dCK differed in that the human enzyme showed higher affinity for the substrates dAdo, CdA, ddCyd and araG. The human enzyme also showed higher affinity for ATP and UTP. The ability to phosphorylate dCyd was, however, similar for both human and mouse dCK. At physiological concentration of the feedback inhibitor dCTP, mouse dCK showed lower activity than human dCK for all substrates investigated.