3',5'-di-O-methyl-2'-deoxyadenosine | 130999-21-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 3',5'-di-O-methyl-2'-deoxyadenosine
• 英文别名: 9-[(2R,4S,5R)-4-methoxy-5-(methoxymethyl)oxolan-2-yl]purin-6-amine
• CAS: 130999-21-2
• 化学式: C₁₂H₁₇N₅O₃
• 分子量: 279.299
• InChiKey: PFDUWMYZSIIWRZ-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  97.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  [Bis-(4-methoxy-phenyl)-phenyl-methyl]-[9-((2R,4S,5R)-4-methoxy-5-methoxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-amine 在 三氯乙酸 作用下， 以 氯仿 为溶剂， 以85%的产率得到3',5'-di-O-methyl-2'-deoxyadenosine
  参考文献：
  名称：

  Unimolecular depurination of protonated deoxyribonucleosides in the gas phase: A fast atom bombardment tandem mass spectrometric investigation

  摘要：

  AbstractThe spontaneous or collision‐induced unimolecular dissociations of base‐protonated 2′‐deoxyribonucleosides afford, in the gas phase and in the absence of solvent, high yields of protonated nucleobases. The release of neutral bases corresponds to a high‐energy reaction path and does not compete with the formation of the protonated bases. A determinant solvent effect has to be invoked to explain the opposite behaviour, which is exhibited by the same precursors, dissociating unimolecularly, in aqueous acidic solution.

  DOI：

  10.1002/oms.1210250906

文献信息

• Substrate/Inhibitor Properties of Human Deoxycytidine Kinase (dCK) and Thymidine Kinases (Tk1 And Tk2) Towards the Sugar Moiety of Nucleosides, Including O′-Alkyl Analogues
  作者：Borys Kierdaszuk、Krzysztof Krawiec、Zygmunt Kazimierczuk、Ulla Jacobsson、Nils G. Johansson、Birgitte Munch-petersen、Staffan Eriksson、David Shugar

  DOI：10.1080/07328319908044850

  日期：1999.8

  deoxycytidine kinase (dCK) and thymidine kinases (tetrameric high-affinity form of TK1, and TK2) from human leukemic spleen. In particular, the analogues included the mono- and di-O'-methyl derivatives of dC, dU and dA, syntheses of which are described. In general, purine nucleosides with modified sugar rings were feebler substrates than the corresponding cytosine analogues. Sugar-modified analogues of dU were

  已经检查了具有修饰的糖部分的核苷类似物对人类白血病脾脏的高度纯化的脱氧胞苷激酶（dCK）和胸苷激酶（TK1和TK2的四聚体高亲和力形式）的底物/抑制剂特异性。特别地，类似物包括dC，dU和dA的单-和二-O'-甲基衍生物，描述了它们的合成。通常，具有修饰的糖环的嘌呤核苷比相应的胞嘧啶类似物更弱。糖修饰的dU类似物也是TK1和TK2的底物相对较弱，但还是相当好的抑制剂，与TK2相比，Ki值通常低于TK1。TK1和TK2之间的出色区分是3'-己酰氨基-2'，3'-二脱氧胸苷，TK1的Ki约为600 microM，Ki约为0。TK2为1 microM。3'-OMe-dC是dCK优于其5'-O-甲基同类物的抑制剂，与作为质子受体的（3'）-OH或（3'）-OMe的氧可能参与氢键结合与酶。令人惊讶的是，alpha-dT是TK1和TK2的良好底物，TK1和TK2的Ki值分别为120和30 microM