3',5'-di-O-benzoyl-2'-deoxy-β-L-N²-palmitoylguanosine | 144224-72-6

• 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-benzoyl-2'-deoxy-β-L-N²-palmitoylguanosine
• 英文别名: [(2S,3R,5S)-3-benzoyloxy-5-[2-(hexadecanoylamino)-6-oxo-1H-purin-9-yl]oxolan-2-yl]methyl benzoate
• CAS: 144224-72-6；144224-73-7
• 化学式: C₄₀H₅₁N₅O₇
• 分子量: 713.874
• InChiKey: VJWFURYVGVBYJD-AXIPTUPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  52
• 可旋转键数：
  23
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  150
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3',5'-di-O-benzoyl-2'-deoxy-β-L-N²-palmitoylguanosine 在 吡啶 、 ammonium hydroxide 作用下， 反应 24.0h， 以76%的产率得到2'-deoxyguanosine
  参考文献：
  名称：

  L-Thymidine is phosphorylated by herpes simplex virus type 1 thymidine kinase and inhibits viral growth

  摘要：

  We have demonstrated that herpes simplex 1 (HSV1) thymidine kinase (TK) shows no stereospecificity for D- and L-beta-nucleosides. In vitro, L enantiomers are not recognized by human TK, but function as specific substrates for the viral enzyme in the order: L-thymidine (L-T) much greater than 2'-deoxy-L-guanosine (L-dG) > 2'-deoxy-L-uridine (L-dU) > 2'-deoxy-L-cytidine (L-dC) > 2'-deoxy-L-adenosine (L-dA). HSV1 TK phosphorylates both thymidine enantiomers to their corresponding monophosphates with identical efficiency and the K(i) of L-T (2 muM) is almost identical to the K(m) for the natural substrate D-T (2.8 muM). The L enantiomer reduces the incorporation of exogenous [H-3]T into cellular DNA in HeLa TK-/HSV1 TK+ but not in wild-type HeLa cells, without affecting RNA, protein synthesis, cell growth, and viability. L-T markedly reduces HSV1 multiplication in HeLa cells. Our observations could lead to the development of a novel class of antiviral drugs characterized by low toxicity.

  DOI：

  10.1021/jm00100a029
• 作为产物：
  描述：

  N²-palmytoylguanine 、 3',5'-dibenzoyl-2'-deoxy-β-L-uridine 在 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 作用下， 生成 、 [(2S,3R,5R)-3-benzoyloxy-5-[2-(hexadecanoylamino)-6-oxo-1H-purin-9-yl]oxolan-2-yl]methyl benzoate 、 3',5'-di-O-benzoyl-2'-deoxy-β-L-N²-palmitoylguanosine
  参考文献：
  名称：

  L-Thymidine is phosphorylated by herpes simplex virus type 1 thymidine kinase and inhibits viral growth

  摘要：

  We have demonstrated that herpes simplex 1 (HSV1) thymidine kinase (TK) shows no stereospecificity for D- and L-beta-nucleosides. In vitro, L enantiomers are not recognized by human TK, but function as specific substrates for the viral enzyme in the order: L-thymidine (L-T) much greater than 2'-deoxy-L-guanosine (L-dG) > 2'-deoxy-L-uridine (L-dU) > 2'-deoxy-L-cytidine (L-dC) > 2'-deoxy-L-adenosine (L-dA). HSV1 TK phosphorylates both thymidine enantiomers to their corresponding monophosphates with identical efficiency and the K(i) of L-T (2 muM) is almost identical to the K(m) for the natural substrate D-T (2.8 muM). The L enantiomer reduces the incorporation of exogenous [H-3]T into cellular DNA in HeLa TK-/HSV1 TK+ but not in wild-type HeLa cells, without affecting RNA, protein synthesis, cell growth, and viability. L-T markedly reduces HSV1 multiplication in HeLa cells. Our observations could lead to the development of a novel class of antiviral drugs characterized by low toxicity.

  DOI：

  10.1021/jm00100a029

文献信息

• L-Thymidine is phosphorylated by herpes simplex virus type 1 thymidine kinase and inhibits viral growth
  作者：Silvio Spadari、Giovanni Maga、Federico Focher、Giovanni Ciarrocchi、Roberto Manservigi、Federico Arcamone、Massimo Capobianco、Antonio Carcuro、Francesco Colonna

  DOI：10.1021/jm00100a029

  日期：1992.10

  We have demonstrated that herpes simplex 1 (HSV1) thymidine kinase (TK) shows no stereospecificity for D- and L-beta-nucleosides. In vitro, L enantiomers are not recognized by human TK, but function as specific substrates for the viral enzyme in the order: L-thymidine (L-T) much greater than 2'-deoxy-L-guanosine (L-dG) > 2'-deoxy-L-uridine (L-dU) > 2'-deoxy-L-cytidine (L-dC) > 2'-deoxy-L-adenosine (L-dA). HSV1 TK phosphorylates both thymidine enantiomers to their corresponding monophosphates with identical efficiency and the K(i) of L-T (2 muM) is almost identical to the K(m) for the natural substrate D-T (2.8 muM). The L enantiomer reduces the incorporation of exogenous [H-3]T into cellular DNA in HeLa TK-/HSV1 TK+ but not in wild-type HeLa cells, without affecting RNA, protein synthesis, cell growth, and viability. L-T markedly reduces HSV1 multiplication in HeLa cells. Our observations could lead to the development of a novel class of antiviral drugs characterized by low toxicity.