(R)-3-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-4-hydroxybutylphosphonic acid monophosphate | 266344-94-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (R)-3-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-4-hydroxybutylphosphonic acid monophosphate
• 英文别名: (R)-ganciclovir phosphonate monophosphate；[(3R)-3-[(2-amino-6-oxo-1H-purin-9-yl)methoxy]-4-hydroxybutyl]-phosphonooxyphosphinic acid
• CAS: 266344-94-9
• 化学式: C₁₀H₁₇N₅O₉P₂
• 分子量: 413.221
• InChiKey: YAPJPYOLJVSZHC-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.4
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  219
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (R)-3-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-4-hydroxybutylphosphonic acid monophosphate 在 creatine phosphate 、 creatine kinase (EC 2.7.3.2) from rabbit muscle 、 magnesium acetate 作用下， 以 水 为溶剂， 反应 24.0h， 以85%的产率得到(R)-3-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-4-hydroxybutylphosphonic acid dinophosphate
  参考文献：
  名称：

  Phosphorylation of Ganciclovir Phosphonate by Cellular GMP Kinase Determines the Stereoselectivity of Anti-Human Cytomegalovirus Activity

  摘要：

  A racemic mixture of ganciclovir phosphonate was resolved by stereoselective phosphorylation using GMP kinase. The R-enantiomer of ganciclovir phosphonate was active against human cytomegalovirus but the S-enantiomer was less active. We show that enantiomeric selectivity of antiviral activity for ganciclovir phosphonate was conferred by stereoselective phosphorylations by mammalian enzymes, not by stereoslective inhibition of DNA polymerase from human cytomegalovirus.

  DOI：

  10.1080/15257770008033013
• 作为产物：
  描述：

  [(3R)-3-[(2-氨基-6-氧代-3H-嘌呤-9-基)甲氧基]-4-羟基丁基]膦酸 在 GMP kinase from numan red blood cells 作用下， 生成 (R)-3-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-4-hydroxybutylphosphonic acid monophosphate
  参考文献：
  名称：

  Phosphorylation of Ganciclovir Phosphonate by Cellular GMP Kinase Determines the Stereoselectivity of Anti-Human Cytomegalovirus Activity

  摘要：

  A racemic mixture of ganciclovir phosphonate was resolved by stereoselective phosphorylation using GMP kinase. The R-enantiomer of ganciclovir phosphonate was active against human cytomegalovirus but the S-enantiomer was less active. We show that enantiomeric selectivity of antiviral activity for ganciclovir phosphonate was conferred by stereoselective phosphorylations by mammalian enzymes, not by stereoslective inhibition of DNA polymerase from human cytomegalovirus.

  DOI：

  10.1080/15257770008033013

文献信息

• Phosphorylation of Ganciclovir Phosphonate by Cellular GMP Kinase Determines the Stereoselectivity of Anti-Human Cytomegalovirus Activity
  作者：Wayne H. Miller、Lilia M. Beauchamp、Eric Meade、John E. Reardon、Karen K. Biron、Albert A. Smith、Charles A. Goss、Richard L. Miller

  DOI：10.1080/15257770008033013

  日期：2000.1

  A racemic mixture of ganciclovir phosphonate was resolved by stereoselective phosphorylation using GMP kinase. The R-enantiomer of ganciclovir phosphonate was active against human cytomegalovirus but the S-enantiomer was less active. We show that enantiomeric selectivity of antiviral activity for ganciclovir phosphonate was conferred by stereoselective phosphorylations by mammalian enzymes, not by stereoslective inhibition of DNA polymerase from human cytomegalovirus.