{1-Amino-3-[(2S,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethylsulfanyl]-propyl}-phosphonic acid

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: {1-Amino-3-[(2S,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethylsulfanyl]-propyl}-phosphonic acid
• 英文别名: 5'-[3-Amino-3-(dihydroxyphosphoryl)propylthio]-5'-deoxyadenosine；[1-amino-3-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methylsulfanyl]propyl]phosphonic acid
• 化学式: C₁₃H₂₁N₆O₆PS
• 分子量: 420.386
• InChiKey: URBLXQXQEIZOJN-XSMYZTMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.8
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  228
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  [3-[(3aS,4S,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethylsulfanyl]-1-(benzhydrylidene-amino)-propyl]-phosphonic acid diethyl ester 在 碘代三甲硅烷 作用下， 以 水 为溶剂， 以75%的产率得到{1-Amino-3-[(2S,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethylsulfanyl]-propyl}-phosphonic acid
  参考文献：
  名称：

  Synthesis of an α-Aminophosphonate Nucleoside as an Inhibitor of S-Adenosyl-l-Homocysteine Hydrolase

  摘要：

  A phosphonic acid analogue or S-adenosyl-L-homocysteine was prepared by a novel method and the epimeric mixture separated. Preliminary studies indicate that each epimer causes time-dependent inactivation of S-adenosyl-L-homocysteine hydrolase, however each presented distinct kinetic characteristics. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00789-2

文献信息

• Synthesis of an α-Aminophosphonate Nucleoside as an Inhibitor of S-Adenosyl-l-Homocysteine Hydrolase
  作者：Jennifer A Steere、Peter B Sampson、John F Honek

  DOI：10.1016/s0960-894x(01)00789-2

  日期：2002.2

  A phosphonic acid analogue or S-adenosyl-L-homocysteine was prepared by a novel method and the epimeric mixture separated. Preliminary studies indicate that each epimer causes time-dependent inactivation of S-adenosyl-L-homocysteine hydrolase, however each presented distinct kinetic characteristics. (C) 2002 Elsevier Science Ltd. All rights reserved.