methyl 3-[[(2R,3S,4R,5R,6R)-5-acetamido-3-acetyloxy-2-(acetyloxymethyl)-6-[[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxyoxan-4-yl]oxymethyl-ethoxyphosphoryl]-2-methylpropanoate | 356785-93-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: methyl 3-[[(2R,3S,4R,5R,6R)-5-acetamido-3-acetyloxy-2-(acetyloxymethyl)-6-[[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxyoxan-4-yl]oxymethyl-ethoxyphosphoryl]-2-methylpropanoate
• CAS: 356785-93-8
• 化学式: C₂₉H₄₆N₃O₂₃P₃
• 分子量: 897.612
• InChiKey: KWORXFWPTCLICO-UEARRXHMSA-N

物化性质

• 密度：
  1.57±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.4
• 重原子数：
  58
• 可旋转键数：
  23
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  354
• 氢给体数：
  6
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  methyl 3-[[(2R,3S,4R,5R,6R)-5-acetamido-3-acetyloxy-2-(acetyloxymethyl)-6-[[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxyoxan-4-yl]oxymethyl-ethoxyphosphoryl]-2-methylpropanoate 在 sodium hydroxide 作用下， 反应 1.5h， 以79%的产率得到3-[[(2R,3R,4R,5S,6R)-3-acetamido-2-[[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxymethyl-hydroxyphosphoryl]-2-methylpropanoic acid
  参考文献：
  名称：

  Inhibitors of the bacterial cell wall biosynthesis enzyme MurC

  摘要：

  A series of phosphinate transition-state analogues of the L-alanine adding enzyme (MurC) of bacterial peptidoglycan biosynthesis was prepared and tested as inhibitors of the Escherichia coli enzyme. Compound 4 was identified as a potent inhibitor of MurC from Escherichia coli with an IC50 Of 49 nM. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00251-7
• 作为产物：
  描述：

  benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 在 platinum(IV) oxide 、 palladium on activated charcoal 吡啶 、 正丁基锂 、 三甲基氯硅烷 、 TEA 、 水 、 氢气 、 sodium hydride 、 C.I.酸性橙108 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 296.61h， 生成 methyl 3-[[(2R,3S,4R,5R,6R)-5-acetamido-3-acetyloxy-2-(acetyloxymethyl)-6-[[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxyoxan-4-yl]oxymethyl-ethoxyphosphoryl]-2-methylpropanoate
  参考文献：
  名称：

  Inhibitors of the bacterial cell wall biosynthesis enzyme MurC

  摘要：

  A series of phosphinate transition-state analogues of the L-alanine adding enzyme (MurC) of bacterial peptidoglycan biosynthesis was prepared and tested as inhibitors of the Escherichia coli enzyme. Compound 4 was identified as a potent inhibitor of MurC from Escherichia coli with an IC50 Of 49 nM. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00251-7