methyl 3-[3-[[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxypropoxymethyl-ethoxyphosphoryl]-2-methylpropanoate | 356785-87-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: methyl 3-[3-[[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxypropoxymethyl-ethoxyphosphoryl]-2-methylpropanoate
• CAS: 356785-87-0
• 化学式: C₂₀H₃₅N₂O₁₇P₃
• 分子量: 668.422
• InChiKey: PXAHJEMVMPPCFO-NZXJZFJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  42
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  263
• 氢给体数：
  5
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  methyl 3-[3-[[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxypropoxymethyl-ethoxyphosphoryl]-2-methylpropanoate 在 lithium hydroxide 作用下， 反应 2.0h， 以88%的产率得到3-[3-[[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxypropoxymethyl-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：

  (3-Benzyloxy-propoxymethyl)-phosphinic acid ethyl ester 在 platinum(IV) oxide 、 palladium on activated charcoal 吡啶 、 四氮唑 、 4-二甲氨基吡啶 、 三甲基氯硅烷 、 TEA 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 methyl 3-[3-[[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxypropoxymethyl-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

文献信息

• Inhibitors of the bacterial cell wall biosynthesis enzyme MurC
  作者：Folkert Reck、Stephen Marmor、Stewart Fisher、Mark A. Wuonola

  DOI：10.1016/s0960-894x(01)00251-7

  日期：2001.6

  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.