[(2R,3S,5R)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl (2S)-2-[[(2S)-2-formamido-4-methylsulfanylbutanoyl]-methylamino]-4-methylpentanoate | 287731-59-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(2R,3S,5R)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl (2S)-2-[[(2S)-2-formamido-4-methylsulfanylbutanoyl]-methylamino]-4-methylpentanoate
• CAS: 287731-59-3
• 化学式: C₂₂H₃₃FN₄O₈S
• 分子量: 532.59
• InChiKey: RKPIHODTKBZJJN-NNPSNHGLSA-N

物化性质

• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  180
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl (2S)-2-[[(2S)-2-formamido-4-methylsulfanylbutanoyl]-methylamino]-4-methylpentanoate 在 phosphate buffer 、 peptide deformylase from E_. coli 作用下， 生成 (3S,6S)-6-Isobutyl-1-methyl-3-(2-methylsulfanyl-ethyl)-piperazine-2,5-dione 、 5-氟-2'-脱氧脲核苷
  参考文献：
  名称：

  Activation of antibacterial prodrugs by peptide deformylase

  摘要：

  5'-Dipeptidyl derivatives of 5-fluorodeoxyuridine (FdU) (1a-d) were synthesized. These compounds are biologically inactive but can be activated by peptide deformylase, which removes the N-terminal formyl group of the dipeptide, to release the active drug FdU via an intramolecular cyclization reaction. Because the deformylase is ubiquitous among bacteria but absent in mammalian cells, 1a-d provide a novel class of potential antibacterial agents. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00167-0
• 作为产物：
  描述：

  5-氟-2'-脱氧脲核苷 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 为溶剂， 生成 [(2R,3S,5R)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl (2S)-2-[[(2S)-2-formamido-4-methylsulfanylbutanoyl]-methylamino]-4-methylpentanoate
  参考文献：
  名称：

  Activation of antibacterial prodrugs by peptide deformylase

  摘要：

  5'-Dipeptidyl derivatives of 5-fluorodeoxyuridine (FdU) (1a-d) were synthesized. These compounds are biologically inactive but can be activated by peptide deformylase, which removes the N-terminal formyl group of the dipeptide, to release the active drug FdU via an intramolecular cyclization reaction. Because the deformylase is ubiquitous among bacteria but absent in mammalian cells, 1a-d provide a novel class of potential antibacterial agents. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00167-0

文献信息

• Activation of antibacterial prodrugs by peptide deformylase
  作者：Yaoming Wei、Dehua Pei

  DOI：10.1016/s0960-894x(00)00167-0

  日期：2000.5

  5'-Dipeptidyl derivatives of 5-fluorodeoxyuridine (FdU) (1a-d) were synthesized. These compounds are biologically inactive but can be activated by peptide deformylase, which removes the N-terminal formyl group of the dipeptide, to release the active drug FdU via an intramolecular cyclization reaction. Because the deformylase is ubiquitous among bacteria but absent in mammalian cells, 1a-d provide a novel class of potential antibacterial agents. (C) 2000 Elsevier Science Ltd. All rights reserved.