[(2R,3S,5R)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl 2-[[(2S)-2-formamido-4-methylsulfanylbutanoyl]amino]-2-methylpropanoate | 287731-60-6

• 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 2-[[(2S)-2-formamido-4-methylsulfanylbutanoyl]amino]-2-methylpropanoate
• CAS: 287731-60-6
• 化学式: C₁₉H₂₇FN₄O₈S
• 分子量: 490.51
• InChiKey: GTDYOEPHYBTHGR-IGQOVBAYSA-N

物化性质

• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  189
• 氢给体数：
  4
• 氢受体数：
  10

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	t-Boc-Aib-FudR	287731-67-3	C18H26FN3O8	431.418
  ——	Aib-FudR	502847-16-7	C13H18FN3O6	331.301
  5-氟-2'-脱氧脲核苷	5-Fluoro-2'-deoxyuridine	50-91-9	C9H11FN2O5	246.195

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  5-氟-2'-脱氧脲核苷	5-Fluoro-2'-deoxyuridine	50-91-9	C9H11FN2O5	246.195

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 2-[[(2S)-2-formamido-4-methylsulfanylbutanoyl]amino]-2-methylpropanoate 在 phosphate buffer 、 peptide deformylase from E_. coli 作用下， 生成 (S)-3,3-Dimethyl-6-(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 TEA 、 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 、 二氯甲烷 为溶剂， 生成 [(2R,3S,5R)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl 2-[[(2S)-2-formamido-4-methylsulfanylbutanoyl]amino]-2-methylpropanoate
  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.