bis(p-nitrobenzyl) 6-[N-(p-nitrobenzyloxycarbonyl)glycyl-L-α-aminopimelyl]aminopenicillanate | 726201-89-4

• 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: bis(p-nitrobenzyl) 6-[N-(p-nitrobenzyloxycarbonyl)glycyl-L-α-aminopimelyl]aminopenicillanate
• CAS: 726201-89-4
• 化学式: C₃₉H₄₁N₇O₁₅S
• 分子量: 879.858
• InChiKey: MAQBXSBONWZRJU-DEBPNWLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  62.0
• 可旋转键数：
  20.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  298.86
• 氢给体数：
  3.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  bis(p-nitrobenzyl) 6-[N-(p-nitrobenzyloxycarbonyl)glycyl-L-α-aminopimelyl]aminopenicillanate 在 palladium on activated charcoal 氢气 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 2.5h， 以14.4 mg的产率得到6-(glycyl-L-α-aminopimelyl)aminopenicillananic acid
  参考文献：
  名称：

  The Perfect Penicillin? Inhibition of a Bacterial DD-Peptidase by Peptidoglycan-Mimetic β-Lactams

  摘要：

  6-(Glycyl-l-alpha-aminopimelyl)-aminopenicillanic acid and 7-(glycyl-l-alpha-aminopimelyl)-aminocephalosporanic acid have been synthesized as Streptomyces sp. peptidoglycan-mimetic beta-lactams. These compounds inactivate the Streptomyces R61 DD-peptidase with rate constants of 1.5 x 107 s-1 M-1 and 5.6 x 105 s-1 M-1, respectively. The former compound is thus the most effective beta-lactam inhibitor of a DD-peptidase yet described. The analogous d-alanyl-d-alanine peptide has previously been shown to react with this enzyme with comparable efficiency, kcat/Km = 8.7 x 106 s-1 M-1. These results show that, in this case at least, incorporation of a peptidoglycan-mimetic side chain into a beta-lactam greatly enhances its activity as a DD-peptidase inhibitor. This result has interesting implications for beta-lactam design.

  DOI：

  10.1021/ja048850s
• 作为产物：
  描述：

  N-(p-nitrobenzyloxycarbonyl)glycyl-L-α-aminopimelic acid 在 1-羟基苯并三唑 、 二环己胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.08h， 生成 bis(p-nitrobenzyl) 6-[N-(p-nitrobenzyloxycarbonyl)glycyl-L-α-aminopimelyl]aminopenicillanate
  参考文献：
  名称：

  The Perfect Penicillin? Inhibition of a Bacterial DD-Peptidase by Peptidoglycan-Mimetic β-Lactams

  摘要：

  6-(Glycyl-l-alpha-aminopimelyl)-aminopenicillanic acid and 7-(glycyl-l-alpha-aminopimelyl)-aminocephalosporanic acid have been synthesized as Streptomyces sp. peptidoglycan-mimetic beta-lactams. These compounds inactivate the Streptomyces R61 DD-peptidase with rate constants of 1.5 x 107 s-1 M-1 and 5.6 x 105 s-1 M-1, respectively. The former compound is thus the most effective beta-lactam inhibitor of a DD-peptidase yet described. The analogous d-alanyl-d-alanine peptide has previously been shown to react with this enzyme with comparable efficiency, kcat/Km = 8.7 x 106 s-1 M-1. These results show that, in this case at least, incorporation of a peptidoglycan-mimetic side chain into a beta-lactam greatly enhances its activity as a DD-peptidase inhibitor. This result has interesting implications for beta-lactam design.

  DOI：

  10.1021/ja048850s