4-[2-((S)-5-Acetylamino-1-{(S)-1-[benzyloxy-((R)-1-benzyloxycarbonyl-ethoxy)-phosphoryl]-ethylcarbamoyl}-pentylcarbamoyl)-ethylcarbamoyl]-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester | 444188-75-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: 4-[2-((S)-5-Acetylamino-1-{(S)-1-[benzyloxy-((R)-1-benzyloxycarbonyl-ethoxy)-phosphoryl]-ethylcarbamoyl}-pentylcarbamoyl)-ethylcarbamoyl]-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester
• CAS: 444188-75-4
• 化学式: C₃₉H₅₂N₅O₁₃P
• 分子量: 829.841
• InChiKey: HUDYUQMYXWTJPY-KTVPMKSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  58.0
• 可旋转键数：
  25.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  241.91
• 氢给体数：
  4.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  4-[2-((S)-5-Acetylamino-1-{(S)-1-[benzyloxy-((R)-1-benzyloxycarbonyl-ethoxy)-phosphoryl]-ethylcarbamoyl}-pentylcarbamoyl)-ethylcarbamoyl]-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 4-[2-((S)-5-Acetylamino-1-{(S)-1-[((R)-1-carboxy-ethoxy)-hydroxy-phosphoryl]-ethylcarbamoyl}-pentylcarbamoyl)-ethylcarbamoyl]-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester
  参考文献：
  名称：

  Antibody-catalyzed cleavage of the d -Ala- d -Lac depsipeptide: An immunological approach to the problem of vancomycin resistance

  摘要：

  Vancomyein resistance is currently a major healthcare problem. The development of a catalytic monoclonal antibody (mAb) that hydrolyzes the D-Ala-D-Lac depsipeptide provides a potentially novel antibiotic strategy. A phosphonate hapten design was used to program antibody catalysis. The characteristics of the hapten were shown to be important for obtaining a viable immune response and several catalytic mAbs that cleave a peptidoglycan model substrate. The best mAb afforded a > 500-fold rate enhancement over background. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00047-1
• 作为产物：
  描述：

  (R)-2-{[(S)-1-((S)-6-Acetylamino-2-amino-hexanoylamino)-ethyl]-benzyloxy-phosphinoyloxy}-propionic acid benzyl ester 在 N-甲基吗啉 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 4-[2-((S)-5-Acetylamino-1-{(S)-1-[benzyloxy-((R)-1-benzyloxycarbonyl-ethoxy)-phosphoryl]-ethylcarbamoyl}-pentylcarbamoyl)-ethylcarbamoyl]-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester
  参考文献：
  名称：

  Antibody-catalyzed cleavage of the d -Ala- d -Lac depsipeptide: An immunological approach to the problem of vancomycin resistance

  摘要：

  Vancomyein resistance is currently a major healthcare problem. The development of a catalytic monoclonal antibody (mAb) that hydrolyzes the D-Ala-D-Lac depsipeptide provides a potentially novel antibiotic strategy. A phosphonate hapten design was used to program antibody catalysis. The characteristics of the hapten were shown to be important for obtaining a viable immune response and several catalytic mAbs that cleave a peptidoglycan model substrate. The best mAb afforded a > 500-fold rate enhancement over background. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00047-1