对乙酰氨基马尿酸甲酯 | 64480-74-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 对乙酰氨基马尿酸甲酯
• 英文名称: p-acetaminohippuric acid methyl ester
• 英文别名: Methyl 2-[(4-acetamidophenyl)formamido]acetate；methyl 2-[(4-acetamidobenzoyl)amino]acetate
• CAS: 64480-74-6
• 化学式: C₁₂H₁₄N₂O₄
• mdl: MFCD01195276
• 分子量: 250.254
• InChiKey: TUGFYHINOTVYSA-UHFFFAOYSA-N

物化性质

• 沸点：
  516.3±35.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  对乙酰氨基马尿酸甲酯 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 4-乙酰基氨马尿酸
  参考文献：
  名称：

  Biomimetic Catalysis of Intermodular Aminoacyl Transfer

  摘要：

  Intermodular aminoacyl transfer is the fundamental bond-forming reaction in the biosynthesis of polypeptides by ribosomes and nonribosomal peptide synthetases (NRPS). Here we report the design and functional characterizations of short synthetic alpha-helical peptides that mimic the aminoacyl loading and intermodular aminoacyl transfer steps of NRPS with aminolysis rate enhancements in neutral aqueous solutions of up to 5400-fold (k(cat)/k(uncat)). The catalysts operate as noncovalently associated peptide assemblies with composite active sites fashioned at the interface between helical subunits. Following the substrate loading at the active site cysteine, the juxtaposition of the resulting aminoacyl thiolester and the nucleophilic amine of the acyl acceptor moiety gives rise to high effective concentrations (up to 54 M) that facilitate interhelical aminoacyl transfer with rates typically exceeding 10(-4) sec(-1). Moreover, studies based on homo- and heteromeric assemblies, active site amino acid substitutions, kinetic analysis, and reaction modeling indicate that the de novo designed supramolecular catalysts reported herein exhibit some of the basic characteristics of natural enzymes, including precise positioning and pK(a) modulation of active site residues, covalent catalysis, and multiple product turnovers.

  DOI：

  10.1021/ja067124h
• 作为产物：
  描述：

  对氨基马尿酸 在 sodium hydroxide 作用下， 以 甲醇 、 乙醚 、 乙醇 为溶剂， 反应 1.17h， 生成 对乙酰氨基马尿酸甲酯
  参考文献：
  名称：

  在雄性F344大鼠中口服N，N-二甲基-对甲苯胺的尿代谢产物的鉴定。

  摘要：

  研究了雄性F344大鼠中口服N，N-二甲基对甲苯胺（DMPT）的代谢。大鼠尿代谢产物谱通过分析型反相高效液相色谱法（HPLC）测定。通过固相萃取（SPE）和制备型HPLC方法观察，分离和纯化了四个放射性标记的峰。这4个峰被鉴定为对-（N-乙酰羟氨基）马尿酸（M1），DMPT N-氧化物（M2），N-甲基-对甲苯胺（M3）和母体DMPT。代谢物M1和M2通过光谱和光谱方法进行鉴定，包括从液相色谱/质谱和气相色谱/质谱以及核磁共振光谱的化学分析中鉴定质量碎片模式。通过与合成标准品进行比较来完成代谢物M2的结构确认。通过分别将它们的HPLC保留时间和质量裂解模式与N-甲基-对甲苯胺和DMPT的真实标准品进行比较，确定了M3和DMPT峰。DMPT代谢与报道的N，N-二甲基苯胺相似。

  DOI：

  10.1080/15287390701206176

文献信息

• Biomimetic Catalysis of Intermodular Aminoacyl Transfer
  作者：Keith M. Wilcoxen、Luke J. Leman、Dana A. Weinberger、Zheng-Zheng Huang、M. Reza Ghadiri

  DOI：10.1021/ja067124h

  日期：2007.1.1

  Intermodular aminoacyl transfer is the fundamental bond-forming reaction in the biosynthesis of polypeptides by ribosomes and nonribosomal peptide synthetases (NRPS). Here we report the design and functional characterizations of short synthetic alpha-helical peptides that mimic the aminoacyl loading and intermodular aminoacyl transfer steps of NRPS with aminolysis rate enhancements in neutral aqueous solutions of up to 5400-fold (k(cat)/k(uncat)). The catalysts operate as noncovalently associated peptide assemblies with composite active sites fashioned at the interface between helical subunits. Following the substrate loading at the active site cysteine, the juxtaposition of the resulting aminoacyl thiolester and the nucleophilic amine of the acyl acceptor moiety gives rise to high effective concentrations (up to 54 M) that facilitate interhelical aminoacyl transfer with rates typically exceeding 10(-4) sec(-1). Moreover, studies based on homo- and heteromeric assemblies, active site amino acid substitutions, kinetic analysis, and reaction modeling indicate that the de novo designed supramolecular catalysts reported herein exhibit some of the basic characteristics of natural enzymes, including precise positioning and pK(a) modulation of active site residues, covalent catalysis, and multiple product turnovers.
• Identification of Urinary Metabolites of Orally Administered<i>N</i>,<i>N</i>-Dimethyl-<i>p</i>-Toluidine in Male F344 Rats∗
  作者：Nam-Cheol Kim、Katayoon Ghanbari、Dean A. Kracko、Waylon M. Weber、Jacob D. McDonald、Kelly J. Dix

  DOI：10.1080/15287390701206176

  日期：2007.4.11

  The metabolism of orally administered N,N-dimethyl-p-toluidine (DMPT) in male F344 rats was investigated. The rat urinary metabolite profile was determined by analytical reverse-phase high performance liquid chromatography (HPLC). Four radiolabeled peaks were observed, isolated, and purified by solid-phase extraction (SPE) and preparative HPLC methods. The 4 peaks were identified as p-(N-acetylhydroxyamino)hippuric

  研究了雄性F344大鼠中口服N，N-二甲基对甲苯胺（DMPT）的代谢。大鼠尿代谢产物谱通过分析型反相高效液相色谱法（HPLC）测定。通过固相萃取（SPE）和制备型HPLC方法观察，分离和纯化了四个放射性标记的峰。这4个峰被鉴定为对-（N-乙酰羟氨基）马尿酸（M1），DMPT N-氧化物（M2），N-甲基-对甲苯胺（M3）和母体DMPT。代谢物M1和M2通过光谱和光谱方法进行鉴定，包括从液相色谱/质谱和气相色谱/质谱以及核磁共振光谱的化学分析中鉴定质量碎片模式。通过与合成标准品进行比较来完成代谢物M2的结构确认。通过分别将它们的HPLC保留时间和质量裂解模式与N-甲基-对甲苯胺和DMPT的真实标准品进行比较，确定了M3和DMPT峰。DMPT代谢与报道的N，N-二甲基苯胺相似。