Khaniani Yeganeh, Lipfert Matthias, Bhattacharyya Dipanjan, Perez Pineiro Rolando, Zheng Jiamin, Wishart David S
Departments of Biological Sciences, University of Alberta, Edmonton, AB T6G 2E8, Canada.
Departments of Computing Sciences, University of Alberta, Edmonton, AB T6G 2E8, Canada.
Metabolites. 2018 Nov 21;8(4):80. doi: 10.3390/metabo8040080.
An improved method to synthesize the highly abundant and biomedically important urinary metabolite 3-(3-hydroxyphenyl)-3-hydroxypropionic acid (HPHPA) is reported. The modified protocol is based on an indium-mediated sonochemical Reformatsky reaction. The synthesis is a simple two-step route as opposed to a complex four-step route previously reported in the literature that requires specialized equipment, flammable materials, and high-pressure reaction vessels. The described procedure also provides an expedient route to prepare a C isotopically labeled HPHPA that can be used as a standard for quantitative LC-MS analysis. This report also illustrates how the synthesized metabolite standard was used to detect and accurately quantify its presence in human urine samples using both NMR and LC-MS techniques.
报道了一种合成高丰度且具有重要生物医学意义的尿液代谢物3-(3-羟基苯基)-3-羟基丙酸（HPHPA）的改进方法。改进后的方案基于铟介导的声化学Reformatsky反应。该合成是一条简单的两步路线，而不是文献中先前报道的需要专门设备、易燃材料和高压反应容器的复杂四步路线。所描述的方法还提供了一条便捷的路线来制备碳同位素标记的HPHPA，其可作为定量液相色谱-质谱分析的标准品。本报告还说明了如何使用合成的代谢物标准品，通过核磁共振（NMR）和液相色谱-质谱（LC-MS）技术检测并准确定量其在人类尿液样本中的存在。
