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Metabolites 2018, 8(4), 80; https://doi.org/10.3390/metabo8040080

A Simple and Convenient Synthesis of Unlabeled and 13C-Labeled 3-(3-Hydroxyphenyl)-3-Hydroxypropionic Acid and Its Quantification in Human Urine Samples

1
Departments of Biological Sciences, University of Alberta, Edmonton, AB T6G 2E8, Canada
2
Departments of Computing Sciences, University of Alberta, Edmonton, AB T6G 2E8, Canada
3
National Institute of Nanotechnology, 11421 Saskatchewan Drive, Edmonton, AB T6G 2M9, Canada
*
Author to whom correspondence should be addressed.
Received: 5 October 2018 / Revised: 10 November 2018 / Accepted: 16 November 2018 / Published: 21 November 2018
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Abstract

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 13C 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. View Full-Text
Keywords: HPHPA; biomarker; isotopic labeling; sonication; Reformatsky reaction HPHPA; biomarker; isotopic labeling; sonication; Reformatsky reaction
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Khaniani, Y.; Lipfert, M.; Bhattacharyya, D.; Perez Pineiro, R.; Zheng, J.; Wishart, D.S. A Simple and Convenient Synthesis of Unlabeled and 13C-Labeled 3-(3-Hydroxyphenyl)-3-Hydroxypropionic Acid and Its Quantification in Human Urine Samples. Metabolites 2018, 8, 80.

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