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Metabolites. 2018 Nov 21;8(4). pii: E80. doi: 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.

Author information

1
Departments of Biological Sciences, University of Alberta, Edmonton, AB T6G 2E8, Canada. khaniani@ualberta.ca.
2
Departments of Biological Sciences, University of Alberta, Edmonton, AB T6G 2E8, Canada. lipfert@ualberta.ca.
3
Departments of Biological Sciences, University of Alberta, Edmonton, AB T6G 2E8, Canada. dbhattac@ualberta.ca.
4
Departments of Biological Sciences, University of Alberta, Edmonton, AB T6G 2E8, Canada. rpp_10400@yahoo.com.
5
Departments of Biological Sciences, University of Alberta, Edmonton, AB T6G 2E8, Canada. jiamin3@ualberta.ca.
6
Departments of Biological Sciences, University of Alberta, Edmonton, AB T6G 2E8, Canada. dwishart@ualberta.ca.
7
Departments of Computing Sciences, University of Alberta, Edmonton, AB T6G 2E8, Canada. dwishart@ualberta.ca.
8
National Institute of Nanotechnology, 11421 Saskatchewan Drive, Edmonton, AB T6G 2M9, Canada. dwishart@ualberta.ca.

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.

KEYWORDS:

HPHPA; Reformatsky reaction; biomarker; isotopic labeling; sonication

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