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

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Departments of Biological Sciences, University of Alberta, Edmonton, AB T6G 2E8, Canada
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Departments of Computing Sciences, University of Alberta, Edmonton, AB T6G 2E8, Canada
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National Institute of Nanotechnology, 11421 Saskatchewan Drive, Edmonton, AB T6G 2M9, Canada
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Author to whom correspondence should be addressed.
Metabolites 2018, 8(4), 80; https://doi.org/10.3390/metabo8040080
Received: 5 October 2018 / Revised: 10 November 2018 / Accepted: 16 November 2018 / Published: 21 November 2018
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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MDPI and ACS Style

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. https://doi.org/10.3390/metabo8040080

AMA Style

Khaniani Y, Lipfert M, Bhattacharyya D, Perez Pineiro R, Zheng J, Wishart DS. 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(4):80. https://doi.org/10.3390/metabo8040080

Chicago/Turabian Style

Khaniani, Yeganeh, Matthias Lipfert, Dipanjan Bhattacharyya, Rolando Perez Pineiro, Jiamin Zheng, and David S. Wishart 2018. "A Simple and Convenient Synthesis of Unlabeled and 13C-Labeled 3-(3-Hydroxyphenyl)-3-Hydroxypropionic Acid and Its Quantification in Human Urine Samples" Metabolites 8, no. 4: 80. https://doi.org/10.3390/metabo8040080

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