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A Simple and Convenient Synthesis of Unlabeled and (13)C-Labeled 3-(3-Hydroxyphenyl)-3-Hydroxypropionic Acid and Its Quantification in Human Urine Samples
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 oppo...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6316614/ https://www.ncbi.nlm.nih.gov/pubmed/30469313 http://dx.doi.org/10.3390/metabo8040080 |
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author | Khaniani, Yeganeh Lipfert, Matthias Bhattacharyya, Dipanjan Perez Pineiro, Rolando Zheng, Jiamin Wishart, David S. |
author_facet | Khaniani, Yeganeh Lipfert, Matthias Bhattacharyya, Dipanjan Perez Pineiro, Rolando Zheng, Jiamin Wishart, David S. |
author_sort | Khaniani, Yeganeh |
collection | PubMed |
description | 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 (13)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. |
format | Online Article Text |
id | pubmed-6316614 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-63166142019-01-10 A Simple and Convenient Synthesis of Unlabeled and (13)C-Labeled 3-(3-Hydroxyphenyl)-3-Hydroxypropionic Acid and Its Quantification in Human Urine Samples Khaniani, Yeganeh Lipfert, Matthias Bhattacharyya, Dipanjan Perez Pineiro, Rolando Zheng, Jiamin Wishart, David S. Metabolites Article 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 (13)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. MDPI 2018-11-21 /pmc/articles/PMC6316614/ /pubmed/30469313 http://dx.doi.org/10.3390/metabo8040080 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Khaniani, Yeganeh Lipfert, Matthias Bhattacharyya, Dipanjan Perez Pineiro, Rolando Zheng, Jiamin Wishart, David S. A Simple and Convenient Synthesis of Unlabeled and (13)C-Labeled 3-(3-Hydroxyphenyl)-3-Hydroxypropionic Acid and Its Quantification in Human Urine Samples |
title | A Simple and Convenient Synthesis of Unlabeled and (13)C-Labeled 3-(3-Hydroxyphenyl)-3-Hydroxypropionic Acid and Its Quantification in Human Urine Samples |
title_full | A Simple and Convenient Synthesis of Unlabeled and (13)C-Labeled 3-(3-Hydroxyphenyl)-3-Hydroxypropionic Acid and Its Quantification in Human Urine Samples |
title_fullStr | A Simple and Convenient Synthesis of Unlabeled and (13)C-Labeled 3-(3-Hydroxyphenyl)-3-Hydroxypropionic Acid and Its Quantification in Human Urine Samples |
title_full_unstemmed | A Simple and Convenient Synthesis of Unlabeled and (13)C-Labeled 3-(3-Hydroxyphenyl)-3-Hydroxypropionic Acid and Its Quantification in Human Urine Samples |
title_short | A Simple and Convenient Synthesis of Unlabeled and (13)C-Labeled 3-(3-Hydroxyphenyl)-3-Hydroxypropionic Acid and Its Quantification in Human Urine Samples |
title_sort | simple and convenient synthesis of unlabeled and (13)c-labeled 3-(3-hydroxyphenyl)-3-hydroxypropionic acid and its quantification in human urine samples |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6316614/ https://www.ncbi.nlm.nih.gov/pubmed/30469313 http://dx.doi.org/10.3390/metabo8040080 |
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