A Simple and Convenient Synthesis of Unlabeled and <sup>13</sup>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...
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| Format: | Article |
| Language: | English |
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MDPI AG
2018-11-01
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| Series: | Metabolites |
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| Online Access: | https://www.mdpi.com/2218-1989/8/4/80 |
| _version_ | 1818821326668824576 |
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| author | Yeganeh Khaniani Matthias Lipfert Dipanjan Bhattacharyya Rolando Perez Pineiro Jiamin Zheng David S. Wishart |
| author_facet | Yeganeh Khaniani Matthias Lipfert Dipanjan Bhattacharyya Rolando Perez Pineiro Jiamin Zheng David S. Wishart |
| author_sort | Yeganeh Khaniani |
| collection | DOAJ |
| 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 <sup>13</sup>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. |
| first_indexed | 2024-12-18T23:06:25Z |
| format | Article |
| id | doaj.art-bd6c001c45ad4077afbc168264617b9a |
| institution | Directory Open Access Journal |
| issn | 2218-1989 |
| language | English |
| last_indexed | 2024-12-18T23:06:25Z |
| publishDate | 2018-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Metabolites |
| spelling | doaj.art-bd6c001c45ad4077afbc168264617b9a2022-12-21T20:48:25ZengMDPI AGMetabolites2218-19892018-11-01848010.3390/metabo8040080metabo8040080A Simple and Convenient Synthesis of Unlabeled and <sup>13</sup>C-Labeled 3-(3-Hydroxyphenyl)-3-Hydroxypropionic Acid and Its Quantification in Human Urine SamplesYeganeh Khaniani0Matthias Lipfert1Dipanjan Bhattacharyya2Rolando Perez Pineiro3Jiamin Zheng4David S. Wishart5Departments of Biological Sciences, University of Alberta, Edmonton, AB T6G 2E8, CanadaDepartments of Biological Sciences, University of Alberta, Edmonton, AB T6G 2E8, CanadaDepartments of Biological Sciences, University of Alberta, Edmonton, AB T6G 2E8, CanadaDepartments of Biological Sciences, University of Alberta, Edmonton, AB T6G 2E8, CanadaDepartments of Biological Sciences, University of Alberta, Edmonton, AB T6G 2E8, CanadaDepartments of Biological Sciences, University of Alberta, Edmonton, AB T6G 2E8, CanadaAn 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 <sup>13</sup>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.https://www.mdpi.com/2218-1989/8/4/80HPHPAbiomarkerisotopic labelingsonicationReformatsky reaction |
| spellingShingle | Yeganeh Khaniani Matthias Lipfert Dipanjan Bhattacharyya Rolando Perez Pineiro Jiamin Zheng David S. Wishart A Simple and Convenient Synthesis of Unlabeled and <sup>13</sup>C-Labeled 3-(3-Hydroxyphenyl)-3-Hydroxypropionic Acid and Its Quantification in Human Urine Samples Metabolites HPHPA biomarker isotopic labeling sonication Reformatsky reaction |
| title | A Simple and Convenient Synthesis of Unlabeled and <sup>13</sup>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 <sup>13</sup>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 <sup>13</sup>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 <sup>13</sup>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 <sup>13</sup>C-Labeled 3-(3-Hydroxyphenyl)-3-Hydroxypropionic Acid and Its Quantification in Human Urine Samples |
| title_sort | simple and convenient synthesis of unlabeled and sup 13 sup c labeled 3 3 hydroxyphenyl 3 hydroxypropionic acid and its quantification in human urine samples |
| topic | HPHPA biomarker isotopic labeling sonication Reformatsky reaction |
| url | https://www.mdpi.com/2218-1989/8/4/80 |
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