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Concise Synthesis of (S)-δ-CEHC, a Metabolite of Vitamin E
[Image: see text] Carboxyethyl hydroxychromans (CEHCs) are natural metabolites of vitamin E (VE). Their urinary levels can serve as useful biomarkers for the nutritional assessment of VE. Moreover, specific biological activities of CEHCs deserve further investigation. Here, we report a concise metho...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2021
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7893788/ https://www.ncbi.nlm.nih.gov/pubmed/33623846 http://dx.doi.org/10.1021/acsomega.0c05658 |
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author | Burke, Matthew Pal, Pratik Zhang, Peiyi Zhang, Xuan Zheng, Guangrong |
author_facet | Burke, Matthew Pal, Pratik Zhang, Peiyi Zhang, Xuan Zheng, Guangrong |
author_sort | Burke, Matthew |
collection | PubMed |
description | [Image: see text] Carboxyethyl hydroxychromans (CEHCs) are natural metabolites of vitamin E (VE). Their urinary levels can serve as useful biomarkers for the nutritional assessment of VE. Moreover, specific biological activities of CEHCs deserve further investigation. Here, we report a concise method to build up a chiral 6-hydroxychroman scaffold of VE and CEHCs. The first total synthesis of (S)-δ-CEHC was accomplished in 40% overall yield and 97% ee using a chiral synthon derived from naturally occurring (−)-linalool. |
format | Online Article Text |
id | pubmed-7893788 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-78937882021-02-22 Concise Synthesis of (S)-δ-CEHC, a Metabolite of Vitamin E Burke, Matthew Pal, Pratik Zhang, Peiyi Zhang, Xuan Zheng, Guangrong ACS Omega [Image: see text] Carboxyethyl hydroxychromans (CEHCs) are natural metabolites of vitamin E (VE). Their urinary levels can serve as useful biomarkers for the nutritional assessment of VE. Moreover, specific biological activities of CEHCs deserve further investigation. Here, we report a concise method to build up a chiral 6-hydroxychroman scaffold of VE and CEHCs. The first total synthesis of (S)-δ-CEHC was accomplished in 40% overall yield and 97% ee using a chiral synthon derived from naturally occurring (−)-linalool. American Chemical Society 2021-02-02 /pmc/articles/PMC7893788/ /pubmed/33623846 http://dx.doi.org/10.1021/acsomega.0c05658 Text en © 2021 The Authors. Published by American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes. |
spellingShingle | Burke, Matthew Pal, Pratik Zhang, Peiyi Zhang, Xuan Zheng, Guangrong Concise Synthesis of (S)-δ-CEHC, a Metabolite of Vitamin E |
title | Concise Synthesis of (S)-δ-CEHC,
a Metabolite of Vitamin E |
title_full | Concise Synthesis of (S)-δ-CEHC,
a Metabolite of Vitamin E |
title_fullStr | Concise Synthesis of (S)-δ-CEHC,
a Metabolite of Vitamin E |
title_full_unstemmed | Concise Synthesis of (S)-δ-CEHC,
a Metabolite of Vitamin E |
title_short | Concise Synthesis of (S)-δ-CEHC,
a Metabolite of Vitamin E |
title_sort | concise synthesis of (s)-δ-cehc,
a metabolite of vitamin e |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7893788/ https://www.ncbi.nlm.nih.gov/pubmed/33623846 http://dx.doi.org/10.1021/acsomega.0c05658 |
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