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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...

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Autores principales: Burke, Matthew, Pal, Pratik, Zhang, Peiyi, Zhang, Xuan, Zheng, Guangrong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
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.
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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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