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Synthesis and biological activity of (24E)- and (24Z)-26-hydroxydesmosterol

Ratni Saini, Olga Kataeva, Arndt W Schmidt, Yuqin Wang Orcid Logo, Anna Meljon, William Griffiths Orcid Logo, Hans-Joachim Knölker

Bioorganic & Medicinal Chemistry

Swansea University Authors: Yuqin Wang Orcid Logo, William Griffiths Orcid Logo

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DOI (Published version): 10.1016/j.bmc.2013.07.015

Abstract

Using 3b-hydroxychol-5-en-24-oic acid (4) as starting material, the diastereoisomeric allylic alcohols (24E)-26-hydroxydesmosterol (2) and (24Z)-26-hydroxydesmosterol (3) have been synthesised in six steps with 67% and 12% overall yield, respectively. Both of these isomers are found in newborn mouse...

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Published in: Bioorganic & Medicinal Chemistry
ISSN: 0968-0896
Published: 2013
Online Access: Check full text

URI: https://cronfa.swan.ac.uk/Record/cronfa15364
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first_indexed 2013-08-22T01:57:45Z
last_indexed 2018-02-09T04:47:16Z
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spelling 2013-08-02T08:52:06.3998688 v2 15364 2013-08-02 Synthesis and biological activity of (24E)- and (24Z)-26-hydroxydesmosterol c92729b58622f9fdf6a0e7d8f4ce5081 0000-0002-3063-3066 Yuqin Wang Yuqin Wang true false 3316b1d1b524be1831790933eed1c26e 0000-0002-4129-6616 William Griffiths William Griffiths true false 2013-08-02 BMS Using 3b-hydroxychol-5-en-24-oic acid (4) as starting material, the diastereoisomeric allylic alcohols (24E)-26-hydroxydesmosterol (2) and (24Z)-26-hydroxydesmosterol (3) have been synthesised in six steps with 67% and 12% overall yield, respectively. Both of these isomers are found in newborn mouse brain where sterol synthesis is high. Unlike desmosterol (1), neither of these isomers is a ligand to the liver x receptors and thus represents a novel biological deactivation mechanism avoiding cholesterol synthesis. Journal Article Bioorganic & Medicinal Chemistry 0968-0896 31 12 2013 2013-12-31 10.1016/j.bmc.2013.07.015 COLLEGE NANME Biomedical Sciences COLLEGE CODE BMS Swansea University 2013-08-02T08:52:06.3998688 2013-08-02T08:49:58.3505513 Faculty of Medicine, Health and Life Sciences Swansea University Medical School - Medicine Ratni Saini 1 Olga Kataeva 2 Arndt W Schmidt 3 Yuqin Wang 0000-0002-3063-3066 4 Anna Meljon 5 William Griffiths 0000-0002-4129-6616 6 Hans-Joachim Knölker 7
title Synthesis and biological activity of (24E)- and (24Z)-26-hydroxydesmosterol
spellingShingle Synthesis and biological activity of (24E)- and (24Z)-26-hydroxydesmosterol
Yuqin Wang
William Griffiths
title_short Synthesis and biological activity of (24E)- and (24Z)-26-hydroxydesmosterol
title_full Synthesis and biological activity of (24E)- and (24Z)-26-hydroxydesmosterol
title_fullStr Synthesis and biological activity of (24E)- and (24Z)-26-hydroxydesmosterol
title_full_unstemmed Synthesis and biological activity of (24E)- and (24Z)-26-hydroxydesmosterol
title_sort Synthesis and biological activity of (24E)- and (24Z)-26-hydroxydesmosterol
author_id_str_mv c92729b58622f9fdf6a0e7d8f4ce5081
3316b1d1b524be1831790933eed1c26e
author_id_fullname_str_mv c92729b58622f9fdf6a0e7d8f4ce5081_***_Yuqin Wang
3316b1d1b524be1831790933eed1c26e_***_William Griffiths
author Yuqin Wang
William Griffiths
author2 Ratni Saini
Olga Kataeva
Arndt W Schmidt
Yuqin Wang
Anna Meljon
William Griffiths
Hans-Joachim Knölker
format Journal article
container_title Bioorganic & Medicinal Chemistry
publishDate 2013
institution Swansea University
issn 0968-0896
doi_str_mv 10.1016/j.bmc.2013.07.015
college_str Faculty of Medicine, Health and Life Sciences
hierarchytype
hierarchy_top_id facultyofmedicinehealthandlifesciences
hierarchy_top_title Faculty of Medicine, Health and Life Sciences
hierarchy_parent_id facultyofmedicinehealthandlifesciences
hierarchy_parent_title Faculty of Medicine, Health and Life Sciences
department_str Swansea University Medical School - Medicine{{{_:::_}}}Faculty of Medicine, Health and Life Sciences{{{_:::_}}}Swansea University Medical School - Medicine
document_store_str 0
active_str 0
description Using 3b-hydroxychol-5-en-24-oic acid (4) as starting material, the diastereoisomeric allylic alcohols (24E)-26-hydroxydesmosterol (2) and (24Z)-26-hydroxydesmosterol (3) have been synthesised in six steps with 67% and 12% overall yield, respectively. Both of these isomers are found in newborn mouse brain where sterol synthesis is high. Unlike desmosterol (1), neither of these isomers is a ligand to the liver x receptors and thus represents a novel biological deactivation mechanism avoiding cholesterol synthesis.
published_date 2013-12-31T03:17:31Z
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score 11.037603

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