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

Ratni Saini; Olga Kataeva; Arndt W Schmidt; Yuqin Wang; Anna Meljon; William J Griffiths; Hans-Joachim Knölker

doi:10.1016/j.bmc.2013.07.015

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

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

School of Biological Sciences

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

Abstract

Using 3β-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.

Original language	English
Pages (from-to)	5794-8
Number of pages	5
Journal	Bioorganic & Medicinal Chemistry
Volume	21
Issue number	18
DOIs	https://doi.org/10.1016/j.bmc.2013.07.015
Publication status	Published - 15 Sept 2013

Bibliographical note

Keywords

Animals
Brain/metabolism
Crystallography, X-Ray
Desmosterol/analogs & derivatives
Isomerism
Liver X Receptors
Mice
Molecular Conformation
Orphan Nuclear Receptors/chemistry

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10.1016/j.bmc.2013.07.015

Cite this

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title = "Synthesis and biological activity of (24E)- and (24Z)-26-hydroxydesmosterol",

abstract = "Using 3β-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. ",

keywords = "Animals, Brain/metabolism, Crystallography, X-Ray, Desmosterol/analogs & derivatives, Isomerism, Liver X Receptors, Mice, Molecular Conformation, Orphan Nuclear Receptors/chemistry",

author = "Ratni Saini and Olga Kataeva and Schmidt, {Arndt W} and Yuqin Wang and Anna Meljon and Griffiths, {William J} and Hans-Joachim Kn{\"o}lker",

year = "2013",

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doi = "10.1016/j.bmc.2013.07.015",

language = "English",

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journal = "Bioorganic & Medicinal Chemistry",

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T1 - Synthesis and biological activity of (24E)- and (24Z)-26-hydroxydesmosterol

AU - Saini, Ratni

AU - Kataeva, Olga

AU - Schmidt, Arndt W

AU - Wang, Yuqin

AU - Meljon, Anna

AU - Griffiths, William J

AU - Knölker, Hans-Joachim

PY - 2013/9/15

Y1 - 2013/9/15

N2 - Using 3β-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.

AB - Using 3β-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.

KW - Animals

KW - Brain/metabolism

KW - Crystallography, X-Ray

KW - Desmosterol/analogs & derivatives

KW - Isomerism

KW - Liver X Receptors

KW - Mice

KW - Molecular Conformation

KW - Orphan Nuclear Receptors/chemistry

U2 - 10.1016/j.bmc.2013.07.015

DO - 10.1016/j.bmc.2013.07.015

M3 - Article

C2 - 23910990

SN - 0968-0896

VL - 21

SP - 5794

EP - 5798

JO - Bioorganic & Medicinal Chemistry

JF - Bioorganic & Medicinal Chemistry

IS - 18

ER -

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

Abstract

Bibliographical note

Keywords

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