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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.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Saini R,Kataeva O,Schmidt AW,Wang Y,Meljon A,Griffiths WJ,Knölker HJ

doi

10.1016/j.bmc.2013.07.015

subject

Has Abstract

pub_date

2013-09-15 00:00:00

pages

5794-8

issue

18

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(13)00626-3

journal_volume

21

pub_type

杂志文章

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