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4Alpha-bromo-5alpha-cholestan-3beta-ol and nor-5alpha-cholestan-3beta-ol derivatives-stereoselective synthesis and hormonal activity in Caenorhabditis elegans

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Zagoriy,  Vyacheslav
Max Planck Institute of Molecular Cell Biology and Genetics, Max Planck Society;

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Entchev,  Eugeni V
Max Planck Institute of Molecular Cell Biology and Genetics, Max Planck Society;

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Kurzchalia,  Teymuras V
Max Planck Institute of Molecular Cell Biology and Genetics, Max Planck Society;

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Citation

Martin, R., Saini, R., Bauer, I., Gruner, M., Kataeva, O., Zagoriy, V., et al. (2009). 4Alpha-bromo-5alpha-cholestan-3beta-ol and nor-5alpha-cholestan-3beta-ol derivatives-stereoselective synthesis and hormonal activity in Caenorhabditis elegans. Organic & Biomolecular Chemistry, 7(11), 2303-2309.


Cite as: https://hdl.handle.net/21.11116/0000-0001-0CAE-F
Abstract
We describe the stereoselective synthesis of 4alpha-bromo-5alpha-cholestan-3beta-ol, 21-nor-5alpha-cholestan-3beta-ol, 27-nor-5alpha-cholestan-3beta-ol and 21,27-bisnor-5alpha-cholestan-3beta-ol. In order to clarify the in vivo metabolism of cholesterol, these compounds have been used for feeding experiments in Caenorhabditis elegans. Our preliminary results provide important insights into the metabolism of cholesterol in worms.