Synthesis and biological activity of the (25R)-cholesten-26-oic acids-ligands 
for the hormonal receptor DAF-12 in Caenorhabditis elegans

Martin, Rene; Schmidt, Arndt W; Theumer, Gabriele; Krause, Tilo; Entchev, Eugeni V; Kurzchalia, Teymuras V; Knolker, Hans-Joachim

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Synthesis and biological activity of the (25R)-cholesten-26-oic acids-ligands for the hormonal receptor DAF-12 in Caenorhabditis elegans

Martin, R., Schmidt, A. W., Theumer, G., Krause, T., Entchev, E. V., Kurzchalia, T. V., et al. (2009). Synthesis and biological activity of the (25R)-cholesten-26-oic acids-ligands for the hormonal receptor DAF-12 in Caenorhabditis elegans. Organic & Biomolecular Chemistry, 7(5), 909-920.

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Item Permalink: https://hdl.handle.net/21.11116/0000-0001-0D82-E Version Permalink: https://hdl.handle.net/21.11116/0000-0001-0D83-D

Genre: Journal Article

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Martin, Rene, Author
Schmidt, Arndt W, Author
Theumer, Gabriele, Author
Krause, Tilo, Author
Entchev, Eugeni V¹, Author
Kurzchalia, Teymuras V¹, Author
Knolker, Hans-Joachim, Author

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1Max Planck Institute of Molecular Cell Biology and Genetics, Max Planck Society, ou_2340692

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Abstract: We describe the stereoselective transformation of diosgenin () to (25R)-Delta(4)-dafachronic acid (), (25R)-Delta(7)-dafachronic acid (), and (25R)-cholestenoic acid (), which represent potential ligands for the hormonal receptor DAF-12 in Caenorhabditis elegans. Key-steps of our synthetic approach are a modified Clemmensen reduction of diosgenin () and a double bond shift from the 5,6- to the 7,8-position. In the 25R-series, the Delta(7)-dafachronic acid exhibits the highest hormonal activity.

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Dates: Date issued: 2009

Publication Status: Issued

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Identifiers: eDoc: 463140
Other: 1136

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Title: Organic & Biomolecular Chemistry

Source Genre: Journal

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Pages: - Volume / Issue: 7 (5) Sequence Number: - Start / End Page: 909 - 920 Identifier: -