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          Institute: MPI für molekulare Zellbiologie und Genetik     Collection: Publikationen MPI-CBG 2009 arch     Display Documents



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ID: 463140.0, MPI für molekulare Zellbiologie und Genetik / Publikationen MPI-CBG 2009 arch
Synthesis and biological activity of the (25R)-cholesten-26-oic acids-ligands for the hormonal receptor DAF-12 in Caenorhabditis elegans
Authors:Martin, Rene; Schmidt, Arndt W; Theumer, Gabriele; Krause, Tilo; Entchev, Eugeni V; Kurzchalia, Teymuras V; Knolker, Hans-Joachim
Date of Publication (YYYY-MM-DD):2009
Title of Journal:Organic & Biomolecular Chemistry
Volume:7
Issue / Number:5
Start Page:909
End Page:920
Copyright:not available
Review Status:not specified
Audience:Experts Only
Intended Educational Use:No
Abstract / Description: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.
External Publication Status:published
Document Type:Article
Version Comment:Automatic journal name synchronization
Communicated by:n.n.
Affiliations:MPI für molekulare Zellbiologie und Genetik
Identifiers:LOCALID:1136
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