English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT
Add to Basket
  Local TagsRelease HistoryDetailsSummary

Released
Journal Article

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

MPS-Authors
/persons/resource/persons219137

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

/persons/resource/persons219360

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

External Resource
No external resources are shared
Fulltext (restricted access)
There are currently no full texts shared for your IP range.
Fulltext (public)
There are no public fulltexts stored in PuRe
Supplementary Material (public)
There is no public supplementary material available
Citation

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.


Cite as: https://hdl.handle.net/21.11116/0000-0001-0D82-E
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.