949004-11-9Relevant academic research and scientific papers
Mixed bioengineering-chemical synthesis approach for the efficient preparation of δ7-dafachronic acid
Kinzurik, Matias I.,Hristov, Lachezar V.,Matsuda, Seiichi P. T.,Ball, Zachary T.
supporting information, p. 2188 - 2191 (2014/05/06)
Combining bioengineering with chemical synthesis has enabled an efficient method for producing δ7-dafachronic acid, a steroidal hormone associated with nematode germline longevity. Saccharomyces cerevisiae was engineered to produce 7,24-cholestadienol, a convenient starting material for a four-step synthesis of δ7-dafachronic acid.
A photocleavable masked nuclear-receptor ligand enables temporal control of C.elegans development
Judkins, Joshua C.,Mahanti, Parag,Hoffman, Jacob B.,Yim, Isaiah,Antebi, Adam,Schroeder, Frank C.
, p. 2110 - 2113 (2014/03/21)
The development and lifespan of C.elegans are controlled by the nuclear hormone receptor DAF-12, an important model for the vertebrate vitaminD and liverX receptors. As with its mammalian homologues, DAF-12 function is regulated by bile acid-like steroidal ligands; however, tools for investigating their biosynthesis and function invivo are lacking. A flexible synthesis for DAF-12 ligands and masked ligand derivatives that enable precise temporal control of DAF-12 function was developed. For ligand masking, photocleavable amides of 5-methoxy-N-methyl-2-nitroaniline (MMNA) were introduced. MMNA-masked ligands are bioavailable and after incorporation into the worm, brief UV irradiation can be used to trigger the expression of DAF-12 target genes and initiate development from dauer larvae into adults. The invivo release of DAF-12 ligands and other small-molecule signals by using photocleavable MMNA-masked ligands will enable functional studies with precise spatial and temporal resolution. Copyright
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.,Knoelker, Hans-Joachim
experimental part, p. 909 - 920 (2009/05/30)
We describe the stereoselective transformation of diosgenin (4a) to (25R)-Δ4-dafachronic acid (1a), (25R)-Δ7- dafachronic acid (2a), and (25R)-cholestenoic acid (3a), which represent potential ligands for the hormonal receptor DAF-12
Stereoselective synthesis of (25r)-dafachronic acids and (25R)-cholestenoic acid as potential ligands for the DAF-12 receptor in Caenorhabditis elegans
Martin, René,Schmidt, Arndt W.,Theumer, Gabriele,Kurzchalia, Teymuras V.,Kn?lker, Hans-Joachim
scheme or table, p. 1965 - 1968 (2009/04/11)
Commercially available diosgenin has been used as starting material for a highly efficient synthesis of (25R)-dafachronic acids and (25R)-cholestenoic acid, potential ligands for the receptor DAF-12 in the nematode Caenorhabditis elegans.
An efficient, stereocontrolled synthesis of the 25-(R)-diastereomer of dafchronic acid A from β-ergosterol
Giroux, Simon,Corey
supporting information; experimental part, p. 801 - 802 (2009/04/07)
A direct and stereocontrolled synthesis of the 25-(R)-diastereomer of dafachronic acid A from β-ergosterol has been developed.
