Syntheses and biological evaluation of B-ring-modified analogues of dafachronic acid A.
Synthesis and testing of dafachronic acid A ( 1) and its derivatives 2 and 3 have revealed that 1, and not a further oxidation product, is the natural ligand for the DAF-12 receptor of Caenorhabditis elegans.
Giroux
Simon
S
Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
Bethke
Axel
A
Fielenbach
Nicole
N
Antebi
Adam
A
Corey
E J
EJ
D000818:Animals; D017173:Caenorhabditis elegans / Q000235:genetics; D029742:Caenorhabditis elegans Proteins / Q000737:chemistry / Q000187:drug effects* / Q000235:genetics; D004875:Ergosterol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D008024:Ligands; D008968:Molecular Conformation; D018160:Receptors, Cytoplasmic and Nuclear / Q000737:chemistry / Q000187:drug effects* / Q000235:genetics; D013237:Stereoisomerism; D014158:Transcription, Genetic / Q000187:drug effects / Q000235:genetics
D029742:Caenorhabditis elegans Proteins; C410905:DAF-12 protein, C elegans; D008024:Ligands; D018160:Receptors, Cytoplasmic and Nuclear; C528461:dafachronic acid A; D004875:Ergosterol