Stereoselective synthesis of the hormonally active (25S)-delta7-dafachronic acid, (25S)-Delta4-dafachronic acid, (25S)-dafachronic acid, and (25S)-cholestenoic acid

Org Biomol Chem. 2008 Dec 7;6(23):4293-5. doi: 10.1039/b815064h. Epub 2008 Oct 17.

Abstract

We report a stereoselective synthesis of the (25S)-cholestenoic-26-acids which are highly efficient ligands for the hormonal receptor DAF-12 in Caenorhabditis elegans.

MeSH terms

  • Animals
  • Caenorhabditis elegans / metabolism
  • Caenorhabditis elegans Proteins / metabolism
  • Cholestenes / chemical synthesis*
  • Cholestenes / chemistry
  • Cholestenes / metabolism
  • Ergosterol / chemical synthesis*
  • Ergosterol / chemistry
  • Ergosterol / metabolism
  • Receptors, Cytoplasmic and Nuclear / metabolism
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Caenorhabditis elegans Proteins
  • Cholestenes
  • DAF-12 protein, C elegans
  • Receptors, Cytoplasmic and Nuclear
  • cholestenoic acid
  • dafachronic acid
  • delta4-dafachronic acid
  • delta7-dafachronic acid
  • Ergosterol