Stereoselective synthesis of the hormonally active (25S)-delta7-dafachronic acid, (25S)-Delta4-dafachronic acid, (25S)-dafachronic acid, and (25S)-cholestenoic acid.
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.
Martin
René
R
Department Chemie, Technische Universität Dresden, Bergstrasse 66, 01069 Dresden, Germany.
Däbritz
Frank
F
Entchev
Eugeni V
EV
Kurzchalia
Teymuras V
TV
Knölker
Hans-Joachim
HJ
D000818:Animals; D017173:Caenorhabditis elegans / Q000378:metabolism; D029742:Caenorhabditis elegans Proteins / Q000378:metabolism; D002782:Cholestenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D004875:Ergosterol / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D018160:Receptors, Cytoplasmic and Nuclear / Q000378:metabolism; D013237:Stereoisomerism; D013379:Substrate Specificity
D029742:Caenorhabditis elegans Proteins; D002782:Cholestenes; C410905:DAF-12 protein, C elegans; D018160:Receptors, Cytoplasmic and Nuclear; C514718:cholestenoic acid; C533800:dafachronic acid; C533799:delta4-dafachronic acid; C533798:delta7-dafachronic acid; D004875:Ergosterol