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Synthesis of endogenous sperm-activating and attracting factor isolated from ascidian Ciona intestinalis
Authors:Tohru OishiHiroshi Tsuchikawa  Michio Murata  Manabu YoshidaMasaaki Morisawa
Affiliation:a Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan
b Misaki Marine Biological Station, Graduate School of Science, University of Tokyo, Miura, Kanagawa 238-0225, Japan
Abstract:A chemoattractant candidate named sperm-activating and attracting factor (SAAF) from the eggs of ascidian Ciona intestinalis, was synthesized from chenodeoxycholic acid in 16 steps. The present synthesis led to the unambiguous structure determination of SAAF to be (3R,4R,7R,25S)-3,4,7,26-tetrahydroxycholestane-3,26-disulfate. The synthetic pure specimen was also used to confirm the dual sperm-activating and attracting activity.
Keywords:sperm-activating and attracting factor   sterol disulfate   structure determination   synthesis
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