Synthesis of endogenous sperm-activating and attracting factor isolated from ascidian Ciona intestinalis |
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Authors: | Tohru OishiHiroshi Tsuchikawa Michio Murata Manabu YoshidaMasaaki Morisawa |
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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 |
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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. |
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Keywords: | sperm-activating and attracting factor sterol disulfate structure determination synthesis |
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