Practical synthesis of blepharismone,a mating inducing pheromone of Blepharisma japonicum |
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| Affiliation: | 1. Department of Material Science, Graduate School of Science, Osaka City University, Osaka 558-8585, Japan;2. Department of Molecular Cellular and Animal Biology, University of Camerino, Via F. Camerini 2, 62032 Camerino (MC), Italy;1. Pharmaceutical Research Center, Guangzhou Medical University, 195# Dongfengxi Road, Guangzhou 510182, China;2. School of Pharmaceutical Sciences, Jinan University, Guangzhou 510632, China;1. Faculty of Science, Yamagata University, Kojirakawa-machi 1-4-12, Yamagata 990-8560, Japan;2. Department of Electric and Electronic Engineering, Faculty of Science and Engineering, Kindai University, Kowakae 3-4-1, Higashi-osaka, Osaka 577-8502, Japan;3. Department of Chemistry, Faculty of Science and Engineering, Kindai University, Kowakae 3-4-1, Higashi-osaka, Osaka 577-8502, Japan;4. Department of Applied Chemistry and Biochemistry, Faculty of Engineering, Kyushu Sangyo University, 2-3-1 Matsukadai, Higashi-ku, Fukuoka 813-8503, Japan;1. Department of Life Sciences, National University of Kaohsiung, Kaohsiung 811, Taiwan;2. Department of Microbiology, Kaohsiung Medical University, Kaohsiung 807, Taiwan;3. Department of Marine Biotechnology and Resources, National Sun Yat-Sen University, Kaohsiung 804, Taiwan;4. Center of Asia-Pacific Marine Researches, National Sun Yat-sen University, Kaohsiung, Taiwan;1. Department of Chemistry, University of Zanjan, P.O. Box 45195-313, Zanjan, Islamic Republic of Iran;2. Department of Chemistry, Faculty of Sciences, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Islamic Republic of Iran;3. Department of Chemie, Ludwig-Maximilians-Universität München Butenandtstr. 5-13, Haus D81377 München, Germany |
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| Abstract: | Both enantiomers of blepharismone, a mating inducing pheromone produced by type II cells of Blepharisma japonicum, were synthesized via the Stille cross-coupling reaction of [4-(tert-butyl-dimethyl-silanyloxy)-2-trimethylstannanyl-phenyl]-carbamic acid tert-butyl ester with an acid chloride derived from (S)- and (R)-malic acid as a key reaction. The mating inducing activity of synthetic (S)-blepharismone was as effective as that of the natural one. The enantiomer (R)-blepharismone showed no mating inducing activity. |
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