Self-Replication and Amplification of Enantiomeric Excess of Chiral Multifunctionalized Large Molecules by Asymmetric Autocatalysis†
Prof. Dr. Tsuneomi Kawasaki
Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/soai/index.html
Research Center for Chirality, Research Institute for Science and Technology (RIST), Tokyo University of Science (Japan)
Present address: Department of Materials Science and Engineering, University of Fukui, Bunkyo, Fukui, 910-8507 (Japan)
Search for more papers by this authorMai Nakaoda
Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/soai/index.html
Search for more papers by this authorYutaro Takahashi
Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/soai/index.html
Search for more papers by this authorYusuke Kanto
Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/soai/index.html
Search for more papers by this authorNanako Kuruhara
Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/soai/index.html
Search for more papers by this authorKenji Hosoi
Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/soai/index.html
Search for more papers by this authorProf. Dr. Itaru Sato
Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/soai/index.html
Present address: Graduate School of Science and Engineering, Ibaraki University, Bunkyo, Ibaraki, 310-8512 (Japan)
Search for more papers by this authorArimasa Matsumoto
Search for more papers by this authorCorresponding Author
Prof. Dr. Kenso Soai
Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/soai/index.html
Research Center for Chirality, Research Institute for Science and Technology (RIST), Tokyo University of Science (Japan)
Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/soai/index.htmlSearch for more papers by this authorProf. Dr. Tsuneomi Kawasaki
Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/soai/index.html
Research Center for Chirality, Research Institute for Science and Technology (RIST), Tokyo University of Science (Japan)
Present address: Department of Materials Science and Engineering, University of Fukui, Bunkyo, Fukui, 910-8507 (Japan)
Search for more papers by this authorMai Nakaoda
Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/soai/index.html
Search for more papers by this authorYutaro Takahashi
Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/soai/index.html
Search for more papers by this authorYusuke Kanto
Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/soai/index.html
Search for more papers by this authorNanako Kuruhara
Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/soai/index.html
Search for more papers by this authorKenji Hosoi
Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/soai/index.html
Search for more papers by this authorProf. Dr. Itaru Sato
Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/soai/index.html
Present address: Graduate School of Science and Engineering, Ibaraki University, Bunkyo, Ibaraki, 310-8512 (Japan)
Search for more papers by this authorArimasa Matsumoto
Search for more papers by this authorCorresponding Author
Prof. Dr. Kenso Soai
Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/soai/index.html
Research Center for Chirality, Research Institute for Science and Technology (RIST), Tokyo University of Science (Japan)
Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/soai/index.htmlSearch for more papers by this authorThis work was supported by a Grant-in-Aid for Scientific Research from Japan Society for the Promotion of Science (JSPS) and MEXT-Supported Program for the Strategic Research Foundation at Private Universities, 2012–2016.
Abstract
Self-replication of large chiral molecular architectures is one of the great challenges and interests in synthetic, systems, and prebiotic chemistry. Described herein is a new chemical system in which large chiral multifunctionalized molecules possess asymmetric autocatalytic self-replicating and self-improving abilities, that is, improvement of their enantioenrichment in addition to the diastereomeric ratio. The large chiral multifunctionalized molecules catalyze the production of themselves with the same structure, including the chirality of newly formed asymmetric carbon atoms, in the reaction of the corresponding achiral aldehydes and reagent. The chirality of the large multifunctionalized molecules controlled the enantioselectivity of the reaction in a highly selective manner to construct multiple asymmetric stereogenic centers in a single reaction.
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