Large Nonlinear Effect Observed in the Enantiomeric Excess of Proline in Solution and That in the Solid State†
Yujiro Hayashi Prof. Dr.
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorMasayoshi Matsuzawa
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorJunichiro Yamaguchi
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorSayaka Yonehara
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorYasunobu Matsumoto
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorMitsuru Shoji Dr.
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorDaisuke Hashizume Dr.
RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan
Search for more papers by this authorHiroyuki Koshino Dr.
RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan
Search for more papers by this authorYujiro Hayashi Prof. Dr.
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorMasayoshi Matsuzawa
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorJunichiro Yamaguchi
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorSayaka Yonehara
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorYasunobu Matsumoto
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorMitsuru Shoji Dr.
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorDaisuke Hashizume Dr.
RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan
Search for more papers by this authorHiroyuki Koshino Dr.
RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan
Search for more papers by this authorThis work was partially supported by Toray Science Foundation and a Grant-in-Aid for Scientific Research on Priority Areas 16073219 from MEXT. We thank Professors K. Soai (Tokyo University of Science) and K. Saigo (The University of Tokyo) for helpful discussions.
Graphical Abstract
A clue to the origin of chirality? A solution of proline with high enantiomeric excess (85–99 % ee) was obtained from solid proline of only 10 % ee through novel dissolution and crystallization processes (see scheme). This observation may be an explanation for the origin of chirality on Earth.
Supporting Information
Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2006/z601506_s.pdf or from the author.
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
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