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Design of a stabilized short helical peptide and its application to catalytic enantioselective epoxidation of (E)-chalcone |
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| Authors: | Nanako Yamagata Yosuke Demizu Yukiko SatoMitsunobu Doi Masakazu TanakaKazuo Nagasawa Haruhiro OkudaMasaaki Kurihara |
| Institution: | a Division of Organic Chemistry, National Institute of Health Sciences, 1-18-1, Kamiyoga, Setagaya, Tokyo 158-8501, Japan b Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology, Tokyo 184-8588, Japan c Osaka University of Pharmaceutical Sciences, Osaka 569-1094, Japan d Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan |
| Abstract: | Stabilized short helical heptapeptides containing a combination of an α-aminoisobutyric acid as a helical promoter and l/d-serine derivatives to produce cross-linked units were synthesized. The cyclic peptide R3,7R-2, which had d-serine derivatives at its 3rd and 7th positions, formed a stable right-handed (P) α-helix in solution and the crystalline state. Furthermore, its N-terminal free helical peptide catalyzed the enantioselective epoxidation of (E)-chalcone to afford the epoxide in a high yield and moderate enantioselectivity. |
| Keywords: | Peptide Helix X-ray crystallographic analysis Organocatalyst Enantioselective epoxidation |
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