Epoc group: transformable protecting group with gold(iii)-catalyzed fluorene formation |
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| Authors: | Tomoya Yamamoto Tsung-Che Chang Katsunori Tanaka |
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| Affiliation: | Biofunctional Synthetic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako-shi, Saitama 351-0198 Japan.; Department of Chemical Science and Engineering, School of Materials and Chemical Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8552 Japan ; Biofunctional Chemistry Laboratory, Alexander Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlyovskaya Street, 420008 Kazan Russian Federation |
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| Abstract: | This study presents the novel concept of a transformable protecting group, which changes its properties through structural transformation. Based on this concept, we developed a 2-(2-ethynylphenyl)-2-(5-methylfuran-2-yl)-ethoxycarbonyl (Epoc) group. The Epoc group was transformed into an Fmoc-like structure with gold(iii)-catalyzed fluorene formation and was removable under Fmoc-like mild basic conditions post-transformation even though it was originally stable under strongly basic conditions. As an application for organic synthesis, the Epoc group provides the novel orthogonality of gold(iii)-labile protecting groups in solid-phase peptide synthesis. In addition, the high turnover number of fluorene formation in aqueous media is suggestive of the applicability of the Epoc group to biological systems.A protecting group removable with gold(iii)-catalyzed fluorene formation and the subsequent addition of piperidine was developed. |
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