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Selective synthesis of dehydroamino acids from threonines |
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| Authors: | Kazuhiko Nakamura Tetsuya Isaka Hiroaki Toshima |
| Institution: | a National Institute of Advanced Industrial Science and Technology (AIST), Central 6-9, Higashi 1-1-1, Tsukuba, Ibaraki 305-8566, Japan b Department of Bioresource Science, College of Agriculture, Ibaraki University, Ami-machi, Inashiki-gun, Ibaraki 300-0393, Japan |
| Abstract: | Dehydropeptides containing dehydroamino acid (ΔAA) are frequently found in natural resources with important biological activity. Herein, we report the selective synthesis of Z- and E-ΔAbu from l- and l-allo-threonine as starting materials through selenation and oxidative elimination. The detailed reaction mechanism of phosphine-assisted selenoether formation is also discussed. |
| Keywords: | Dehydroamino acid Selenyl linker Solid-phase synthesis Reaction mechanism |
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