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Total synthesis of miraziridine A and identification of its major reaction site for cathepsin B |
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| Authors: | Hiroyuki Konno Kanako Kubo Emi Toshiro Kazuto Nosaka |
| Institution: | a Department of Chemistry, Graduate School of Medical Science, Kyoto Prefectural University of Medicine, Kita-ku, Kyoto 603-8334, Japan b Sciences of Functional Foods, Graduate School of Agriculture, Shinshu University, Minamiminowa, Kamiina, Nagano 399-4598, Japan c Department of Biological Science and Technology, Faculty of Engineeing, University of Tokushima, Minamijosanjima, Tokushima 770-8506, Japan |
| Abstract: | The synthesis of miraziridine A, a pentapeptide derivative isolated from marine sponge, and its truncated analogs has been achieved. To construct the backbone of miraziridine A, a side-chain-unprotected vinylogous arginine was condensed with an aziridine-containing fragment prepared by a conventional solid-phase procedure. An analog lacking the vinylogous arginine site showed comparable inhibitory activity with miraziridine A, whereas an analog lacking the aziridine site showed remarkably weak inhibitory activity for cathepsin B. |
| Keywords: | Miraziridine A Cysteine protease inhibitor Cathepsin B Aziridine Vinylogous arginine |
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