Research

Chemo-enzymatic synthesis of cyclic peptides

M. Kobayashi, N. Onozawa, K. Matsuda, T. Wakimoto, Chemoenzymatic tandem cyclization for the facile synthesis of bicyclic peptides. Commun. Chem. 7, in press (2024)
M. Kobayashi, K. Fujita, K. Matsuda, T. Wakimoto, Streamlined chemoenzymatic synthesis of cyclic peptides by non-ribosomal peptide cyclases. J. Am. Chem. Soc. 145, 3270-3275 (2023)
M. Kobayashi, K. Fujita, K. Matsuda, T. Wakimoto, Chemoenzymatic synthesis of non-ribosomal macrolactam by a penicillin binding protein-type thioesterase. Method Mol. Biol. 2670, 127-144 (2023)
K. Matsuda, K. Fujita, T. Wakimoto, PenA, a penicillin-binding protein-type thioesterase specialized for small peptide cyclization. J. Ind. Microbiol. Biotechnol. 48, kuab023 (2021)
K. Matsuda, R. Zhai, T. Mori, M. Kobayashi, A. Sano, I. Abe, T. Wakimoto, Heterochiral coupling in non-ribosomal peptide macrolactamization. Nature Catalysis. 3, 507-515 (2020)
K. Matsuda, M. Kobayashi, T. Kuranaga, K. Takada, H. Ikeda, S. Matsunaga, T. Wakimoto, SurE is a trans-acting thioesterase cyclizing two distinct non-ribosomal peptides. Org. Biomol. Chem. 17, 1058-1061 (2019)
K. Matsuda, T. Kuranaga, T. Wakimoto, A new cyclase family catalyzing head-to-tail macrolactamization of non-ribosomal peptides. J. Synth. Org. Chem. Jpn. 77, 1106-1115 (2019)
T. Kuranaga, K. Matsuda, A. Sano, M. Kobayashi, A. Ninomiya, K. Takada, S. Matsunaga, T. Wakimoto, Total synthesis of a non-ribosomal peptide surugamide B and identification of a new offloading cyclase family. Angew. Chem. Int. Ed., 57, 9447-9451 (2018)

Biosynthetic study of bioactive natural products

K. Matsuda, H. Maruyama, K. Imachi, H. Ikeda, T. Wakimoto, Actinobacterial chalkophores: the biosynthesis of hazimycins. J. Antibiot. 77, 228-237 (2024)
K. Arima, S. Akiyama, K. Shin-ya, K. Matsuda, T. Wakimoto, Carrier protein mediated formation of the dihydropyridazinone ring in actinopyridazinone biosynthesis. Angew. Chem. Int. Ed. 62, e202305155 (2023)
K. Matsuda, K. Arima, S. Akiyama, Y. Yamada, Y. Abe, H. Suenaga, J. Hashimoto, K. Shin-ya, M. Nishiyama, T. Wakimoto, A natural dihydropyridazinone scaffold generated from a unique substrate for a hydrazine-forming enzyme. J. Am. Chem. Soc. 144, 12954-12960 (2022)
C. S. Phan, K. Matsuda, N. Ballo, K. Fujita, T. Wakimoto, T. Okino, Argicyclamides A–C unveil enzymatic basis for guanidine bis-prenylation. J. Am. Chem. Soc. 143, 10083-10087 (2021)

Uncultured bacteria as sources of bioactive natural products

S. Leopold-Messer, C. Chepkirui, M. F. J. Mabesoone, J. Meyer, L. Paoli, S. Sunagawa, A. R. Uria, T.Wakimoto, J. Piel, Animal-associated marine Acidobacteria with a rich natural-product repertoire. Chem, 9, 3696-3713 (2023)
T. Jomori, K. Matsuda, Y. Egami, I. Abe, A. Takai, T. Wakimoto, Insights into phosphatase-activated chemical defense in a marine sponge holobiont. RSC Chem. Biol. 2, 1600-1607 (2021)
I. F. M. Rumengan, V. I. Y. Roring, J. R. Haedar, M. S. Siby, A. H. Luntungan, B. J. Kolondam, A. Uria, T. Wakimoto, Ascidian-associated photosymbionts from Manado, Indonesia: secondary metabolites, bioactivity simulation, and biosynthetic insight. Symbiosis, 84, 71-82 (2021)
T. Wakimoto, Y. Egami, Y. Nakashima, Y. Wakimoto, T. Mori, T. Awakawa, T. Ito, H. Kenmoku, Y. Asakawa, J. Piel, I. Abe: Calyculin biogenesis from a pyrophosphate protoxin produced by a sponge symbiontNature Chem. Biol. 10, 648-655 (2014) M. C. Wilson, T. Mori, C. Rückert, A. R. Uria, M. J. Helf, K. Takada, C. Gernert, U. Steffens, N. Heycke, S. Schmitt, C. Rinke, E. J. N. Helfrich, A. O. Brachmann, C. Gurgui, T. Wakimoto, M. Kracht, M. Crüsemann, U. Hentschel, I. Abe, S. Matsunaga, J. Kalinowski, H. Takeyama, J. Piel: An environmental bacterial taxon with a large and distinct metabolic repertoireNature 506, 58-62 (2014) 

Isolation and structure elucidation of new natural products

A. Yoshimura, R. Saeki, R. Nakada, S. Tomimoto, T. Jomori, K. Suganuma, T. Wakimoto, Membrane-vesicle-mediated interbacterial communication activates silent secondary metabolite productions. Angew. Chem. Int. Ed. 62, e202307304 (2023)
J. R. Haedar, A. R. Uria, S. Lallo, D. F. Dibwe, T. Wakimoto, New theonellapeptolides from Indonesian marine sponge Theonella swinhoei as anti-Austerity agents. Mar. Drugs 20, 661 (2022)
M. Kimura, T. Wakimoto, Y. Egami, K. C. Tan, Y. Ise, I. Abe: Calyxamides A and B, cytotoxic cyclic peptides from the marine sponge Discodermia calyxJ. Nat. Prod. 75, 290-294 (2012)
T. Wakimoto, T. Asakawa, S. Akahoshi, T. Suzuki, K. Nagai, H. Kawagishi, T. Kan: Proof of the existence of an unstable amino acid, pleurocybellaziridine, in Pleurocybella porrigens (angel’s wing mushroom)Angew. Chem. Int. Ed. 50, 1168-1170 (2011)

Active ingredients in foods and traditional medicines

A. Takeuchi, A. Hirata, A. Teshima, M. Ueki, T. Satoh, K. Matsuda, T. Wakimoto, K. Arakawa, M. Ishikawa, T. Suzuki, Characterization of the surugamide biosynthetic gene cluster of TUA-NKU25, a Streptomyces diastaticus strain isolated from Kusaya, and its effects on salt-dependent growth. Biosci. Biotechnol. Biochem., zbac201 (2022)
T. Wakimoto, H. Kondo, H. Nii, K. Kimura, Y. Egami, Y. Oka, M. Yoshida, E. Kida, Y. Ye, S. Akahoshi, T. Asakawa, K. Matsumura, H. Ishida, H. Nukaya, K. Tsuji, T. Kan, I. Abe: Furan fatty acid as an anti-inflammatory component from green-lipped mussel, Perna canaliculusProc. Natl. Acad. Sci. USA108, 17533-17537 (2011)