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2020

発表論文

  • Zhang Z., Qiao T., Watanabe K.,* and Tang Y.* Concise biosynthesis of phenylfuropyridones from fungi. Angew. Chem. Int. Ed., in press.https://onlinelibrary.wiley.com/doi/10.1002/anie.202008321

    • Watanabe D., Murakami H., Ohno H., Tanisawa K., Konishi K., Tsunematsu Y., Sato M., Miyoshi N, Wakabayashi K., Watanabe K., and Miyachi M. Association between dietary intake and the prevalence of tumourigenic bacteria in the gut microbiota of middle-aged Japanese adults. Sci. Rep., in press.

      • Asai, S., Tsunematsu, Y., Masuya, T., Otaka, J. Osada, H., Watanabe, K. Uncovering hidden sesquiterpene biosynthetic pathway through expression boost area-mediated productivity enhancement in basidiomycete. J Antibiot (Tokyo), in press.https://www.nature.com/articles/s41429-020-0355-9

        • Yoshikawa Y., Tsunematsu T., Matsuzaki N., Hirayama Y., Higashiguchi F., Sato M., Iwashita Y., Miyoshi N., Mutoh M., Ishikawa H., Sugimura H., Wakabayashi K., Watanabe K. Characterization of colibactin-producing Escherichia coli isolated from Japanese patients with colorectal cancer. Japanese Journal of Infectious Diseases, in press.

        • Tajima, Y., Toyoda, T., Hirayama, Y., Matsushita, K., Yamada, T., Ogawa, K., Watanabe, K., Takamura-Enya, T., Totsuka, Y., Wakabayashi, K., Miyoshi, N. A novel o-toluidine metabolite in rat urine associated with urinary bladder carcinogenesis. Chemical Research in Toxicology, in press.

        • Sato, M., Kishimoto, S., Noguchi, H., Watanabe, K. Bisindole, Comprehensive Natural Products III: Chemistry and Biology, Wiley, in press.

        • Tsunematsu, Y., Hirayama, Y., Masuya, T., Watanabe, K. Oxidative modification enzymes in polyketide biosynthetic pathways. Comprehensive Natural Products III: Chemistry and Biology, Wiley, in press.

        • Uchikawa M, Kato M, Nagata A, Sanada S, Yoshikawa Y, Tsunematsu Y, Sato M, Suzuki T, Hashidume T, Watanabe K, Yoshikawa Y, Miyoshi N. Elevated levels of proinflammatory volatile metabolites in feces of high fat diet fed KK-Ay mice. Sci. Rep., (2020) in press

        • Sarmales-Murga, C.; Akaoka, F.; Sato, M.; Takanishi, J.; Mino, T.; Miyoshi, N.; Watanabe, K., A new class of dimeric product isolated from the fungus Chaetomium globosum: evaluation of chemical structure and biological activity. J Antibiot (Tokyo), in press. https://doi.org/10.1038/s41429-020-0281-x

        • Masanobu Kawanishi; Chiaki Shimohara; Yoshimitsu Oda; Yuuta Hisatomi; Yuta Tsunematsu; Michio Sato; Yuichiro Hirayama; Noriyuki Miyoshi; Yuji Iwashita; Yuko Yoshikawa; Haruhiko Sugimura; Michihiro Mutoh; Hideki Ishikawa; Keiji Wakabayashi; Takashi Yagi; Kenji Watanabe, Genotyping of a gene cluster for production of colibactin and in vitro genotoxicity analysis of Escherichia coli strains obtained from the Japan Collection of Microorganisms, Genes and Environment, 2020, 42, 12.https://genesenvironment.biomedcentral.com/articles/10.1186/s41021-020-00149-z

書籍

  • 川西優喜、若林敬二、渡辺賢二  腸内細菌叢とがん発生の分子メカニズム 実験医学、vol.38、No.11 (7月号) 2020
  • 渡辺賢二*、遺伝子・細胞からみた応用微生物学、第3章、朝倉書店

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2019

発表論文

  • Kawanishi, M.; Hisatomi, Y.; Oda, Y.; Shimohara, C.; Tsunematsu, Y.; Sato, M.; Hirayama, Y.; Miyoshi, N.; Iwashita, Y.; Yoshikawa, Y.; Sugimura, H.; Mutoh, M.; Ishikawa, H.; Wakabayashi, K.; Yagi, T.; Watanabe, K., In vitro genotoxicity analyses of colibactin-producing E. coli isolated from a Japanese colorectal cancer patient. J. Toxicol. Sci. 2019, 44 (12), 871-876. https://www.jstage.jst.go.jp/article/jts/44/12/44_871/_article

  • Tsunematsu, Y.; Takanishi, J.; Asai, S.; Masuya, T.; Nakazawa, T.; Watanabe, K., Genomic Mushroom Hunting Decrypts Coprinoferrin, A Siderophore Secondary Metabolite Vital to Fungal Cell Development. Org. Lett. 2019, 21 (18), 7582-7586.
    https://pubs.acs.org/doi/10.1021/acs.orglett.9b0286

  • Kishimoto, S.; Tsunematsu, Y.; Matsushita, T.; Hara, K.; Hashimoto, H.; Tang, Y.; Watanabe, K., Functional and Structural Analyses of trans C-Methyltransferase in Fungal Polyketide Biosynthesis. Biochemistry 2019, 58 (38), 3933-3937. 
    https://pubs.acs.org/doi/10.1021/acs.biochem.9b00702

  • Hirayama, Y., Tsunematsu, Y., Yoshikawa, Y., Tamahune, R., Matsuzaki, N., Iwashita, Y., Ohnishi, I., Tanioka, F., Sato, M., Miyoshi, N., Mutoh, M., Ishikawa, H., Sugimura, H., Wakabayashi, K., Watanabe, K. Activity-Based Probe for Screening of High-Colibactin Producers from Clinical Samples. Org. Lett. 2019, 21 (12), 4490-449.
    https://doi.org/10.1021/acs.orglett.9b01345

  • Masuya, T., Tsunematsu, Y., Hirayama, Y., Sato, M., Noguchi, H., Nakazawa, T., Watanabe, K. Biosynthesis of lagopodins in mushroom involves a complex network of oxidation reactions. Org. Biomol. Chem., 17, 234-239, 2019.
    doi: 10.1039/C8OB02814A.

2018

発表論文

  • Tsunematsu, Y., Maeda, N., Yokoyama, M., Chankhamjon, P., Watanabe, K., Scherlach, K., Hertweck, C. Enzymatic amide-tailoring promotes retro-aldol amino acid conversion to form the antifungal agent aspirochlorine. Angew. Chem. Int. Ed., 57, 14051-14054, 2018. doi: 10.1002/anie.201806740

  • Kishimoto, S., Hara, H., Hashimoto, H., Hirayama, Y., Champagne, P. A., Houk, K. N., Tang, Y., Watanabe, K.* Enzymatic one-step ring contraction for quinolone biosynthesis. Nature Communications, 19, 2826, 2018. doi: 10.1038/s41467-018-05221-5.

  • Li, L., Tang, M.C., Tang, S., Gao, S., Soliman, S., Hang, L., Xu, W., Ye, T., Watanabe, K., Tang, Y. Genome mining and assembly-line biosynthesis of the UCS1025A pyrrolizidinone family of fungal alkaloids. J. Am. Chem. Soc., 140, 2067-2071, 2018.

  • Suwama, T., Watanabe, K., Monthakantirat, O., Luecha, P., Noguchi, H., Watanabe, K., Umehara, K. Naphthalene glycosides in the Thai medicinal plant Diospyros mollis. J. Nat. Med., 72, 220-229, 2018.

総説・解説

  • 恒松 雄太, 新規疾患治療法開発のヒントは「微生物の生存戦略」に隠されている?, ファルマシア, 54, 458, 2018.

  • 恒松 雄太, 21世紀における構造未決定天然物 大腸発がんリスク因子コリバクチンの生合成, 有機合成化学協会誌, 76, 490-493, 2018.

  • 大橋雅生, 渡辺賢二*, 天然物生合成におけるS-アデノシルメチオニン依存性酵素により触媒されるペリ環状反応, 現代化学, 563, 51-56, 2018.

著書

  • 渡辺賢二*, 天然物の化学II—第8章 大腸がんバイオマーカーのコリバクチンー; 上村大輔監修; 東京化学同人, 印刷中.

  • Kishimoto, S., Hirayama, Y., Watanabe, K.* Polyketide synthase–nonribosomal peptide synthetase hybrid enzymes of fungi. The Mycota XV: Physiology and Genetics, 367-383, 2018.

2017

発表論文

  • Ohashi, M., Liu, F., Hai, Y., Chen, M., Tang, M.-C., Yang, Z., Sato, M., Watanabe, K.*, Houk, K. N.*, Tang, Y.* SAM-dependent enzyme-catalysed pericyclic reactions in natural product biosynthesis. Nature, 549, 502-506, 2017.

  • Sato, M., Dander, J. E., Sato, C., Hung, Y.-S., Gao, S.-S., Tang, M.-C., Hang, L., Winter, J. M., Garg, N. K.*, Watanabe, K.*, Tang, Y.* Collaborative biosynthesis of maleimide- and succinimide- containing natural products by fungal polyketide megasynthases. J. Am. Chem. Soc., 139, 5317-5320, 2017.

  • Yokoyama, M., Hirayama, Y., Yamamoto, T., Kishimoto, S., Tsunematsu, Y., Watanabe, K.* Integration of chemical, genetic and bioinformatic approaches delineates fungal polyketide–peptide hybrid biosynthesis. Org. Lett., 19, 2001-2005, 2017.

  • Nakazawa, T., Izuno, A., Horii, M., Kodera, R., Nishimura, H., Hirayama, Y., Tsunematsu, Y., Miyazaki, Y., Awano, T., Muraguchi, H., Watanabe, K., Sakamoto, M., Takabe, K., Watanabe, T., Isagi, Y., Honda, Y. Effects of pex1 disruption on wood lignin biodegradation, fruiting development and the utilization of carbon sources in the white-rot Agaricomycete Pleurotus ostreatus and non-wood decaying Coprinopsis cinerea. Fungal Genet. Biol., 109, 7-15, 2017.

  • Zou, Y., Borras, M. G., Tang, M., Hirayama, Y., Li, D., Li, L., Watanabe, K., Houk, K. N., Tang, Y. Enzyme-catalyzed cationic epoxide rearrangements in quinolone alkaloid biosynthesis. Nature Chemical Biology, 13, 325-332, 2017.

  • Torikai, K., Umehara, K., Koga, R., Liu, X., Kitano, T., Watanabe, K., Oishi, T., Noguchi, H., Shimohigashi, Y. Design and synthesis of benzoacridines as estrogenic and anti-estrogenic agents. Bioorg. Med. Chem., 25, 5216-5237, 2017.

  • Tang, M., Zou,Y., Watanabe, K., Walsh, C. T., Tang, Y. Oxidative cyclization in natural product biosynthesis. Chemical Reviews, 117, 5226-5333, 2017.

  • Kishimoto, S., Tsunematsu, Y., Sato, M., Watanabe, K.* Elucidation of biosynthetic pathways of natural products. The Chemicsal Record, 17, 1095-1108, 2017.

総説・解説

  • 渡辺賢二*, 腸内細菌叢由来遺伝毒性物質コリバクチン—腸内細菌叢を起源とする遺伝毒性物質コリバクチンの科学分析手法の確立と日本人コホートにおける発がんとの関連性の解析—; 伊藤 裕 監修; BIO Clinica, 32, 49-52, 2017.

2016

発表論文

  • Li, L., Yu, P., Tang, M. C., Zou, Y., Gao, S.-S., Hung, Y.-S., Zhao, M., Watanabe, K., Houk, K., Tang, Y. Biochemical characterization of an eukaryotic decalin-forming Diels–Alderase. J. Am. Chem. Soc., 138, 15837-15840, 2016.

  • Chankhamjon, P., Tsunematsu, Y., Ishida-Ito, M., Sasa, Y., Meyer, F., Boettger-Schmidt, D., Urbansky, B., Menzel, K. D., Scherlach, K., Watanabe, K., Hertweck, C. Regioselective dichlorination of a non-activated aliphatic carbon and phenol bismethylation by a multifunctional fungal flavoenzyme. Angew. Chem. Int. Ed., 55, 11955-11959, 2016.

  • Yamamoto, T., Tsunematsu, Y., Hara, K., Suzuki, T., Kishimoto, S., Kawagishi, H., Noguchi, H., Hashimoto, H., Tang, Y., Hotta, K., Watanabe, K. Oxidative trans-to-cis isomerization of olefin in polyketide biosynthesis. Angew. Chem. Int. Ed., 55, 6207-6210, 2016.

  • Sato, M., Winter, J. M., Kishimoto, S., Noguchi, H., Tang, Y., Watanabe, K. Combinatorial generation of chemical diversity by redox enzymes in chaetoviridin biosynthesis. Org. Lett., 18, 1446-1449, 2016.

  • Kato, H., Tsunematsu, Y., Yamamoto, T., Namiki, T., Kishimoto, S., Noguchi, H., Watanabe, K. New natural products isolated from Metarhizium robertsii ARSEF 23 by chemical screening and identification of the gene cluster through engineered biosynthesis in Aspergillus nidulans A1145. J. Antibiot., 69, 561-566, 2016.

  • Kishimoto, S., Sato, M., Tsunematsu, Y., Watanabe, K. Evaluation of biosynthetic pathway and engineered biosynthesis of alkaloids. Molecules, 21, 1078-1097, 2016.

2015

原著論文

  • Yamamoto, T., Tsunematsu, Y., Noguchi, H., Hotta, K., Watanabe, K. Elucidation of pyranonigrin biosynthetic pathway reveals a mode of tetramic acid, fused γ-pyrone and exo-methylene formation. Org. Lett., 17, 4992-4995, 2015.

  • Sato, M., Yagishita, F., Mino, T., Uchiyama, N., Patel, A., Chooi, Y.-H., Goda, Y., Xu, W., Noguchi, H., Yamamoto, T., Hotta, K., Houk, K. N., Tang, Y., Watanabe, K. Involvement of lipocalin-like CghA in decalin-forming stereoselective intramolecular [4+2] cycloaddition. ChemBioChem, 16, 2294-2298, 2015.

  • Winter, J., Cascio, D., Dietrich, D., Sato, M., Watanabe, K., Sawaya, M., Vederas, J., Tang, Y. Biochemical and structural basis for controlling chemical modularity in fungal polyketide biosynthesis. J. Am. Chem. Soc., 137, 9885-9893, 2015.

  • Zou, Y., Zhan, Z., Li, D., Tang, M., Watanabe, K., Tang, Y. Tandem prenyltransferases catalyze isoprenoid elongation and complexity generation in biosynthesis of quinolone alkaloids. J. Am. Chem. Soc., 137, 4980-4983, 2015.

  • Wong, F. T., Hotta, K., Chen, X., Fang, M., Watanabe, K., Kim, C. Y. Epoxide hydrolase–lasalocid A structure provides mechanistic insight into polyether natural product biosynthesis. J. Am. Chem. Soc., 137, 86-89, 2015.

  • Sato, M., Yamada, H., Hotta, K., Watanabe, K. Elucidation of shanorellin biosynthetic pathway and functional analysis of associated enzymes. MedChemComm, 6, 425-430, 2015.

総説・解説

  • 渡辺賢二, 抗生物質の化学構造多様性を生み出す酵素の発見とそれら酵素による生物的全合成, The Japanese Journal of Antibiotics, 68, 55-67, 2015.

2014

原著論文

  • Zou, Y., Xu, W., Tsunematsu, Y., Tang, M. C., Watanabe, K., Tang, Y. Methylation-dependent acyl transfer between polyketide synthase and nonribosomal peptide synthetase modules in fungal natural product biosynthesis. Org. Lett., 16, 6390-6393, 2014.

  • Ishikawa, N., Tanaka, H., Koyama, F., Noguchi, H., Wang, C. C., Hotta, K., Watanabe, K. Non-heme dioxygenase catalyzes atypical oxidations to form the 6,6-quinolone core of the viridicatin scaffold. Angew. Chem. Int. Ed., 53, 12880-12884, 2014.

  • Tsunematsu, Y., Fukutomi, M., Saruwatari, T., Noguchi, H., Hotta, K., Tang, Y., Watanabe, K. Elucidation of pseurotin biosynthetic pathway points to trans-acting C-methyltransferase and source of chemical diversity generation. Angew. Chem. Int. Ed., 53, 8475-8479, 2014.

  • Lin, H., Tsunematsu, Y., Dhingra, S., Xu, W., Fukutomi, M., Chooi, Y. H., Cane, D. E., Calvo, A. M., Watanabe, K.,Tang, Y. Generation of complexity in fungal terpene biosynthesis: discovery of a mutifunctional cytochrome P450 in the fumagillin pathway. J. Am. Chem. Soc., 136, 4426-4436, 2014.

  • Saruwatari, T., Yagishita, F., Mino, T., Noguchi, H., Hotta, K., Watanabe, K. Cytochrome P450 as dimerization catalyst in diketopiperazine alkaloid biosynthesis. ChemBioChem., 15, 656-659, 2014.

  • Hotta, K., Keegan, R. M., Ranganathan, S., Fang, M., Bibby, J., Winn, M. D., Sato, M., Lian, M., Watanabe, K., Rigden, D. J., Kim, C. Y. Conversion of a disulfide bond to a thioacetal group during echinomycin biosynthesis. Angew. Chem. Int. Ed., 53, 824-828, 2014.

総説・解説・著書

  • 東口(小山)ふみ, 渡辺賢二, タンパク質どうしの相互作用をとらえる-運ぶだけじゃないアシルキャリアータンパク質の機能-, 化学, 化学同人, 69, 68-69, 2014.

  • 佐藤道大, 渡辺賢二, チオアセタール形成酵素-折り畳まれたエキノマイシン-, 生化学, 日本生化学会, 86, 242-248, 2014.

  • Hotta, K., Watanabe, K. Current understanding and hypotheses on the biosynthesis of microalgal polyether toxins. Toxins and biologically active compounds from microalgae, edited by Gian Paolo Rossini. CRC Press, 1, 281-347, 2014.

  • Watanabe, K. Effective use of heterologous hosts for characterization of biosynthetic enzymes allows production of natural products and promotes new natural product discovery. Chem. Pharm. Bull., 62, 1153-1165, 2014.

2013

原著論文

  • Hiratsuka, T., Koketsu, K., Minami, A., Kaneko, S., Watanabe, C., Watanabe, K., Oguri, H., Oikawa, H. Core scaffold assembly mechanism of quinocarcin and SF-1739: bimodular complex of nonribosomal peptide synthetases for sequential mannich-type reactions. Chemistry & Biology, 20, 1523-1535, 2013.

  • Tsunematsu, Y., Ishikawa, N., Wakana, D., Goda, Y., Noguchi, H., Moriya, H., Hotta, K., Watanabe, K. Spiro-carbon formation by different chemistry involving pathway crosstalk. Nature Chemical Biology, 9, 818-825, 2013.

  • Nakazawa, T., Ishiuchi, K., Sato, M., Tsunematsu, Y., Sugimoto, S., Gotanda, Y., Noguchi, H., Hotta, K., Watanabe, K. Targeted disruption of transcriptional regulators in Chaetomium globosum activates biosynthetic pathways and reveals transcriptional regulator-like behavior of aureonitol. J. Am. Chem. Soc., 135, 13446-13455, 2013.

  • Ishiuchi, K., Nakazawa, T., Yagishita, F., Mino, T., Noguchi, H., Hotta, K., Watanabe, K. Combinatorial generation of complexity by redox enzymes in the chaetoglobosin A biosynthesis. J. Am. Chem. Soc., 135, 7371-7377, 2013.

総説・解説

  • Sato, M., Nakazawa, T., Tsunematsu, Y., Hotta, K., Watanabe, K. Natural product engineering via mechanistic studies of echinomycin biosynthesis. Current Opinion In Chemical Biology, 17, 537-545, 2013.

  • Minami, A., Oguri, H., Watanabe, K., Oikawa, H. Biosynthetic machinery of ionophore polyether lasalocid: enzymatic construction of polyether skeleton. Current Opinion In Chemical Biology, 17, 555-561, 2013.

  • Tsunematsu, Y., Ishiuchi, K., Hotta, K., Watanabe, K. Yeast-based genome mining, production and mechanistic studies of the biosynthesis of fungal polyketide and peptide natural products. Natural Product Reports, 30, 1139-1149, 2013.

2012

原著論文

  • Winter, J. M., Sato, M., Sugimoto, S., Chiou, G., Garg, N. K., Tang, Y., Watanabe, K. Identification and characterization of the chaetoviridin and chaetomugilin gene cluster in Chaetomium globosum reveals dual functions of an iterative highly-reducing polyketide synthase. J. Am. Chem. Soc., 134, 17900-17903, 2012.

  • Minami, A., Shimaya, M., Suzuki, G., Migita, A., Shinde, S. S., Watanabe, K., Tamura, T., Oguri, H., Oikawa, H. Sequential enzymatic epoxidation involved in polyether lasalocid biosynthesis. J. Am. Chem. Soc., 134, 7246-7249, 2012.

  • Tsunematsu, Y., Ichinoseki, S., Nakazawa, T., Ishikawa, N., Noguchi, H., Hotta, K., Watanabe, K. Overexpressing transcriptional regulator in Chaetomium globosum activates a silent biosynthetic pathway: evaluation of shanorellin biosynthesis. J. Antibiot., 65, 377-380, 2012.

  • Ishiuchi, K., Nakazawa, T., Ookuma, T., Sugimoto, T., Sato, M., Tsunematsu, Y., Ishikawa, N., Noguchi, H., Hotta, K., Moriya, H., Watanabe, K. Establishing a new methodology for genome mining and biosynthesis of polyketides and peptides through yeast molecular genetics. ChemBioChem, 13, 846-854, 2012.

  • Nakazawa, T., Ishiuchi, K., Praseuth, A., Noguchi, H., Hotta, K., Moriya, H., Watanabe, K. Overexpressing transcriptional regulator in Aspergillus oryzae activates a silent biosynthetic pathway to produce novel polyketide. ChemBioChem, 13, 855-861, 2012.

  • Hotta, K., Chen, X., Paton, R. S., Minami, A., Li, H., Swaminathan, K., Mathews, I. I., Watanabe, K., Oikawa, H., Houk, K. N., Kim, C. Y. Enzymatic catalysis of anti-Baldwin ring-closure in polyether biosynthesis. Nature, 483, 355-359, 2012.

総説・解説

  • Moriya, H., Makanae, K., Watanabe, K., Chino, A., Shimizu-Yoshida, Y. Robustness analysis of cellular systems using the genetic tug-of-war method. Mol. Biosyst., 8, 2513-2522, 2012.

  • Koketsu, K., Minami, A., Watanabe, K., Oguri, H., Oikawa, H. The pictet-spengler mechanism involved in the biosynthesis of tetrahydroisoquinoline antitumor antibiotics: a novel function for a nonribosomal peptide synthetase. Methods Enzymol., 516, 79-98, 2012.

  • 恒松雄太, 守屋央朗, 渡辺賢二, 出芽酵母発現システムを利用した天然物の生物合成, 化学と生物, 日本農芸化学会, 50, 163-174, 2012.

  • Koketsu, K., Minami, A., Watanabe, K., Oguri, H., Oikawa, H. Pictet-Spenglerase involved in tetrahydroisoquinoline antibiotic biosynthesis. Curr. Opin. Chem. Biol., 16, 142-149, 2012.

  • 中沢威人, 恒松雄太, 石川格靖, 渡辺賢二, 生合成遺伝子クラスターの高度強制発現による合成生物学が拓く有用天然物の創製, 生物工学会誌, 日本生物工学会, 90, 289-292, 2012.

2011

原著論文

  • Torikai, K., Saruwatari, T., Kitano, T., Sano, T., Nakane, A., Noguchi, H., Watanabe, K. Practical synthesis of DOPA derivative for biosynthetic production of potent antitumor natural products, saframycins and ecteinascidin 743. Letters In Organic Chemistry, 8, 686-689, 2011.

  • Hirose, Y., Watanabe, K., Minami, A., Nakamura, T., Oguri, H., Oikawa, H. Involvement of common intermediate L-3-hydroxyknyurenine in the chromophore biosynthesis of quinomycin family antibiotics. J. Antibiot., 64, 117-122, 2011.

  • Minami, A., Migita, A., Inada, D., Hotta, K., Watanabe, K., Oguri, H., Oikawa, H. Enzymatic epoxide-opening cascades catalyzed by a pair of epoxide hydrolases in the ionophore polyether biosynthesis. Org. Lett., 13, 1638-1641, 2011.

総説・解説

  • 渡辺賢二, 大栗博毅, 及川英秋, 生合成マシナリーを用いた抗腫瘍性物質生産の試み, バイオサイエンスとインダストリー, バイオインダストリー協会, 69, 26-30, 2011.

  • Saruwatari, T., Praseuth, A. P., Sato, M., Torikai, K., Noguchi, H., Watanabe, K. A comprehensive overview on genomically directed assembly of aromatic polyketides and macrolide lactones using fungal megasynthases. J. Antibiot., 64, 9-17, 2011.

特許

  • カビ類ポリケチド合成遺伝子の酵母での異種発現
    国際特許, 国際出願番号:PCT/JP2011/004566(出願)
    出願日:平成23年8月11日

2010

  • Koketsu, K., Oguri, H., Watanabe, K., Oikawa, H. Sophisticated enzymatic construction of a pentacyclic scaffold of anticancer agent saframycin. Nature Chemical Biology, 6, 408-410, 2010.

  • Chino, A., Watanabe, K., Moriya, M. Plasmid construction using recombination activity in the fission yeast Schizosaccharomyces pombe. PLoS One, 5, e9652, 2010.

  • Matsuura, Y., Shichijo, Y., Minami, A., Migita, A., Oguri, H., Watanabe, M., Tokiwano, T., Watanabe, K., Oikawa, H. Intriguing substrate tolerance of epoxide hydrolase Lsd19 involved in biosynthesis of the ionophore antibiotic lasalocid A. Org. Lett., 12, 2226-2229, 2010.

特許

  • カビ類ポリケチド合成遺伝子の酵母での異種発現
    特許, 特願2010-181279(出願)
    出願日:平成22年8月13日

2009

  • Goto, Y., Iwasaki, K., Torikai, K., Murakami, H., Suga, H. Ribosomal synthesis of dehydrobutyrine- and methyllanthionine-containing peptides. Chem. Commun., 3419-3421, 2009.

  • Mouri, R., Oishi, T., Torikai, K., Ujihara, S., Matsumori, N., Murata, M., Oshima, Y. Surface plasmon resonance-based detection of ladder-shaped polyethers by inhibition detection method. Bioorg. Med. Chem. Lett., 19, 2824-2828, 2009.

  • Kimura, H., Torikai, K., Ueda, I. Thermal cyclization of nonconjugated aryl-yne-carbodiimide furnishing a dibenzonaphthyridine derivative. Chem. Pharm. Bull., 57, 393-396, 2009.

  • Pickens, L. B., Wang, P., Zhou, H., Kim, W., Watanabe, K., Gomi, S., Tang, Y. Sequence and analysis of the SF2575 gene cluster and characterization of key tailoring enzyme. J. Am. Chem. Soc., 131, 17677-17689, 2009.

  • Watanabe, K., Hotta, K., Nakaya, M., Praseuth, A. P., Wang, C. C. C., Inada, D., Takahashi, K., Fukushi, F., Oguri, H., Oikawa, H. Escherichia coli allows efficient modular incorporation of newly isolated quinomycin biosynthetic enzyme into echinomycin biosynthetic pathway for rational design and synthesis of potent antibiotic unnatural natural product. J. Am. Chem. Soc., 131, 9347-9353, 2009.

  • Watanabe, K., Hotta, K., Praseuth, A. P., Searcey, M., Wang, C. C. C., Oguri, H., Oikawa, H. Rationally Engineered Total Biosynthesis of a Synthetic Analog of a Natural Quinomycin Depsipeptide in Escherichia coli. ChemBioChem, 10, 1965-1968, 2009.

  • Bok, J. W., Chiang, Y. M., Szewczyk, E., Reyes-Domingez, Y., Davidson, A. D., Sanchez, J. F., Lo, H. C., Watanabe, K., Strauss, J., Oakley, B. R., Wang, C. C. C., Keller, N. P. Chromatin-level regulation of biosynthetic gene clusters. Nature Chemical Biology, 5, 462-464, 2009.

  • Migita, A., Watanabe, M., Hirose, Y., Watanabe, K., Tokiwano, T., Kinashi, H., Oikawa, H. Identification of a gene cluster of polyether antibiotic lasalocid from Streptomyces lasaliensis. Biosci. Biotechnol. Biochem., 73, 169-176, 2009.

  • Watanabe, K., Oguri, H., Oikawa, H. Genetic indoctrination of Escherichia coli for innovative drug discovery by way of heterologous expression of the echinomycin biosynthetic pathway. Current Opinion in Chemical Biology, 13, 189-196, 2009.

  • Watanabe, K., Oguri, H, and Oikawa, H. Enzymatic synthesis of molecular skeletons of complex antitumor antibiotics with non-ribosomal peptide synthethases. Journal of Synthetic Organic Chemistry, Japan, 67, 1152-1160, 2009.

  • Watanabe, K., Praseuth, A. P., Praseuth, M. B., Hotta, K. Assembling nonribosomal peptide gene cluster in a heterologous host. Complex enzymes: overview and peptides, edited by David Hopwood. Methods in Enzymology, 458, 379-99, 2009.

  • 鳥飼浩平,菅 裕明.特殊ペプチドの翻訳合成から天然物化学,創薬へ. ファルマシア, 45, 115-119, 2009.

  • 渡辺賢二, 大栗博毅, 及川英秋, 生合成酵素による天然物の全合成―抗腫瘍性物質エキノマイシンの合成を中心に―, 天然物全合成の最新動向; 北泰行監修; シーエムシー出版, 260-275, 2009.

2008

  • Ujihara, S., Oishi, T., Torikai, K., Konoki, K., Matsumori, N., Murata, M., Oshima, Y., Aimoto, S. Interaction of ladder-shaped polyethers with transmembrane α-helix of glycophorin A as evidenced by saturation transfer difference NMR and surface plasmon resonance. Bioorg. Med. Chem. Lett., 18, 6115-6118, 2008.

  • Oishi, T., Hasegawa, F., Torikai, K., Konoki, K., Matsumori, N., Murata, M. Convergent synthesis and biological activity of the WXYZA'B'C' ring system of maitotoxin. Org. Lett., 10, 3599-3602, 2008.

  • Torikai, K., Watanabe, K., Minato, H., Imaizumi, T., Murata, M., Oishi, T. Convergent synthesis of the A-J ring system of yessotoxin. Synlett, 2368-2372, 2008.

  • Torikai, K., Oishi, T., Ujihara, S., Matsumori, N., Konoki, K., Murata, M., Aimoto, S. Design and synthesis of ladder-shaped tetracyclic, heptacyclic, and decacyclic ethers and evaluation of the interaction with transmembrane proteins. J. Am. Chem. Soc., 130, 10217-10226, 2008.

  • Kimura, H., Torikai, K., Miyawaki, K., Ueda, I. Scope of the thermal cyclization of non-conjugated ene-yne-nitrile system: A facile synthesis of cyanofluorenol derivatives. Chem. Lett., 37, 662-663, 2008.

  • Torikai, K., Otsuka, Y., Nishimura, M., Sumida, M., Kawai, T., Sekiguchi, K., Ueda, I. Synthesis and DNA cleaving activity of water-soluble non-conjugated thienyl tetraynes. Bioorg. Med. Chem., 16, 5441-5451, 2008.

  • Shichijo, Y., Migita, A., Oguri, H., Watanabe, M., Tokiwano, T., Watanabe, K., Oikawa, H. Epoxide hydrolase Lsd19 for polyether formation in the biosynthesis of Lasalocid A: direct experimental evidence on polyene-polyepoxide hypothesis in polyether biosynthesis. J. Am. Chem. Soc., 130, 12230-12231, 2008.

  • Praseuth, A. P., Hotta, K., Oguri, H., Oikawa, H., Wang, C. C. C., Watanabe, K. Complete sequence of biosynthetic gene cluster responsible for producing triostin A and evaluation of quinomycin-type antibiotics from Streptomyces triostinicus. Biotechnol. Prog., 24, 1226-1231, 2008.

  • Koketsu, K., Oguri, H., Watanabe, K., Oikawa, H. Enzymatic macrolactonizations in the presence of DNA leading to triostin A analogs. Chemistry & Biology, 15, 818-828, 2008.

  • Chiang, Y., Szewczyk, E., Nayak, T., Sanchez, J. F., Lo, H., Simityan, H., Kuo, E., Praseuth, A., Watanabe, K., Oakley, B. R., Wang, C. C. C. Discovery of the emericellamide gene cluster: an efficient gene targeting system for the genomic mining of natural products in Aspergillus nidulans. Chemistry & Biology, 15, 527-532, 2008.

  • Zhan, J., Watanabe, K., Tang, Y. Synergistic actions of monooxygenase and cyclases in aromatic polyketide biosynthesis. ChemBioChem, 9, 1710-1715, 2008.

  • Zhang, W., Watanabe, K., Cai, X., Jung, M., Tang, Y., Zhan, J. Identifying the minimal enzymes required for anhydrotetracycline biosynthesis. J. Am. Chem. Soc., 130, 6068-6069, 2008.

  • Zhou, H., Zhan, J., Watanabe, K., Xie, X., Tang, Y. A polyketide macrolactone synthase from the filamentous fungus Gibberella zeae. Proc. Natl. Acad. Sci. USA, 105, 6249-6254, 2008.

  • Ma, S. M., Zhan, J., Xie, X., Watanabe, K., Tang, Y., Zhang, W. Redirecting the cyclization steps of fungal polyketide synthase. J. Am. Chem. Soc., 130, 38-39, 2008.

  • Praseuth, A. P., Praseuth, M. B., Oguri, H., Oikawa, H., Watanabe, K., Wang, C. C. C. Improved production of triostin A in engineered Escherichia coli with furnished quinoxaline chromophore by design of experiments in small-scale culture. Biotechnol. Prog., 24, 134-139, 2008.

  • Watanabe. K. Exploring biosythesis of natural products and their inherent aptitude for rational design of desirable compounds through genetic engineering. Biosci. Biotechnol. Biochem., 72, 2491-2506, 2008.

  • 渡辺賢二, 及川英秋, 生合成酵素のみによる有用生物活性天然物の全合成, 化学, 化学同 人, 63, 72-73, 2008.

2007

  • Nakaya, M., Oguri, H., Takahashi, K., Fukushi, E., Watanabe, K., Oikawa, H. Relative and absolute configuration of antitumor agent SW-163D. Biosci. Biotechnol. Biochem., 71, 70371-70378, 2007.

  • Ma, S. M., Zhan, J., Watanabe, K., Xie, X., Zhang, W., Wang, C. C. C., Tang, Y. Enzymatic synthesis of aromatic polyketides using PKS4 from Gibberella fujikuroi. J. Am. Chem. Soc., 129, 10642-10643, 2007.

  • Zhang, W., Wilke, B. I., Zhan, J., Watanabe, K., Boddy C. N., Tang, Y. A new mechanism for benzopyrone formation in aromatic polyketide biosynthesis. J. Am. Chem. Soc., 129, 9304-9305, 2007.

  • Zhang, W., Watanabe, K., Wang, C. C. C., Tang, Y. Investigation of unique early tailoring reactions in the oxytetracycline biosynthetic pathway. J. Biol. Chem., 282, 25717-25725, 2007.

  • Watanabe, K., Praseuth, A. P., Wang, C. C. C. A comprehensive and engaging overview of the type III family of polyketide synthases. Current Opinion in Chemical Biology, 11, 279-286, 2007.

  • Watanabe, K. Oikawa, H. Robust platform for de novo productions of heterologous polyketides and nonribosomal peptides in Escherichia coli. Org. Biomol. Chem., 5, 593-602, 2007.

  • 渡辺賢二, 及川英秋, 抗生物質生合成機構の解明と応用への挑戦, ファルマシア, 日本薬 学会, 43, 679-684, 2007.

2006

  • Torikai, K., Yari, H., Murata, M., Oishi, T. Synthesis of artificial ladder-shaped polyethers containing a 6/7 cis-fused ring system. Heterocycles, 70, 161-167, 2006.

  • Torikai, K., Yari, H., Mori, M., Ujihara, S., Matsumori, N., Murata, M., Oishi, T. Design and synthesis of an artificial ladder-shaped polyether that interacts with glycophorin A. Bioorg. Med. Chem. Lett., 16, 6355-6359, 2006.

  • Watanabe, K., Hotta, K., Praseuth, A. P., Koketsu, K., Migita, A., Boddy, C. N., Wang, C. C. C., Oguri, H., Oikawa, H. Total biosynthesis of antitumor nonribosomal peptides in Escherichia coli. Nature Chemical Biology, 2, 423-428, 2006.

  • Xie, X., Watanabe, K., Wojicicki, W. A., Wang, C. C. C., Tang, Y. Biosynthesis of lavastatin analogs with a broadly specific acyltransferase. Chemistry & Biology, 13, 1161-1169, 2006.

  • Koketsu, K., Oguri, H., Watanabe, K., Oikawa, H. Identification and stereochemical assignment of the β-hydroxytryptophan intermediate in the echinomycin biosynthetic pathway. Org. Lett., 8, 4719-4722, 2006.

  • Zhang, W., Watanabe, K., Wang, C. C. C., Tang, Y. Heterologous biosynthesis of amidated polyketides with novel cyclization regioselectivity from oxytetracycline polyketide synthase. J. Nat. Prod., 69, 1633-1636, 2006.

  • 渡辺賢二, 大栗博毅, 及川英秋, モジュラーポリケタイドおよび非リボソームペプチド合成酵素によって生合成される生物活性物質の大腸菌による生産, 化学と生物, 日本農芸化学会, 44, 609-618, 2006.

  • 渡辺賢二, 大栗博毅, 及川英秋, 大腸菌を利用した抗腫瘍性抗生物質のde novo合成, バ イオテクノロジージャーナル, 羊土社, 6, 720-723, 2006.

  • 渡辺賢二, 大栗博毅, 及川英秋, 抗腫瘍性物質エキノマイシンおよびその誘導体の酵素的 全合成, 化学工業, 化学工業社, 57, 752-756, 2006.

2005

  • Hung, V. S., Hatada, Y., Goda, S., Lu, J., Hidaka, Y., Li, Z., Akita, M., Ohta, Y., Watanabe, K., Matsui, H., Ito, S., Horikoshi, K. α-Glucosidase from a strain of deep-sea Geobacillus: a potential enzyme for the biosynthesis of complex carbohydrates. Appl. Microbiol. Biotechnol., 68, 757-765, 2005.

2004

  • Thompson, T. B., Katayama, K., Watanabe, K., Hutchinson, C. R., Rayment, I. Structural and functional analysis of tetracenomycin F2 cyclase from Streptomyces glaucescens: a type-II polyketide cyclase. J. Biol. Chem., 279, 37956-37963, 2004.

  • Senoura, T., Isono, N., Yoshikawa, M., Asao, A., Hamada, S., Watanabe, K., Ito, H., Matsui, H. Characterization of starch synthase I and II expressed in early developing seeds of kidney bean (Phaseolus vulgaris L.). Biosci. Biotechnol. Biochem., 68, 1949-1960, 2004.

  • Ose, T., Watanabe, K., Yao, M., Honma, M., Oikawa, H., Tanaka, I. Crystal structure of Macrophomate Synthase. Acta Cryst. D, 1187-1197, 2004.

  • Tochihara, T., Sasaki, K., Araki, O., Morimoto, N., Watanabe, K., Hatada, Y., Ito, S., Ito, H., Matsui, H. Site-directed mutagenesis establishes aspartic acid-227 and -342 as essential for enzyme activity in an isomalto-dextranase from Arthrobacter globiformis T6. Biotechnol. Lett., 26, 659-664, 2004.

  • Isono, N., Tochihara, T., Kusnadi, Y., Win, T. T., Watanabe, K., Obae, K., Ito, H., Matsui, H. Cloning and heterologous expression of a β-fructofuranosidase gene from Arthrobacter globiformis IFO 3062, and site-directed mutagenesis of the essential aspartic acid and glutamic acid of the active site. J. Biosci. Bioeng., 97, 244-249, 2004.

  • Isono, N., Senoura, T., Yoshikawa, M., Sakurai, Y., Watanabe, K., Ito, H., Matsui, H. Occurrence of multiple forms for starch synthase II isozyme in developing seeds of kidney bean. J. Appl. Glycosci., 51, 101-107, 2004.

  • Win, T. T., Isono, N., Kusnadi, Y., Watanabe, K., Obae, K., Ito, H., Matsui, H. Enzymatic synthesis of two novel non-reducing oligosaccharides using transfructosylation activity with β-fructofuranosidase from Arthrobacter globiformis. Biotechnol. Lett., 26, 499-503, 2004.

  • Morimoto, N., Yasukawa, Y., Watanabe, K., Unno, T., Ito, H., Matsui, H. Cloning and heterologous Expression of a glucodextranase gene from Arthrobacter globiformis I42, and experimental evidence for the catalytic diad of the recombinant enzyme. J. Biosci. Bioeng., 97, 127-130, 2004.

  • Toyomasu, T., Nakaminami, K., Toshima, H., Mie, T., Watanabe, K., Ito, H., Matsui, H., Mitsuhashi, W., Sassa, T., Oikawa, H. Cloning of a gene cluster responsible for the biosynthesis of diterpene aphidicolin, a specific inhibitor of DNA polymerase α. Biosci. Biotechnol. Biochem., 68, 146-152, 2004.

  • Morimoto, N., Hayase, T., Isono, N., Tochihara, T., Watanabe, K., Ito, H., Matsui, H. Cloning, sequencing and Heterologous expression of the gene encoding glucoamylase from Clostridium thermoamylolyticum and biochemical characterization of the recombinant enzyme. J. Appl. Glycosci., 51, 33-36, 2004.

  • Yamaguchi, K., Morimoto, N., Wang, Y., Watanabe, K., Unno, T., Ito, H., Matsui, H. Cloning and expression of an oligo-1,6-glucosidase gene from Arthrobacter globiformis I42 and biochemical characterization of the recombinant enzyme. J. Appl. Glycosci., 51, 37-40, 2004.

2003

  • Watanabe, K., Rude, M. A., Walsh, C. T., Khosla, C. Engineered biosynthesis of an ansamycin polyketide precursor in Escherichia coli. Proc. Natl. Acad. Sci. USA, 100, 9774-9778, 2003.

  • Watanabe, K., Wang, C. C. C., Boddy, C. N., Cane, D. E., Khosla, C. Understanding substrate specificity of polyketide synthase modules by generating hybrid multimodular synthases. J. Biol. Chem., 278, 42020-42026, 2003.

  • Watanabe, K., Khosla, C., Stroud, R. M., Tsai, S. C. Crystal structure of an acyl-ACP dehydrogenase from the FK520 polyketide biosynthetic pathway: insights into extender unit biosynthesis. J. Mol. Biol., 334, 435-444, 2003.

  • Ose, T., Watanabe, K., Mie, T., Honma, M., Watanabe, H., Yao, M., Oikawa, H., Tanaka, I. Insight into a natural Diels-Alder reaction from the structure of macrophomate synthase. Nature, 422, 185-189, 2003.

  • 渡辺賢二, Combinatorial Biosynthesisへの挑戦: ポリケタイド生合成遺伝子による hybrid multimodular synthasesの基質特異性, 化学と生物, 日本農芸化学会 41, 753-756, 2003.

2000

  • Oikawa, H., Yagi, K., Ohashi, S., Watanabe, K., Mie, T., Ichihara, A., Honma, M., Kobayashi, K. Potent inhibition of macrophomate synthase by reaction intermediate analogs. Biosci. Biotechnol. Biochem., 64, 2368-2379, 2000.

  • Watanabe, K., Mie, T., Ichihara, A., Oikawa, H., Honma, M. Detailed reaction mechanism of macrophomate synthase: extraordinary enzyme catalyzing five-step transformation from 2-pyrones to benzoates. J. Biol. Chem., 275, 38393-38401, 2000.

  • Watanabe, K., Mie, T., Ichihara, A., Oikawa, H., Honma, M. Substrate diversity of macrophomate synthase catalyzing multistep transformation from 2-pyrones to benzoates. Biosci. Biotechnol. Biochem., 64, 530-538, 2000.

  • Watanabe, K., Oikawa, H., Yagi, K., Ohashi, S., Mie, T., Ichihara, A., Honma, M. Macrophomate synthase: characterization, sequence, and expression in Escherichia coli of the novel enzyme catalyzing unusual multistep transformation from 2-pyrones to benzoates. J. Biochem., 127, 467-473, 2000.

  • Watanabe, K., Mie, T., Ichihara, A., Oikawa, H., Honma, M. Reaction mechanism of the macrophomate synthase: experimental evidence on intermediacy of a bicyclic compound. Tetrahedron Lett., 41, 1443-1446, 2000.