Laboratory of Bioorganic Chemistry, Faculty of Engineering, Department of Biotechnology, Toyama Prefectural University

Laboratory of Bioorganic Chemistry, Toyama Prefectural University




  • Watanabe, Y.; Sakata, K.; Urabe, D.; Hagiwara, K.; Inoue, M.
    "Formal Total Synthesis of Batrachotoxin Enabled by Radical and Weix Coupling Reactions"
    J. Org. Chem. 2023, 88, 17479-17484. DOI:10.1021/acs.joc.3c02290
  • Yamaguchi, A.; Kishimoto, T.; Urabe, D.
    "Initial Stage of Syringyl Lignin Formation from Sinapyl Alcohol"
    J. Agric. Food Chem. 2023, 71, 14666-14677. DOI:10.1021/acs.jafc.3c03402
  • Fukaya, K.; Sato, T.; Chida, N.; Urabe, D.
    "Computational Study Focusing on a Comprehensive Conformational Analysis of Transition States for Aza-Spiro Ring Formations with N-Alkoxyamides"
    J. Org. Chem. 2023, 88, 13655-13665. DOI:10.1021/acs.joc.3c01343
  • Liu, C.; Zhang, Z.; Fukaya, K.; Oku, N.; Harunari, E.; Urabe, D.; Igarashi, Y.
    "Isolation and structure determination of allopteridic acids A-C and allokutzmicin from an unexplored actinomycete of the genus Allokutzneria"
    J. Antibiot. 2023, 76, 305-315. DOI:10.1038/s41429-023-00611-4
  • Triningsih, D. W.; Harunari, E.; Fukaya, K.; Oku, N.; Urabe, D.; Igarashi, Y.
    "Species-specific secondary metabolism by actinomycetes of the genus Phytohabitans and discovery of new pyranonaphthoquinones and isatin derivatives"
    J. Antibiot. 2023, 76, 249-259. DOI:10.1038/s41429-023-00605-2
  • Soda, Y.; Sugiyama, Y.; Sato, S.; Shibuya, K.; Saegusa, J.; Matagawa, T.; Kawano, S.; Yoritate, M.; Fukaya, K.; Urabe, D.; Oishi, T.; Mori, K.; Simizu, S.; Chida, N.; Sato, T.
    "Total Synthesis and Anti-inflammatory Activity of Stemoamide-Type Alkaloids Including Totally Substituted Butenolides and Pyrroles,"
    Synthesis, 2023, 55, 617-636. DOI:10.1055/a-1941-8680


  • Lu, S.; Zhou, T.; Fukaya, K.; Harunari, E.; Oku, N.; Urabe, D.; Igarashi, Y.
    "Krasilnikolides A and B and Detalosylkrasilnikolide A, Cytotoxic 20-Membered Macrolides from the Genus Krasilnikovia: Assignment of Anomeric Configuration by J-Based Configuration Analysis,"
    J. Nat. Prod., 2022, 85, 2796-2803. DOI:10.1021/acs.jnatprod.2c00781
  • Hada, K.; Araki, Y.; Nokura, Y.; Urabe, D.; Nishikawa, T.
    "Collective Synthesis of Aplysiatoxin/Oscillatoxin Analogues by a Bioinspired Strategy,"
    J. Org. Chem., 2022, 87, 15618-15633. DOI:10.1021/acs.joc.2c02204
  • Kishimoto, T.; Hiyama, A.; Yamashita, A.; Takano, T.; Tobimatsu, Y.; Urabe, D.
    "Existence of Syringyl α-Carbonyl-Type Tetrahydrofuran β–β Structure in Hardwood Lignins"
    ACS Sustainable Chem. Eng., 2022, 10, 12394-12401. DOI:10.1021/acssuschemeng.2c03861
  • Triningsih, D. W.; Zhou, T.; Fukaya, K.; Harunari, E.; Oku, N.; Urabe, D.; Igarashi, Y.
    "Cyclic enaminones and a 4-quinazolinone from an unidentified actinomycete of the family Micromonosporaceae"
    J. Antibiot., 2022, 75, 610-618. DOI:10.1038/s41429-022-00558-y
  • Harunari, E.; Mae, S.; Fukaya, K.; Tashiro, E.; Urabe, D.; Igarashi, Y.
    "Bisprenyl naphthoquinone and chlorinated calcimycin congener bearing thiazole ring from an actinomycete of the genus Phytohabitans"
    J. Antibiot., 2022, 75, 542-551. DOI:10.1038/s41429-022-00559-x
  • Liu, C.; Zhang, Z.; Fukaya, K.; Urabe, D.; Harunari, E.; Oku, N.; Igarashi, Y.
    "Catellatolactams A-C, Plant Growth-Promoting Ansamacrolactams from a Rare Actinomycete of the Genus Catellatospora"
    J. Nat. Prod., 2022, 85, 1993-1999. DOI:10.1021/acs.jnatprod.2c00331
  • Koizumi, J.; Kaoru, T.; Fukaya, K.; Urabe, D.
    "Stereocontrolled Synthesis of C20S-C26 and C20R-C26 Fragments of Amphidinolide L"
    J. Org. Chem., 2022, 87, 11185-11195. DOI:10.1021/acs.joc.2c01497
  • Karim, Md. R. U.; Fukaya, K.; In, Y.; Sharma, A. R.; Harunari, E.; Oku, N.; Urabe, D.; Trianto, A.; Igarashi, Y.
    "Marinoquinolones and Marinobactoic Acid: Antimicrobial and Cytotoxic ortho-Dialkylbenzene-Class Metabolites Produced by a Marine Obligate Gammaproteobacterium of the Genus Marinobacterium"
    J. Nat. Prod., 2022, 85, 1763-1770. DOI:10.1021/acs.jnatprod.2c00281
  • Matsuyuki, Y.; Fukaya, K.; Urabe, D.
    "RCM approach to the CDE-tricyclic structure of nakiterpiosin"
    Biosci. Biotechnol. Biochem., 2022, 86, 832-836. DOI:10.1093/bbb/zbac061
  • Zhang, Z.; In, Y.; Fukaya, K.; Yang, T.; Harunari, E.; Urabe, D.; Imada, C.; Oku, N.; Igarashi, Y.
    "Kumemicinones A-G, Cytotoxic Angucyclinones from a Deep Sea-Derived Actinomycete of the Genus Actinomadura"
    J. Nat. Prod., 2022, 85, 1098-1108. DOI:10.1021/acs.jnatprod.1c01205
  • Qu, C.; Ogita, S.; Kawamoto, H.; Kishimoto, T.
    "HSQC-NMR analysis of bamboo (Phyllostachys nigra)-cultured cell lignin produced under different phytohormone conditions"
    Holzforschung, 2022, 76, 567-577. DOI:10.1515/hf-2021-0229
  • Kishimoto, T.; Hiyama, A.; Toda, H.; Urabe, D.
    "Effect of pH on the Dehydrogenative Polymerization of Monolignols by Laccases from Trametes versicolor and Rhus vernicifera"
    ACS Omega, 2022, 7, 9846-9852. DOI:10.1021/acsomega.2c00144
  • Iiyama, S.; Fukaya, K.; Yamaguchi, Y.; Watanabe, A.; Yamamoto, H.; Mochizuki, S.; Saio, R.; Noguchi, T.; Oishi, T.; Sato, T.; Chida, N.
    "Total Synthesis of Paclitaxel,"
    Org. Lett., 2022, 24, 202-206. DOI:10.1021/acs.orglett.1c03851


  • Oishi, T.; Fukaya, K.; Sato, T.; Chida N.
    "Crystal structure of (+)-(1S,5S,6S,7S,10S,11S,16S)-16-hydroxy-7-(methoxymethoxy)-11,15,18,18-tetramethyl-3,13-dioxo-2,4-dioxatetracyclo[,5.06,11]octadec-14-en-10-yl benzoate,"
    Acta Cryst., 2021, E77, 1234-1238. DOI:10.1107/S2056989021011518
  • Zhang, Z.; Zhou, T.; Yang, T.; Fukaya, K.; Harunari, E.; Saito, S.; Yamada, K.; Imada, C.; Urabe, D.; Igarashi Y.
    "Nomimicins B-D, new tetronate-class polyketides from a marine-derived actinomycete of the genus Actinomadura,"
    Beilstein J. Org. Chem, 2021, 17, 2194-2202. DOI:10.3762/bjoc.17.141
  • Minamikawa, R.; Fukaya, K.; Kobayashi, A.; Komiya, Y.; Yamamoto, S.; Urabe, D.; Chida, N.; Sato, T.
    "Development of Chiral N-Alkoxyamide Strategy and Application to Asymmetric Total Synthesis of Fasicularin,"
    Synthesis, 2021, 53, 4621-4635. DOI:10.1055/a-1561-7815
  • Igarashi, Y.; Matsuyuki, Y; Yamada, M.; Fujihara, N.; Harunari, E.; Oku, N.; Karim, M. R. U.; Yang, T.; Yamada, K.; Imada, C.; Fukaya, K.; Urabe, D.
    "Structure Determination, Biosynthetic Origin, and Total Synthesis of Akazaoxime, an Enteromycin-Class Metabolite from a Marine-Derived Actinomycete of the Genus Micromonospora,"
    J. Org. Chem., 2021, 86, 6528-6537. DOI:10.1021/acs.joc.1c00358
  • Zhang, Z.; Sibero, M. T., Kai, A.; Fukaya, K.; Urabe, D.; Igarashi, Y.
    "TMKS8A, an antibacterial and cytotoxic chlorinated α-lapachone, from a sea slug-derived actinomycete of the genus Streptomyces,"
    J. Antibiot., 2021, 74, 464-469. DOI:10.1038/s41429-021-00415-4
  • Yamaga, M.; Tani, H.; Nishikawa, M.; Fukaya, K.; Ikushiro, S.; Murota, K.
    "Pharmacokinetics and metabolism of cinnamic acid derivatives and flavonoids after oral administration of Brazilian green propolis in humans,"
    Food Funct., 2021, 12, 2520-2530. DOI:10.1039/D0FO02541K
  • Zhou, T.; Katsuragawa, M.; Xing, T.; Fukaya, K.; Okuda, T.; Tokiwa, T.; Tashiro, E.; Imoto, M.; Oku, N.; Urabe, D.; Igarashi, Y.
    "Cyclopeptides from the Mushroom Pathogen Fungus Cladobotryum varium,"
    J. Nat. Prod., 2021, 84, 327-338. DOI:10.1021/acs.jnatprod.0c00980
  • Urabe, D.; Fukaya, K.
    "Systematic Search for Transition States in Complex Molecules: Computational Analyses of the Regio- and Stereoselective Interflavan Bond Formation in Flavan-3-Ols,"
    Heterocycles, 2021, 102. DOI:10.3987/REV-20-943


  • Qu C.; Ogita, S.; Kishimoto, T.
    "Characterization of immature bamboo (Phyllostachys nigra) component changes with its growth via heteronuclear single-quantum coherence nuclear magnetic resonance spectroscopy,"
    J. Agric. Food Chem., 2020, 68, 9896-9905. DOI:10.1021/acs.jafc.0c02258
  • Karim, Md. R. U.; Harunari, E.; Sharma, A. R.; Oku, N.; Akasaka, K.; Urabe, D.; Sibero, M. T.; Igarashi, Y.
    "Nocarimidazoles C and D, antimicrobial alkanoylimidazoles from a coral-derived actinomycete Kocuria sp.: application of 1JC,H coupling constants for the unequivocal determination of substituted imidazoles and stereochemical diversity of anteisoalkyl chains in microbial metabolites,"
    Beilstein J. Org. Chem., 2020, 16, 2719-2727. DOI:10.3762/bjoc.16.222
  • Saito, S.; Atsumi, K.; Zhou, T.; Fukaya, K.; Urabe, D.; Oku, N.; Karim, Md. R. U.; Komaki, H.; Igarashi, Y.
    "A cyclopeptide and three oligomycin-class polyketides produced by an underexplored actinomycete of the genus Pseudosporangium,"
    Beilstein J. Org. Chem., 2020, 16, 1100-1110. DOI:10.3762/bjoc.16.97
  • Fukaya, K.; Saito, A.; Nakajima, N.; Urabe, D.
    "A computational study on the intramolecular C4-C8ʹ interflavan bond formations of tethered catechin derivatives,"
    Bull. Chem. Soc. Jpn., 2020, 93, 1107-1113. DOI:10.1246/bcsj.20200094
  • Fukaya, K.; Saito, A.; Nakajima, N.; Urabe, D.
    "Computational analysis of the selective formation of the C4α-C8' bond in the intermolecular coupling of catechin derivatives,"
    J. Org. Chem., 2020, 85, 5010-5018. DOI:10.1021/acs.joc.0c00261
  • Yamashita, A.; Kishimoto, T.; Hamada, M.; Nakajima, N.; Urabe, D.​
    "Biomimetic Oxidation of Monolignol Acetate and p-Coumarate by Silver Oxide in 1,4-Dioxane,"
    J. Agric. Food Chem., 2020, 68, 2124-2131. DOI:10.1021/acs.jafc.9b07682
  • Fukaya, K.; Urabe, D.; Hiraizumi, M.; Noguchi, K.; Matsumoto, T.; Sakurai, K.
    "Computational and Experimental Analysis on the Conformational Preferences of Anticancer Saponin OSW-1,"
    J. Org. Chem., 2020, 85, 339-344. DOI:10.1021/acs.joc.9b02085
  • Kamakura, D.; Todoroki, H.; Urabe, D.; Hagiwara, K.; Inoue, M.​
    "Total Synthesis of Talatisamine,"
    Angew. Chem. Int. Ed., 2020, 59, 479-486. DOI:10.1002/anie.201912737
  • Fukaya, K.; Kono, Y.; Hibi, M.; Asano, Y.; Urabe, D.
    "A New Entry to the Synthesis of (±)-β-Lysine,"
    Heterocycles, 2020, 101, 701-706. DOI:10.3987/COM-19-S(F)38
  • Kishimoto, T.; Saito, M.; Suzuki, S.; Hamada, M.; Nakajima, N.; Urabe, D.​
    "Microwave-assisted direct transformation of​ lignocellulose into methyl glycopyranoside in​ ionic liquid,"
    Holzforschung, 2020, 74, 313–320. DOI:10.1515/hf-2019-0069


  • Sibero, M. T.; Zhou, T.; Fukaya, K.; Urabe, D.; Radjasa O. K.; Sabdono, A; Triant, A; Igarashi, Y.​
    "Two new aromatic polyketides from a sponge-derived Fusarium,"
    Beilstein J. Org. Chem., 2019, 15, 2941-2947. DOI:10.3762/bjoc.15.289
  • Kaneyama, T.; Fujimaru, K.; Takemura, M.; Hasegawa, K.; Hamada, M.; Kishimoto, T.; Urabe, D.; Nakajima, N.
    "Syntheic Study of an Intermediate Towards Paracentrone,"
    Heterocycles, 2019, 98, 281-294. DOI:10.3987/COM-18-S(F)91
  • Fukaya, K.; Saito, A.; Nakajima, N.; Urabe, D.
    "A Computational Study on the Stereo- and Regioselective Formation of the C4α-C6' Bond of Tethered Catechin Moieties by an Exhaustive Search of the Transition States,"
    J. Org. Chem., 2019, 84, 2840-2849. DOI:10.1021/acs.joc.8b03263


  • Urabe, D; Nakagawa, Y.; Mukai, K.; Fukushima, K.; Aoiki, N.; Itoh, H.; Nagatomo. M.; Inoue, M.
    "Total synthesis and biological evaluation of 19-hydroxysarmentogenin-3-O-alpha-L-rhamnoside, trewianin, and their aglycons,"
    J. Org. Chem., 2018, 83, 13888-13910. DOI:10.1021/acs.joc.8b02219
  • Saito, M.; Kishimoto, T.; Hamada, M.; Nakajima, N.; Urabe, D
    "A synergetic effect of ionic liquid and microwave irradiation on the acid-catalyzed direct conversion of cellulose into methyl glucopyranoside,"
    Holzforschung, 2018, 72, 1025-1030. DOI:10.1515/hf-2018-0020
  • Mochimaru, T.; Fukunaga, K.; Miyata, J.; Matsusaka, M.; Msaki, K.; Kabata, H.; Ueda, S.; Suzuki, Y.; Goto, T.; Urabe, D.; Inoue, M.; Isobe, Y.; Arita, M.; Betsuyaku, T.
    "12-OH-17,18-Epoxyeicosatetraenoic acid alleviates eosinophilic airway inflammation in murine lungs,"
    Allergy 2018, 73, 369-378. DOI:10.1111/all.13297
  • Sakata, K.; Wang, Y.; Urabe, D.; Inoue, M.
    "Synthesis of the tetracyclic structure of batrachotoxin enabled by bridgehead radical coupling and Pd/Ni-promoted Ullmann reaction,"
    Org. Lett. 2018, 20, 130-133. DOI:10.1021/acs.orglett.7b03482
  • Minagawa, K.; Urabe, D.; Inoue, M.
    "A three-component coupling approach to the ACE-ring substructure of C19-diterpene alkaloids,"
    J. Antibiotics 2018, 71, 326-332. DOI:10.1038/ja.2017.69


  • Hashimoto, S.; Katoh, S.; Kato, T.; Urabe, D.; Inoue, M.
    "Total synthesis of resiniferatoxin enabled by radical-mediated three-component coupling and 7-endo cyclization,"
    J. Am. Chem. Soc. 2017, 139, 16420-16429. DOI:10.1021/jacs.7b10177
  • Tao, J.; Kishimoto, T.; Hamada, M.; Nakajima, N.
    "Enzymatic synthesis of methyl β-D-glucoside directly from cellulose pretreated with bio-compatible amino acid ionic liquid/cosolvent,"
    Holzforschung 2017, 71, 21-26. DOI:10.1515/hf-2016-0091
  • Masuda, K.; Tanigawa, M.; Nagatomo, M.; Urabe, D.; M. Inoue,
    "Construction of carbocycles initiated by Cu-catalyzed radical reaction of Cl2C(CN)2,"
    Tetrahedron 2017, 73, 3596-3605. DOI:10.1016/j.tet.2017.03.063
  • Fujisawa, H.; Ishiyama, T.; Urabe, D.; Inoue, M.
    "Construction of the septahydroxylated ABC-ring system of dihydro-β-agarofurans: Application of 6-exo-dig radical cyclization,"
    Chem. Comm. 2017, 53, 4073-4076. DOI:10.1039/C7CC00507E