Publications | 成果報告

Articles | 論文

2022

  1. Matsumaru, T., Sueyoshi, K., Okubo, K., Fujii, S., Sakuratani, K., Saito, R., Ueki, K., Yamasaki, S., Fujimoto, Y. Trehalose diesters containing a polar functional group-modified lipid moiety: Synthesis and evaluation of Mincle-mediated signaling activity. Bioorg. Med. Chem. 2022, in press.

  2. Matsumaru, T., Sakuratani, K., Yanaka, S., Kato, K., Yamasaki, S., Fujimoto, Y. Fungal β-mannosyloxymannitol glycolipids and their analogues: synthesis and Mincle-mediated signaling activity. Eur. J. Org. Chem. 2022, e202200109. doi: 10.1002/ejoc.202200109

  3. Chang, T. C., Manabe, Y., Ito, K., Yamamoto, R., Kabayama, K., Ohshima, S., Kametani, Y., Fujimoto, Y., Lin, C. C., Fukase, K. Precise immunological evaluation rationalizes the design of a self-adjuvanting vaccine composed of glycan antigen, TLR1/2 ligand, and T-helper cell epitope. RSC Adv. 2022,12, 18985-18993. doi: 10.1039/D2RA03286D

    4. 2021

    1. Wang, Y., Hosomi, K., Shimoyama, A., Yoshii, K., Nagatake, T., Fujimoto, Y., Kiyono, H., Fukase, K., Kunisawa, J. Lipopolysaccharide derived from the lymphoid-resident commensal bacteria Alcaligenes faecalis functions as an effective nasal adjuvant to augment IgA antibody and Th17 cell responses. Front. Immunol. 2021, 12, 699349. doi: 10.3389/fimmu.2021.699349.

    2. Nuriya, M., Ashikari, Y., Shou, J., Iino, T., Asai, T., Karasawa, K., Nakamura, K., Ozeki, Y., Fujimoto, Y., Yasui, M. Alkyne-Tagged Dopamines as Versatile Analog Probes for Dopamin-ergic System Analysis. Anal. Chem. 2021, 93, 9345-9355. doi: 10.1021/acs.analchem.0c05403.

    3. Shimoyama A, Di Lorenzo F, Yamaura H, Mizote K, Palmigiano A, Pither MD, Speciale I, Uto T, Masui S, Sturiale L, Garozzo D, Hosomi K, Shibata N, Kabayama K, Fujimoto Y, Silipo A, Kunisawa J, Kiyono H, Molinaro A, Fukase K. Lipopolysaccharide from Gut-Associated Lymphoid-Tissue-Resident Alcaligenes faecalis: Complete Structure Determination and Chemical Synthesis of Its Lipid A. Angew Chem Int Ed Engl. 2021, 60, 10023-10031. doi: 10.1002/anie.202012374

      4. 2020

      1. Inuki S, Hirata N, Kashiwabara E, Kishi J, Aiba T, Teratani T, Nakamura W, Kojima Y, Maruyama T, Kanai T, Fujimoto Y. Polar functional group-containing glycolipid CD1d ligands modulate cytokine-biasing responses and prevent experimental colitis. Sci Rep. 2020 Sep 25;10(1):15766. doi: 10.1038/s41598-020-72280-4.

      2. Arai, Y., Torigoe, S., Matsumaru, T., Yamasaki, S., Fujimoto, Y. The key entity of a DCAR agonist, phosphatidylinositol mannoside Ac1PIM1: its synthesis and immunomodulatory function. Org. Biomol. Chem. 2020, 18, 3659-3663. doi: 10.1039/C9OB02724F

      3. Kusaka H, Kita S, Tadokoro T, Yoshida K, Kasai Y, Niiyama H, Fujimoto Y, Hanashima S, Murata M, Sugiyama S, Ose T, Kuroki K, Maenaka K. Efficient preparation of human and mouse CD1d proteins using silkworm baculovirus expression system. Protein Expr Purif. 2020, 172, 105631. doi: 10.1016/j.pep.2020.105631.

      4. Kishi, J., Inuki, S., Kashiwabara, E., Suzuki, T., Dohmae, N., Fujimoto, Y. Design and Discovery of Covalent α-GalCer Derivatives as Potent CD1d Ligands. ACS Chem. Biol. 2020, 15(2), 353-359. doi: 10.1021/acschembio.9b00700

        5. 2019

        1. Inuki, S., Sato, K., Zui, N., Yamaguchi, R., Matsumaru, T., Fujimoto, Y. Synthetic Studies on FNC-RED and Its Analogues Containing an All syn-Cyclopentanetetrol Moiety. J. Org. Chem. 2019, 84, 12680-12685. doi: 10.1021/acs.joc.9b02101.

          2019Funiculosin_JOC

        2. Kishi, J., Inuki, S., Hirata, N., Kashiwabara, E., Yoshidome, D., Ichihara, O., Fujimoto, Y. Structure-activity relationship studies of Bz amide-containing α-GalCer derivatives as natural killer T cell modulators. Bioorg. Med. Chem. Lett. 2019, 29, 970-973. doi: 10.1016/j.bmcl.2019.02.018.

          2019Kishi_BMCL

        3. Inuki, S., Fujimoto, Y. Total synthesis of naturally occurring chiral cyclopropane fatty acids and related compounds. Tetrahedron Lett. 2019, 60, 1083-1090. doi: 10.1016/j.tetlet.2019.03.043

          2019_inuki_TL

        4. Matsumaru, T., Ikeno, R., Shuchi, Y., Iwamatsu, T., Tadokoro, T., Yamasaki, S., Fujimoto, Y., Furukawa, A., Maenaka, K. Synthesis of glycerolipids containing simple linear acyl chains or aromatic rings and evaluation of their Mincle signaling activity. Chem. Comm. 2019, 55, 711-714. doi: 10.1039/c8cc07322h

          2019_matsumaru_CC

          5. 2018

          1. Inuki, S., Kashiwabara, E., Hirata, N., Kishi, J., Nabika, E., Fujimoto, Y. Potent Th2 Cytokine-Bias of Natural Killer T Cell by CD1d Glycolipid Ligands Based on "Anchoring Effect" of Polar Groups in Their Lipid Component. Angew. Chem. Int. Ed. 2018, 57, 9655-9659. doi: 10.1002/anie.201802983

            2018_GalCer_Th2

          2. Chang, T. C., Manabe, Y., Fujimoto, Y., Ohshima, S., Kametani, Y., Kabayama, K., Nimura, Y., Lin, C. C., Fukase, K. Syntheses and Immunological Evaluation of Self-Adjuvanting Clustered N-Acetyl and N-Propionyl Sialyl-Tn Combined with A T-helper Cell Epitope as Antitumor Vaccine Candidates. Angew. Chem. Int. Ed. 2018, 57, 8219-8224. doi: 10.1002/anie.201804437

            2018_synthetic_vaccine

          3. Arai, Y., Yokoyama, K., Kawahara, Y., Feng, Q., Ohta, I., Shimoyama, A., Inuki, S., Fukase, K., Kabayama, K., Fujimoto, Y. Time-lapse monitoring of TLR2 ligand internalization with newly developed fluorescent probes. Org. Biomol. Chem. 2018, 16, 3824-3830. doi: 10.1039/c7ob03205f

            2018_TLR2_live-cell

          4. Takeda, Y., Azuma, M., Hatsugai, R., Fujimoto, Y., Hashimoto, M., Fukase, K., Matsumoto, M., Seya, T. The second and third amino acids of Pam2 lipopeptides key for the proliferation of cytotoxic T cells. Innate Immunity 2018, 24, 323-331.

          5. Shibata, N., Kunisawa, J., Hosomi, K., Fujimoto, Y., Mizote, K., Kitayama, N., Shimoyama, A., Mimuro, H., Sato, S., Kishishita, N., Ishii, K. J., Fukase, K., Kiyono, H. Lymphoid tissue-resident Alcaligenes LPS induces IgA production without excessive inflammatory responses via weak TLR4 agonist activity. Mucosal Immunol. 2018, 11, 693-702. doi: 10.1038/mi.2017.103.

          6. Arai, Y., Inuki, S., Fujimoto, Y. Site-specific effect of polar functional group-modification in lipids of TLR2 ligands for modulating the ligand immunostimulatory activity. Bioorg. Med. Chem. Lett. 2018, 28, 1638-1641. doi: 10.1016/j.bmcl.2018.03.042

            2018_Arai_BMCL

          2017

          1. Inuki, S., Kishi, J., Kashiwabara, E., Aiba, T., Fujimoto, Y. Convergent Synthesis of Digalactosyl Diacylglycerols. Org. Lett., 2017, 19, 6482. doi: 10.1021/acs.orglett.7b03043.

            2017_DGDG

          2. Wang, Q., Marchetti, R., Prisic, S., Ishii, K., Arai, Y., Ohta, I., Inuki, S., Uchiyama, S., Silipo, A., Molinaro, A., Husson, R. N., Fukase, K., Fujimoto, Y. A Comprehensive Study of Interaction between Peptidoglycan Fragments and Extracelluar Domain of Mycobacterium tuberculosis Ser/Thr Kinase PknB. ChemBioChem. 2017, 18, 2094-2098. doi: 10.1002/cbic.201700385.

            20172017PGN-PknB

          3. Choy, S. L., Bernin, H., Aiba, T., Bifeld, E., Lender, S. C., Mühlenpfordt, M., Noll, J., Eick, J., Marggraff, C., Niss, H., Roldán, N. G., Tanaka, S., Kitamura, M., Fukase, K., Clos, J., Tannich, E., Fujimoto, Y., Lotter, H. Synthetic analogs of an Entamoeba histolytica glycolipid designed to combat intracellular Leishmania infection. Sci. Rep. 2017, 7: 9472. doi:10.1038/s41598-017-09894-8.

          4. Okamoto, N., Mizote, K., Honda, H., Saeki, A., Watanabe, Y., Yamaguchi-Miyamoto, T., Fukui, R., Tanimura, N., Motoi, Y., Akashi-Takamura, S., Kato, T., Fujishita, S., Kimura, T., Ohto, U., Shimizu, T., Hirokawa, T., Miyake, K., Fukase, K., Fujimoto, Y., Nagai, Y., Takatsu, K. Funiculosin variants and phosphorylated derivatives promote innate immune responses via the Toll-like receptor 4/myeloid differentiation factor-2 complex. J. Biol. Chem. 2017, 292, 15378-15394. doi: 10.1074/jbc.M117.791780.

          5. Inuki, S., Ohta, I., Ishibashi, S., Takamatsu, M., Fukase, K., Fujimoto, Y. Total Synthesis of Cardiolipins Containing Chiral Cyclopropane Fatty Acids. J. Org. Chem. 2017, 82, 7832-7838. doi: 10.1021/acs.joc.7b00945.

            2017Aiba

          6. Inuki, S., Aiba, T., Kawakami, S., Akiyama, T., Inoue, J. I., Fujimoto, Y. Chemical Synthesis of D-glycero-D-manno-Heptose 1,7-Bisphosphate and Evaluation of Its Ability to Modulate NF-κB Activation. Org. Lett. 2017, 19, 3079-3082. doi: 10.1021/acs.orglett.7b01158.

            2017Aiba

          7. Aiba, T., Suehara, S., Choy, S.-L., Maekawa, Y., Lotter, H., Murai, T., Inuki, S., Fukase, K., Fujimoto, Y. Employing BINOL-phosphoroselenoyl chloride for selective inositol phosphorylation and chemical synthesis of glycosyl inositol phospholipid from Entamoeba histolytica. Chem. Eur. J. 2017, 23, 8304-8308. doi: 10.1002/chem.201701298.

            2017Aiba

          8. Inuki, S., Sato, K., Fukuyama, T., Ryu, I., Fujimoto, Y. Formal Total Synthesis of L-Ossamine via Decarboxylative Functionalization Using Visible-Light-Mediated Photoredox Catalysisin a Flow System. J. Org. Chem. 2017, 82(2), 1248-1253. doi: 10.1021/acs.joc.6b02531.

            ossamine

          9. Wang,N., Hasegawa, H., Huang, C-y., Fukase, K., Fujimoto, Y., Synthesis of peptidoglycan fragments from Enterococcus faecalis with Fmoc-strategy for glycan elongation. Chem. Asian J. 2017, 12(1), 27-30. doi: 10.1002/asia.201601357

            2016NWang

          2016

          1. Shiokawa, Z., Kashiwabara, E., Yoshidome, D., Fukase, K., Inuki, S., Fujimoto, Y., Discovery of Novel Scaffold as Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitor Based on Pyrrolopiperazinone Alkaloid, Longamide B. ChemMedChem. 2016, 11(24), 2682-2689. doi: 10.1002/cmdc.201600446.

            2016Shiokawa_2

          2. Inuki, S., Aiba, T., Hirata, N., Ichihara, O., Yoshidome, D., Kita, S., Maenaka, K., Fukase, K., Fujimoto, Y., Isolated Polar Amino Acid Residues Modulate Lipid Binding in the Large Hydrophobic Cavity of CD1d. ACS Chem. Biol. 2016, 11(11), 3132-3139.  doi: 10.1021/6b00674

            2016Inuki_CD1d-amide

          3. Hashimoto, M., Ozono, M., Furuyashiki, M., Baba, R., Hashiguchi, S., Suda, Y., Fukase, K., Fujimoto, Y., Characterization of a novel D-glycero-D-talo-oct-2-ulosonic acid-substituted lipid a moiety in the lipopolysaccharide produced by the acetic acid bacterium Acetobacter pasteurianus NBRC 3283. J. Biol. Chem. 2016, 291(40), 21184-21194. doi: 10.1074/jbc.M116.751271

          4. Aiba, T., Sato, M., Umegaki, D., Iwasaki, T., Kambe, N., Fukase, K., Fujimoto, Y. Regioselective Phosphorylation of myo-Inositol with BINOL-Derived Phosphoramidites, and Its Application for Protozoan Lysophosphatidylinositol. Org. Biomol. Chem. 2016, 14, 6672-6675. doi: 10.1039/C6OB01062H.

            2016Aiba_OBC

          5. Wang, N., Hirata, A., Nokihara, K., Fukase, K., Fujimoto, Y., Peptidoglycan Microarray as A Novel Tool to Explore Protein-Ligand Recognition. Biopolymers. 2016, 106(4), 422-429 doi: 10.1002/bip.22807.

            2016NWang_array

          6. Wang, Q., Matsuo, Y., Pradipta, A. R., Inohara, N., Fujimoto, Y., Fukase, K., Synthesis of characteristic Mycobacterium peptidoglycan (PGN) fragments utilizing with chemoenzymatic preparation of meso-diaminopimelic acid (DAP), and their modulation of innate immune responses. Org. Biomol. Chem. 2016, 14, 1013-1023.

            2016QWang

          7. Shiokawa, Z., Inuki, S., Fukase, K., Fujimoto, Y., Efficient synthesis of (‒)-hanishin, (‒)-longamide B, and (‒)-longamide B Methyl Ester via piperazinone formation with 1,2-cyclic sulfamidates. Synlett. 2016, 27, 616-620.

            2016Shiokawa_1

          2015

          1. Inuki, S., Sato, K., Fujimoto, Y., Visible-light-mediated decarboxylative benzoyloxylation of β-hydroxy amino acids and its application to synthesis of functional 1,2-amino alcohol derivatives. Tetrahedron Lett. 2015, 56, 5787-5790.

          2. Aiba, T., Suehara, S., Bernin, H., Lotter, H., Inuki, S., Fukase, K., Fujimoto, Y. Synthesis and Biological Activity of Inositol Phospholipid as NKT Cell Modulator. Glycoconjugate J. 2015, 32, 301.

          3. Shimoyama, A., Mizote. K., Fujimoto, Y., Fukase, K. Synthesis and Biofunctional Study of Immunomodulative Lipopolysaccharide Partial Structures. Glycoconjugate J. 2015, 32, 310.

          4. Wang, Q., Matsuo, Y., Fujimoto, Y., Fukase, K. Synthesis and Function of Mycobacterium Cell Wall Peptidoglycan (PGN) Fragments. Peptide Science 2014, 51, 17-18.

          2014

          1. Mesnage, S., Dellarole, M., Baxter, N. J., Rouget, J-B., Dimitrov, J. D., Wang, N., Fujimoto, Y., Hounslow, A. M., Lacroix-Desmazes, S., Fukase, K., Foster, S. J. Williamson, M. P. Molecular basis for bacterial peptidoglycan recognition by LysM domains. Nat. Commun. 2014, 5:4269.

          2. Kadonaga, Y., Wang, N., Fujimoto, Y., Fukase, K Solid-phase Synthesis of Bacterial Cell Wall Peptidoglycan Fragments. Chem. Lett. 2014, 43(9), 1461-1463.

          3. Tanimura, N., Saitoh, S.I., Ohto, U., Fujimoto, Y., Fukase, K., Shimizu, T., Miyake, K. The attenuated inflammation of MPL is due to the lack of CD14-dependent tight dimerization of the TLR4/MD2 complex at the plasma membrane. Int. Immunol. 2014, 26(6), 307-14.

          4. Uchinashi, Y., Tanaka, K., Manabe, Y., Fujimoto, Y., Fukase, K. Practical and Efficient Method for α-Sialylation with an Azide Sialyl Donor Using a Microreactor. J. Carbohydrate Chem. 2014, 33(2), 55-67.

          5. Fujimoto, Y., Kajiki, Y., Kawahara, Y., Katsumoto M., Fukase, K. Bacterial Lipopeptides as Toll-Like Receptor 2 (TLR2) Ligands; Synthesis, Function and Its Application. Peptide Science 2014, 2013, 41-42.

          2013

          1. An, J. H., Kurokawa, K., Jung, D. J., Kim, M. J., Kim, C. H., Fujimoto, Y., Fukase, K., Coggeshall, K. M., Lee, B. L. Human SAP is a novel peptidoglycan recognition protein that induces complement-independent phagocytosis of Staphylococcus aureus. J. Immunol. 2013, 191, 3319-3327.

          2. Fujimoto, Y., Mitsunobe, K., Fujiwara, S., Mori, M., Hashimoto, M., Suda, Y., Kusumoto, S., Fukase, K. Synthesis and biological activity of phosphoglycolipids from Thermus thermophilus. Org. Bioorg. Chem. 2013, 11, 5034-5041.

          3. Hashimoto, M., Obara, K., Ozono, M., Furuyashiki, M., Ikeda, T., Suda, Y., Fukase, K., Fujimoto, Y., Shigehisa, H. Separation and characterization of the immunostimulatory components in unpolished rice black vinegar (kurozu). J. Biosci. Bioeng. 2013, 116 (6), 688-696.

          4. Fujimoto, Y., Shimoyama, A., Saeki, A., Kitayama, N., Kasamatsu, C., Tsutsui, H., Fukase, K. Innate immunomodulation by lipophilic termini of lipopolysaccharide; synthesis of lipid A from Porphyromonas gingivalis and other bacteria and their immunomodulative response. Mol. BioSyst. 2013, 9, 987-996.

          5. Iwasaki, T., Higashikawa, K., Reddy, V. P., Ho, W. W. S., Fujimoto, Y., Fukase, K., Terao, J., Kuniyasu, H., Kambe, N. Nickel-Butadiene Catalytic System for the Cross-Coupling of Bromoalkanoic Acids with Alkyl Grignard Reagents: A Practical and Versatile Method for Preparing Fatty Acids. Chem. Eur. J. 2013, 19, 2956-2960.

          6. Wang, N., Huang, C.-y., Hasegawa, M., Inohara, N., Fujimoto, Y., Fukase, K. Glycan sequence-dependent Nod2 activation investigated with chemically synthesized bacterial peptidoglycan fragment library. ChemBioChem. 2013, 14, 482-488.

          7. An, J.H., Kurokawa, K., Jung, D.J., Kim, M.J., Kim, C.H., Fujimoto, Y., Fukase, K., Coggeshall, K.M., Lee, B.L. Human SAP is a novel peptidoglycan recognition protein that induces complement-independent phagocytosis of Staphylococcus aureus. J. Immunol. 2013, 191(6), 3319-3327.

          2012

          1. Fujimoto, Y., Pradipta, A. R., Hashimoto, M., Kan, S., Shigehisa, H., Fukase, K. Peptidoglycan as Innate Immunomodulator; Chemical Synthesis of Its Fragments, Immunostimulatory Activities, and Natural Nod1 Ligand Structures in the Environments/Fermented Food. Peptide Science 2013, 97-98.

          2. Fujimoto, Y., Shimoyama, A., Suda, Y., Fukase, K. Synthesis and immunomodulatory activities of Helicobacter pylori lipophilic terminus of lipopolysaccharide including lipid A. Carbohydr. Res. 2012, 356, 37-43.

          3. Fukase, K., Fujimoto, Y., Shimoyama, A., Tanaka, K., Synthesis of Bacterial Glycoconjugates and Their Bio-functional Studies in Innate Immunity. J. Synth. Org. Chem. Jpn. 2012, 70, 113-130.

          4. Fujimoto, Y., Pradipta, A. R., Inohara, N., Fukase, K., Peptidoglycan as Nod1 ligand; Fragment structures in the environment, chemical synthesis, and their innate immunostimulation. Nat. Prod. Rep. 2012, 29, 568-579.

          2011

          1. Fujimoto, Y., Fukase, K., Structures, Synthesis, and Human Nod1 Stimulation of Immunostimulatory. Bacterial Peptidoglycan Fragments in the Environment. J. Nat. Prod. 2011, 74, 518-25.

          2. Shimoyama, A., Saeki, A., Tanimura, N., Tsutsui, H., Miyake, K., Suda, Y., Fujimoto, Y., Fukase. K., Chemical synthesis of Helicobacter pylori lipopolysaccharide partial structures and their selective proinflammatory response. Chem. Eur. J. 2011, 17, 14464-14474.

          3. Shimoyama, A., Fujimoto, Y., Fukase. K., Stereoselective glycosylation of 3-deoxy-D-manno-2-octulosonic acid (Kdo) with batch and microfluidic methods. Synlett 2011, 16, 2359-2362.

          4. Nishio, H., Kanno, S., Onoyama, S., Ikeda, K., Tanaka, T., Kusuhara, K., Fujimoto, Y., Fukase, K., Sueishi, K. Hara, T. Nod1 ligands induce site-specific vascular inflammation. Arterioscler. Thromb. Vasc. Biol. 2011, 31, 1093-1099.

          5. Sawahata, R., Shime, H., Yamazaki, S., Inoue, N., Akazawa, T., Fujimoto, Y., Fukase, K., Matsumoto, M., Seya, T. Failure of mycoplasma lipoprotein MALP-2 to induce NK cell activation through dendritic cell TLR2. Microbes Infect. 2011, 13, 350-358.

          2010

          1. Pradipta, A. R., Fujimoto, Y., Hasegawa, M., Inohara, N., Fukase, K. Characterization of natural human nucleotide-binding oligomerization domain protein 1 (NOD1) ligands from bacterial culture supernatant for elucidation of immune modulators in the environment. J. Biol. Chem. 2010, 285, 23607-23613.

          2. Huang, C-y., Wang, N., Fujiki, K., Otsuka, Y., Akamatsu, M., Fujimoto, Y., Fukase, K. Widely applicable deprotection method of 2,2,2-trichloroethoxycarbonyl (Troc) group using tetrabutylammonium fluoride. J. Carbohydr. Chem. 2010, 29, 289-298.

          3. Azuma, M., Sawahata R., Akao, Y., Ebihara, T., Yamazaki, S., Matsumoto, M., Hashimoto, M., Fukase, K., Fujimoto, Y., Seya, T. The peptide sequence of diacyl lipopeptides determines dendritic cell TLR2-mediated NK activation. PLos One 2010, 5(9), e12550.

          4. Asano, J., Tada, H., Onai, N., Sato, T., Horie, Y., Fujimoto, Y., Fukase, K., Suzuki, A., Mak, T. W., Ohteki, T. Nucleotide oligomerization binding domain-like receptor signaling enhances dendritic cell-mediated cross-priming in vivo. J. Immunol. 2010, 184(2), 736-45.

          5. Gutsmann, T., Howe, J., Zähringer, U., Garidel, P., Schromm, A. B., Koch, M.H., Fujimoto, Y., Fukase, K., Moriyon, I., Martínez-de-Tejada, G., Brandenburg, K. Structural prerequisites for endotoxic activity in the Limulus test as compared to cytokine production in mononuclear cells. Innate Immun. 2010, 16(1), 39-47.

          6. Bongat, A. F. G., Saksena, R., Adamo, R., Fujimoto, Y., Shiokawa, Z., Peterson, D. C., Fukase, K., Vann, W. F., Kováč, P. Multimeric bivalent immunogens from recombinant tetanus toxin HC fragment, synthetic hexasaccharides, and a glycopeptide adjuvant. Glycoconj. J. 2010, 27(1), 69-77.

          2009

          1. Fujimoto, Y., Hashimoto, M., Furuyashiki, M., Katsumoto, M., Seya, T., Suda, Y., Fukase, K. Lipopeptides from Staphylococcus aureus as Tlr2 Ligands: Prediction with mRNA Expression, Chemical Synthesis, and Immunostimulatory Activities. ChemBioChem. 2009, 10(14), 2311-2315.

          2. Fujimoto, Y., Konishi, Y., Kubo, O., Hasegawa, M., Inohara, N., Fukase. K. Synthesis of crosslinked peptidoglycan fragments for investigation of their immunobiological functions. Tetrahedron Lett. 2009, 50, 3631-3634.

          3. Katsumoto, M., Fujimoto, Y., Furuyashiki, M., Hashimoto, M., Suda, Y., and Fukase, K. Synthesis and immunostimulatory activities of lipopeptides from Gram-positive bacteria. Peptide Science 2008, 2009, 155-156.

          4. Tawaratsumida, K., Furuyashiki, M., Katsumoto, M., Fujimoto, Y., Fukase, K., Suda Y., Hashimoto, M. Characterization of N-terminal Structure of TLR2-activating Lipoprotein in Staphylococcus aureus. J. Biol. Chem. 2009, 284, 9147-9152.

          2008

          1. Kawasaki, A., Karasudani, Y., Otsuka, Y., Hasegawa, M., Inohara, N., Fujimoto, Y., Fukase, K. Synthesis of diaminopimelic acid-containing peptidoglycan fragments and tracheal cytotoxin (TCT) for investigation of their biological functions. Chem. Eur. J. 2008, 14, 10318-10330.

          2. Yano, T., Mita, S., Ohmori, H., Oshima, Y., Fujimoto, Y., Ueda, R., Takada, H., Goldman, W. E., Fukase, K., Silverman, N., Yoshimori, T., Kurata, S. Autophagic control of listeria through intracellular innate immune recognition in drosophila. Nat. Immunol. 2008, 9, 908-916.

          3. Fukase, Y., Fujimoto, Y., Adachi, Y., Suda, Y., Kusumoto, S., Fukase, K. Synthesis of Rubrivivax gelatinosus lipid A and analogues for investigation of the structural basis for immunostimulating and inhibitory activities. Bull. Chem. Soc. Japan. 2008, 81, 796-819. (Award Article)

          4. Hasegawa, M., Fujimoto, Y., Lucas, P. C., Nakano, H., Fukase, K., Nuñez, G., Inohara, N., A critical role of RICK/RIP2 polyubiquitination in Nod-induced NF-kappaB activation. EMBO J. 2008, 27, 373-383.

          5. Tohno, M., Shimazu, T., Aso, H., Uehara, A., Takada, H., Kawasaki, A., Fujimoto, Y., Fukase, K., Saito, T., Kitazawa, H., Molecular cloning and functional characterization of porcine nucleotide-binding oligomerization domain-1 (NOD1) recognizing minimum agonists, meso-diaminopimelic acid and meso-lanthionine. Mol. Immunol. 2008, 45, 1807-1817.

          6. Rallabhandi, P., Awomoyi, A., Thomas, K. E., Phalipon, A., Fujimoto, Y., Fukase, K., Kusumoto, S., Qureshi, N., Sztein, M. B., Vogel, S. N., Differential Activation of Human TLR4 by Escherichia coli and Shigella flexneri 2a Lipopolysaccharide: Combined Effects of Lipid A Acylation State and TLR4 Polymorphisms on Signaling. J. Immunol. 2008, 180, 1139-1147.

          2007

          1. Fujimoto, Y., Iwata, M., Imakita, N., Shimoyama, A., Suda, Y., Kusumoto, S., Fukase, K., Synthesis of immunoregulatory Helicobacter pylori lipopolysaccharide partial structures. Tetrahedron Lett. 2007, 48, 6577-6581.

          2. Fujimoto, Y., Inamura, S., Kawasaki, A., Shiokawa, Z., Shimoyama, A., Hashimoto, T., Kusumoto, S., Fukase, K., Chemical synthesis of peptidoglycan fragments for elucidation of the immunostimulating mechanism. J. Endotoxin Research 2007, 13, 189-196.

          3. Fujimoto, Y., Synthesis and functional analysis of the key compounds responsible for signal transduction. Yuki Gosei Kagaku Kyokaishi 2007, 65, 1170-1178.

          4. Uehara, A., Fujimoto, Y., Fukase, K., Takada, H., Various human epithelial cells express functional Toll-like receptors, NOD1 and NOD2 to produce anti-microbial peptides, but not proinflammatory cytokines. Mol. Immunol. 2007, 44, 3100-11.

          5. Park, J. H., Kim, Y. G., Shaw, M., Kanneganti, T. D., Fujimoto, Y., Fukase, K., Inohara, N., Nuñez, G., Nod1/RICK and TLR signaling regulate chemokine and antimicrobial innate immune responses in mesothelial cells. J. Immunol. 2007, 179, 514-521.

          6. Hashimoto, M., Furuyashiki, M., Kaseya, R., Fukada, Y., Akimaru, M., Aoyama, K., Okuno, T., Tamura, T., Kirikae, T., Kirikae, F., Eiraku, N., Morioka, H., Fujimoto, Y., Fukase, K., Takashige, K., Moriya, Y., Kusumoto, S., Suda, Y., Evidence of immunostimulating lipoprotein existing in the natural lipoteichoic acid fraction. Infect. Immun. 2007, 75, 1926-1932.

          7. Azuma, M., Matsuo, A., Fujimoto, Y., Fukase, K., Hazeki, O., Matsumoto, M., Seya, T., Inhibition of lipid A-mediated type I interferon induction by bactericidal/permeability-increasing protein (BPI). Biochem. Biophys. Res. Commun. 2007, 354, 574-578.

          8. Hasegawa, M., Kawasaki, A., Yang, K., Fujimoto, Y., Masumoto, J., Breukink, E., Nuñez, G., Fukase, K., Inohara, N., A role of lipophilic peptidoglycan-related molecules in induction of Nod1-mediated immune responses. J. Biol. Chem. 2007, 282, 11757-11764.

          9. Kawasaki, A., Karasudani, Y., Inohara, N., Fujimoto, Y., Fukase, K. Synthesis of meso-diaminopimelic acid for construction of gram-negative bacterial peptidoglycan partial structures. Peptide Science 2007, 44, 121-122

          2006

          1. Inamura, S., Fujimoto, Y., Kawasaki, A., Shiokawa, Z., Woelk, E., Heine, H., Lindner, B., Inohara, N., Kusumoto, S., Fukase, K., Synthesis of peptidoglycan fragments and evaluation of their biological activity. Org. Biomol. Chem. 2006, 4, 232-242.

          2. Hirota, S., Fujimoto, Y., Choi, J., Baden, N., Katagiri, N., Akiyama, M., Hulsker, R., Ubbink, M., Okajima, T., Takabe, T., Funasaki, N., Watanabe, Y., Terazima, M., Conformational Changes during Apoplastocyanin Folding Observed by Photocleavable Modification and Transient Grating. J. Am. Chem. Soc. 2006, 128, 7551-7558.

          3. Fujimoto, Y., Kimura, E., Murata, S., Kusumoto, S., Fukase, K., Synthesis and bioactivity of fluorescence- and biotin-labeled lipid A analogues for investigation of recognition mechanism in innate immunity. Tetrahedron Lett. 2006, 47, 539-543.

          4. Uehara, A., Fujimoto, Y., Kawasaki, A., Kusumoto, S., Fukase, K., Takada, H., Meso-Diaminopimelic Acid and meso-Lanthionine, Amino Acids Specific to Bacterial Peptidoglycans, Activates Human Epithelial Cells through NOD1. J. Immunol. 2006, 177, 1796-1804.

          5. Tanabe, T., Ishige, I., Suzuki, Y., Aita, Y., Furukawa, A., Ishige, Y., Uchida, K., Suzuki, T., Takemura, T., Ikushima, S., Oritsu, M., Yokoyama, T., Fujimoto, Y., Fukase, K., Inohara, N., Nuñez, G., Eishi, Y., Sarcoidosis and NOD1 variation with impaired recognition of intracellular Propionibacterium acnes. Biochim. Biophys. Acta 2006, 1762, 794-801.

          6. Sugawara, Y., Uehara, A., Fujimoto, Y., Kusumoto, S., Fukase, K., Shibata, K., Sugawara, S., Sasano, T., Takada, H., Toll-like Receptors, NOD1 and NOD2, in Oral Epithelial Cells. J. Dent. Res. 2006, 85, 524-529.

          7. Park, J. W., Je, B.-R., Piao, S., Inamura, S., Fujimoto, Y., Fukase, K., Kusumoto, S., Söderhäll, K., Ha, N.-C., Lee, B. L., A synthetic peptidoglycan fragment as a competitive inhibitor of the melanization cascade. J. Biol. Chem. 2006, 281, 7747-7755.

          8. Masumoto, J., Yang, K., Varambally, S., Hasegawa, M., Tomlins, S. A., Qiu, S., Fujimoto, Y., Kawasaki, A., Foster, S. J., Horie, Y., Mak, T. W., Nuñez, G., Chinnaiyan, A. M., Fukase, K., Inohara, N., Nod1 acts as an intracellular receptor to stimulate chemokine production and neutrophil recruitment in vivo. J. Exp. Med. 2006, 203, 203-13.

          9. Kobayashi, M., Saitoh, S., Tanimura, N., Takahashi, K., Kawasaki, K., Nishijima, M., Fujimoto, Y., Fukase, K., Akashi-Takamura, S., Miyake, K., Regulatory Roles for MD-2 and TLR4 in Ligand-Induced Receptor Clustering. J. Immunol. 2006, 176, 6211-8.

          10. Hasegawa, M., Yang, K., Hashimoto, M., Park, J. H., Kim, Y. G., Fujimoto, Y., Nuñez, G., Fukase, K., Inohara, N., Differential release and distribution of Nod1 and Nod2 immunostimulatory molecules among bacterial species and environments. J. Biol. Chem. 2006, 281, 29054-29063.

          11. Akamatsu, M., Fujimoto, Y., Kataoka, M., Suda, Y., Kusumoto, S., Fukase, K., Synthesis of lipid A monosaccharide analogues containing acidic amino acid: exploring the structural basis for the endotoxic and antagonistic activities. Bioorg. Med. Chem. 2006, 14, 6759-77.

          12. Shimoyama, A., Kawasaki, A., Inohara, N., Fujimoto, Y., Fukase, K., Synthesis of fluorescent probe for intracellular innate immune receptor Nod1. Peptide Science 2006, 43, 155.

          13. Kawasaki, A., Fujimoto, Y., Inohara, N., Fukase, K., Synthesis of potent immunostimulating Nod1 ligands: acylated diaminopimelic acid containing peptides. Peptide Science 2006, 43, 156.

          2005～2003

          1. Uehara, A., Yang, S., Fujimoto, Y., Fukase, K., Kusumoto, S., Shibata, K., Sugawara, S., Takada, H., Muramyldipeptide and diaminopimelic acid-containing desmuramylpeptides in combination with chemically synthesized toll-like receptor agonists synergistically induced production of interleukin-8 in a NOD2- and NOD1-dependent manner, respectively, in human monocytic cells in culture. Cell. Microbiol. 2005, 7, 53-61.

          2. Uehara, A., Sugawara, Y., Kurata, S., Fujimoto, Y., Fukase, K., Kusumoto, S., Satta, Y., Sasano, T., Sugawara, S., Takada, H., Chemically synthesized pathogen-associated molecular patterns increase the expression of peptidoglycan recognition proteins via toll-like receptors, NOD1 and NOD2 in human oral epithelial cells. Cell. Microbiol. 2005, 7, 675-686.

          3. Tokimoto, H., Fujimoto, Y., Fukase, K., Kusumoto, S., Stereoselective glycosylation using the long-range effect of a [2-(4-phenylbenzyl)oxycarbonyl]benzoyl group. Tetrahedron: Asymmetry 2005, 16, 441-447.

          4. Tanaka, S.-i., Takashina, M., Tokimoto, H., Fujimoto, Y., Tanaka, K., Fukase, K., Highly b-selective mannosylation towards Man-b-(1->4)-GlcNAc synthesis: TMSB(C6F5)4 as a lewis acid/cation trap catalyst. Synlett 2005, 2325-2328.

          5. Fukase, K., Inamura, S., Kawasaki, A., Fujimoto, Y., Kusumoto, S., Inohara, N., Nuñez, G., Mechanism of immunostimulating action of peptidoglycan, investigation with synthetic partial structures. Peptide Science 2005, 41, 109-112.

          6. Fujimoto, Y., Adachi, Y., Akamatsu, M., Fukase, Y., Kataoka, M., Suda, Y., Fukase, K., Kusumoto, S., Synthesis of lipid A and its analogues for investigation of the structural basis for their bioactivity. J. Endotoxin Research 2005, 11, 341-347.

          7. Cho, J. H., Fraser, I. P., Fukase, K., Kusumoto, S., Fujimoto, Y., Stahl, G. L., Ezekowitz, R. A. B., Human peptidoglycan recognition protein S is an effector of neutrophil-mediated innate immunity. Blood 2005, 106, 2551-2558.

          8. Fujimoto, Y., Inamura, S., Kawasaki, A., Kubo, O., Fukase, K., Kusumoto S. Synthesis of Peptidoglycan Partial Structures for Elucidation of the Mechanism of Its Immunostimulation. Biomolecular Chemistry -A Bridge for the Future-, 2003, 104-105.

          2002以前

          1. Fujimoto, Y., Xie, R., Tully, S. E., Berova, N., Nakanishi, K., Synthesis of 11-cis-locked bicyclo[5.1.0]octanyl retinal and an enantioselective binding to bovine opsin. Chirality 2002, 14, 340-346.

          2. Fujimoto, Y., Fishkin, N., Pescitelli, G., Decatur, J., Berova, N., Nakanishi, K., Solution and Biologically Relevant Conformations of Enantiomeric 11-cis-Locked Cyclopropyl Retinals. J. Am. Chem. Soc. 2002, 124, 7294-7302.

          3. Fujimoto, Y., Ishihara, J., Maki, S., Fujioka, N., Wang, T., Furuta, T., Fishkin, N., Borhan, B., Berova, N., Nakanishi, K., On the bioactive conformation of the rhodopsin chromophore: absolute sense of twist around the 6-s-cis bond. Chem. Euro. J. 2001, 7, 4198-4204.

          4. Sekine, C., Fujisawa, K., Fujimoto, Y., Minai, M., Optical anisotropy of phenylacetylene homologues. Mol. Cryst. Liq. Cryst. Sci. Technol. Sec A. 1999, 332, 2745-2752.

          5. Hashimoto, M., Fujimoto, Y., One step and convenient preparations of 4-hydroxyretinal and 4-oxoretinal. Synth. Commun. 1999, 29, 3793-3797.

          6. Ueda, K., Sekine, C., Tani, T., Fujisawa, K., Higashii, T., Kurimoto, I., Toda, S., Takano, N., Fujimoto, Y., Minai, M., Physical properties of novel biphenyl and phenylpyrimidine type ferroelectric liquid crystals. Ferroelectrics 1993, 148, 213-222.

          7. Sekine, C., Tani, T., Ueda, K., Fujisawa, K., Higashii, T., Kurimoto, I., Toda, S., Takano, N., Fujimoto, Y., Minai, M., Physical properties of new phenylpyrimidine type ferroelectric liquid crystals. Ferroelectrics 1993, 148, 203-212.

          8. Higashi, T., Kurimoto, I., Toda, S., Takano, N., Fujimoto, Y., Minai, M., Sekine, C., Tani, T., Ueda, K., Fujisawa, K., Synthesis and physical properties of new biphenyl and phenylpyrimidine type ferroelectric liquid crystals. Ferroelectrics 1993, 148, 169-178.

          9. Fukase, K., Kamikawa, T., Iwai, Y., Shiba, T., Rietschel, E. T., Kusumoto, S., Synthesis of allyl 3-deoxy-D-manno-2-octulopyranosidic acid 4- and 5-phosphates. Bull. Chem. Soc. Japan. 1991, 64, 3267-3273. (Y. Iwai is the former name of Y. Fujimoto)

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