論文 - 藤本　ゆかり

The key entity of a DCAR agonist, phosphatidylinositol mannoside Ac ₁PIM ₁: Its synthesis and immunomodulatory function

Arai Y., Torigoe S., Matsumaru T., Yamasaki S., Fujimoto Y.

Organic and Biomolecular Chemistry 18 （ 19 ） 3659 - 3663 2020年05月

査読有り,  ISSN  14770520

　概要を見る

© The Royal Society of Chemistry 2020. Ac1PIM1is a potential biosynthetic intermediate for phosphatidylinositol mannosides (PIMs) fromMycobacterium tuberculosis. We achieved the first synthesis of Ac1PIM1by utilizing an allyl-type protecting group strategy and regioselective phosphorylation of inositol. A very potent agonist of an innate immune receptor DCAR, which is better than previously known agonists, is demonstrated.

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Design and Discovery of Covalent α-GalCer Derivatives as Potent CD1d Ligands

Kishi J., Inuki S., Kashiwabara E., Suzuki T., Dohmae N., Fujimoto Y.

ACS Chemical Biology 15 （ 2 ） 353 - 359 2020年02月

査読有り,  ISSN  15548929

　概要を見る

© 2020 American Chemical Society. CD1d is a nonpolymorphic antigen-presenting protein responsible for the regulation of natural killer T (NKT) cell activation. α-Galactosyl ceramide (α-GalCer, KRN7000) is the representative CD1d ligand that can bind to the CD1d protein. The resulting complex is recognized by the T cell receptors of the NKT cell, inducing various immune responses. Previous structure-activity relationship studies of α-GalCer have revealed that the ability of NKT cells to induce cytokines depends on the ligand structure, and in particular, ligands that form more stable complexes with CD1d display potent activity. We focused on the Cys residue of the large hydrophobic pockets of CD1d (A′ pocket) and developed α-GalCer derivatives containing groups that can form covalent bonds. The assay results revealed that these ligands displayed higher levels of cytokine production and Th2 cell-type cytokine polarization response. Furthermore, the LC-MS/MS analysis indicated that the chloroacetylamide-containing ligand was covalently bound to Cys12 of CD1d, which suggests that the enhanced activities result from the formation of a stable CD1d-ligand complex. To our knowledge, this is the first ligand that allows covalent bond formation to CD1d under physiological conditions.

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Potent Th2 Cytokine-Bias of Natural Killer T Cell by CD1d Glycolipid Ligands Based on “Anchoring Effect” of Polar Groups in Their Lipid Component.

Inuki, S., Kashiwabara, E., Hirata, N., Kishi, J., Nabika, E., Fujimoto, Y.

Angew. Chem. Int. Ed. 57 （ 31 ） 9655 - 9659 2018年

研究論文（学術雑誌）, 共著, 査読有り,  ISSN  14337851

　概要を見る

© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Th2-biasing CD1d ligands are attractive potential candidates for adjuvants and therapeutic drugs. However, the number of potent ligands is limited, and their biasing mechanism remain unclear. Herein, a series of novel Th2-biasing CD1d glycolipid ligands, based on modification of their lipid part, have been identified. These have shown high binding affinities and efficient Th2 cytokine production. Importantly, the truncated acyl chain containing variants still retain their binding affinities and agonistic activities, which can be associated with an “anchoring effect,” that is, formation of a buried hydrogen bond between a polar group on the acyl chain and the CD1d lipid-binding pocket. The analysis indicated that the appearance rates of ligand–CD1d complexes on the cell surface were involved in Th2-biasing responses. The designed ligands, having the anchor in the shorter lipid part, are one of the most potent Th2-biasing ligands among the known ligands.

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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.

Chang, T. C., Manabe, Y., Fujimoto, Y., Ohshima, S., Kametani, Y., Kabayama, K., Nimura, Y., Lin, C. C., Fukase, K.

Angew. Chem. Int. Ed. （Angewandte Chemie - International Edition）  57 （ 27 ） 8219 - 8224 2018年

研究論文（学術雑誌）, 共著,  ISSN  14337851

　概要を見る

© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Sialyl-Tn (STn) is a tumor-associated carbohydrate antigen (TACA) rarely observed on healthy tissues. We synthesized two fully synthetic N-acetyl and N-propionyl STn trimer (triSTn) vaccines possessing a T-helper epitope and a TLR2 agonist, since the clustered STn antigens are highly expressed on many cancer cells. Immunization of both vaccines in mice induced the anti-triSTn IgG antibodies, which recognized triSTn-expressing cell lines PANC-1 and HepG2. The N-propionyl triSTn vaccine induced the triSTn-specific IgGs, while IgGs induced by the N-acetyl triSTn vaccine were less specific. These results illustrated that N-propionyl triSTn is a valuable unnatural TACA for anticancer vaccines.

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Isolated Polar Amino Acid Residues Modulate Lipid Binding in the Large Hydrophobic Cavity of CD1d

Inuki, S., Aiba, T., Hirata, N., Ichihara, O., Yoshidome, D., Kita, S., Maenaka, K., Fukase, K., Fujimoto, Y.

ACS Chem. Biol. 11   3132 - 3139 2016年09月

研究論文（学術雑誌）, 査読有り

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Trehalose diesters containing a polar functional group-modified lipid moiety: Synthesis and evaluation of Mincle-mediated signaling activity.

Matsumaru, T., Sueyoshi, K., Okubo, K., Fujii, S., Sakuratani, K., Saito, R., Ueki, K., Yamasaki, S., Fujimoto, Y.

Bioorg. Med. Chem. 75   117045 2022年12月

研究論文（学術雑誌）, 査読有り

Precise immunological evaluation rationalizes the design of a self-adjuvanting vaccine composed of glycan antigen, TLR1/2 ligand, and T-helper cell epitope.

Chang, T. C., Manabe, Y., Ito, K., Yamamoto, R., Kabayama, K., Ohshima, S., Kametani, Y., Fujimoto, Y., Lin, C. C., Fukase, K.

RSC Advances （The Royal Society of Chemistry）  12   18985 - 18993 2022年06月

研究論文（学術雑誌）, 査読有り

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β-mannosyloxymannitol glycolipids and their analogues: synthesis and Mincle-mediated signaling activity.

Matsumaru, T., Sakuratani, K., Yanaka, S., Kato, K., Yamasaki, S., Fujimoto, Y. Fungal

European journal of Organic Chemistry    e202200109 2022年04月

研究論文（学術雑誌）, 責任著者, 査読有り

Alkyne-Tagged Dopamines as Versatile Analog Probes for Dopamin-ergic System Analysis.

Nuriya, M., Ashikari, Y., Shou, J., Iino, T., Asai, T., Karasawa, K., Nakamura, K., Ozeki, Y., Fujimoto, Y.

Analytical Chemistry （ACS）  93 （ 27 ） 9345 - 9355 2021年07月

研究論文（学術雑誌）, 査読有り

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Lipopolysaccharide derived from the lymphoid-resident commensal bacteria Alcaligenes faecalis functions as an effective nasal adjuvant to augment IgA antibody and Th17 cell responses.

Wang, Y., Hosomi, K., Shimoyama, A., Yoshii, K., Nagatake, T., Fujimoto, Y., Kiyono, H., Fukase, K., Kunisawa, J.

Frontiers in immunology 12   699349 2021年07月

研究論文（学術雑誌）, 査読有り

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Lipopolysaccharide from Gut-Associated Lymphoid-Tissue-Resident Alcaligenes faecalis: Complete Structure Determination and Chemical Synthesis of Its Lipid A.

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.

Angew Chem Int Ed Engl 60 （ 18 ） 10023 - 10031 2021年01月

研究論文（学術雑誌）, 査読有り

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Polar functional group-containing glycolipid CD1d ligands modulate cytokine-biasing responses and prevent experimental colitis

Inuki S., Hirata N., Kashiwabara E., Kishi J., Aiba T., Teratani T., Nakamura W., Kojima Y., Maruyama T., Kanai T., Fujimoto Y.

Scientific Reports （Scientific Reports）  10 （ 1 ）  2020年12月

　概要を見る

The MHC class I-like molecule CD1d is a nonpolymorphic antigen-presenting glycoprotein, and its ligands include glycolipids, such as α-GalCer. The complexes between CD1d and ligands activate natural killer T cells by T cell receptor recognition, leading to the secretion of various cytokines (IFN-γ, IL-4, IL-17A, etc.). Herein, we report structure–activity relationship studies of α-GalCer derivatives containing various functional groups in their lipid acyl chains. Several derivatives have been identified as potent CD1d ligands displaying higher cytokine induction levels and/or unique cytokine polarization. The studies also indicated that flexibility of the lipid moiety can affect the binding affinity, the total cytokine production level and/or cytokine biasing. Based on our immunological evaluation and investigation of physicochemical properties, we chose bisamide- and Bz amide-containing derivatives 2 and 3, and evaluated their in vivo efficacy in a DSS-induced model of ulcerative colitis. The derivative 3 that exhibits Th2- and Th17-biasing responses, demonstrated significant protective effects against intestinal inflammation in the DSS-induced model, after a single intraperitoneal injection.

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Efficient preparation of human and mouse CD1d proteins using silkworm baculovirus expression system

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.

Protein Expression and Purification （Protein Expression and Purification）  172 2020年08月

ISSN  10465928

　概要を見る

© 2020 Elsevier Inc. CD1d is a major histocompatibility complex (MHC) class I-like glycoprotein and binds to glycolipid antigens that are recognized by natural killer T (NKT) cells. To date, our understanding of the structural basis for glycolipid binding and receptor recognition of CD1d is still limited. Here, we established a preparation method for the ectodomain of human and mouse CD1d using a silkworm-baculovirus expression system. The co-expression of human and mouse CD1d and β2-microglobulin (β2m) in the silkworm-baculovirus system was successful, but the yield of human CD1d was low. A construct of human CD1d fused with β2m via a flexible GS linker as a single polypeptide was prepared to improve protein yield. The production of this single-chained complex was higher (50 μg/larva) than that of the co-expression complex. Furthermore, differential scanning calorimetry revealed that the linker made the CD1d complex more stable and homogenous. These results suggest that the silkworm-baculovirus expression system is useful for structural and biophysical studies of CD1d in several aspects including low cost, easy handling, biohazard-free, rapid, and high yielding.

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Synthetic Studies on FNC-RED and Its Analogues Containing an All syn-Cyclopentanetetrol Moiety

Inuki, S., Sato, K., Zui, N., Yamaguchi, R., Matsumaru, T., Fujimoto, Y.

Journal of Organic Chemistry （Journal of Organic Chemistry）  84 （ 19 ） 12680 - 12685 2019年09月

研究論文（学術雑誌）, 査読有り,  ISSN  00223263

　概要を見る

© 2019 American Chemical Society. FNC-RED exhibits innate immune receptor Toll-like receptor 4 (TLR4)/myeloid differentiation factor-2 (MD2) stimulatory activity. We have developed a divergent synthetic route to FNC-RED derivatives containing various alkyl side chains. Key features of the synthetic study include stepwise palladium catalyzed cross-coupling reactions and the construction of an all syn-cyclopentanetetrol moiety.

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Total synthesis of naturally occurring chiral cyclopropane fatty acids and related compounds

Inuki S., Fujimoto Y.

Tetrahedron Letters （Tetrahedron Letters）  60 （ 16 ） 1083 - 1090 2019年04月

ISSN  00404039

　概要を見る

© 2019 Elsevier Ltd Cyclopropane fatty acids (CFAs) and related compounds containing CFAs commonly occur in various natural sources, including plants or microorganisms. Some CFAs exhibit intriguing biological activities such as antifungal or immunosuppressive activities. Due to their biological importance and structural features, a number of synthetic studies have been conducted to date. These total syntheses have helped to elucidate their structural determinants or biological activities. Herein the total syntheses of naturally occurring CFAs and related compounds are summarized.

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Structure-activity relationship studies of Bz amide-containing α-GalCer derivatives as natural killer T cell modulators

Kishi J., Inuki S., Hirata N., Kashiwabara E., Yoshidome D., Ichihara O., Fujimoto Y.

Bioorganic and Medicinal Chemistry Letters （Bioorganic and Medicinal Chemistry Letters）  29 （ 8 ） 970 - 973 2019年04月

ISSN  0960894X

　概要を見る

© 2019 Elsevier Ltd CD1d is a non-polymorphic antigen-presenting glycoprotein that recognizes glycolipids as ligands. Ligands bind to the hydrophobic grooves of CD1d, and the resulting ligand-CD1d complexes activate natural killer T (NKT) cells by means of T cell receptor recognition, leading to the secretion of various cytokines. However, details of the ligand recognition mechanism of a large hydrophobic ligand binding pocket and the relationship between cytokine induction and ligand structure are unclear. We report the synthesis of α-GalCer derivatives containing a Bz amide group having various substituting groups in the ceramide moiety, and the analysis of the structure-activity relationships. The assays reveal that the Bz amide-containing CD1d ligands function as NKT cell modulators displaying Th2 cytokine biasing responses. Furthermore, molecular dynamics simulation studies suggest that the phenyl groups can interact with the aromatic amino acid residues in the lipid binding pocket of CD1d.

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Glycans in infection and immunity

Suzuki T., Okamatsu M., Sakoda Y., Kinoshita T., Katayama T., Kiyono H., Goto Y., Takegawa K., Yokoyama N., Fujimoto Y., Angata T., Ohtani K., Wakamiya N., Arase H., Nishihara S., Suda Y.

Glycoscience: Basic Science to Applications: Insights from the Japan Consortium for Glycobiology and Glycotechnology (JCGG) （Glycoscience: Basic Science to Applications: Insights from the Japan Consortium for Glycobiology and Glycotechnology (JCGG)）     227 - 257 2019年01月

ISSN  9789811358555

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Synthesis of glycerolipids containing simple linear acyl chains or aromatic rings and evaluation of their Mincle signaling activity

Matsumaru T., Ikeno R., Shuchi Y., Iwamatsu T., Tadokoro T., Yamasaki S., Fujimoto Y., Furukawa A., Maenaka K.

Chemical Communications （Chemical Communications）  55 （ 5 ） 711 - 714 2019年

ISSN  13597345

　概要を見る

© The Royal Society of Chemistry. Mincle, expressed in activated phagocytes, recognizes the lipid ligand to activate the innate immune system. We have synthesized glycerol derivatives possessing simple alkyl chains or aromatic rings and elucidated their structure-activity relationships using a Mincle-mediated signaling assay. The activity depends on the length of the simple acyl chains of the glycerol derivatives.

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Synthesis of Cyclopropane Fatty Acids by C(sp3)–C(sp3) Cross-coupling Reaction and Formal Synthesis of α-Mycolic Acid.

Iwasaki, T., Terahigashi, S., Wang, Y., Tanaka, A., Zhao, H., Fujimoto, Y., Fukase, K., Kambe. N.

Adv. Synth. Catal. （Advanced Synthesis and Catalysis）  in press （ 19 ） 3810 - 3817 2018年

研究論文（学術雑誌）, 共著,  ISSN  16154150

　概要を見る

© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim An iterative Ni-catalyzed C(sp3)−C(sp3) cross-coupling reaction of a novel cis-cyclopropane containing bifunctional building blocks with alkyl halides and alkyl Grignard reagents enabled the introduction of a cyclopropane ring into the desired position(s) of saturated carbon frameworks, providing a straightforward synthetic route to cyclopropane fatty acids. The present method creates a direct route for the construction of saturated carbon frameworks, and can avoid the tedious multistep operations based on unsaturated functional group manipulations that are often employed in conventional synthetic routes. This method could be applicable to the synthesis of trans-cyclopropane fatty acids and enantioenriched cyclopropane fatty acids. Formal synthesis of α-mycolic acid was achieved by the C(sp3)−C(sp3) cross-coupling reaction of cyclopropane-containing bifunctional building blocks. (Figure presented.).

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Lymphoid tissue-resident Alcaligenes LPS induces IgA production without excessive inflammatory responses via weak TLR4 agonist activity.

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.

Mucosal Immunol. （Mucosal Immunology）  11 （ 3 ） 693 - 702 2018年

研究論文（学術雑誌）, 共著, 査読有り,  ISSN  19330219

　概要を見る

© The Author(s) 2018. Alcaligenes are opportunistic commensal bacteria that reside in gut-associated lymphoid tissues such as Peyer's patches (PPs); however, how they create and maintain their homeostatic environment, without inducing an excessive inflammatory response remained unclear. We show here that Alcaligenes-derived lipopolysaccharide (Alcaligenes LPS) acts as a weak agonist of toll-like receptor 4 and promotes IL-6 production from dendritic cells, which consequently enhances IgA production. The inflammatory activity of Alcaligenes LPS was weaker than that of Escherichia coli-derived LPS and therefore no excessive inflammation was induced by Alcaligenes LPS in vitro or in vivo. Alcaligenes LPS also showed adjuvanticity, inducing antigen-specific immune responses without excessive inflammation. These findings reveal the presence of commensal bacteria-mediated homeostatic inflammatory conditions within PPs that produce optimal IgA induction without causing pathogenic inflammation and suggest that Alcaligenes LPS could be a safe and potent adjuvant.

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Site-specific effect of polar functional group-modification in lipids of TLR2 ligands for modulating the ligand immunostimulatory activity.

Arai, Y., Inuki, S., Fujimoto, Y.

Bioorg Med Chem Lett. （Bioorganic and Medicinal Chemistry Letters）  28 （ 9 ） 1638 - 1641 2018年

研究論文（学術雑誌）, 共著, 査読有り,  ISSN  0960894X

　概要を見る

© 2018 Elsevier Ltd Toll-like receptor 2 (TLR2), a member of the TLR innate immune receptor family, recognizes lipoproteins from bacteria and modulates the immune response by inducing the expression of various cytokines. TLR2 has a large hydrophobic pocket that recognizes long fatty acyl groups on TLR2 ligands. However, few studies have focused on the property of the hydrophobic TLR2 pocket. Based on the X-ray crystal structure of TLR2, small polar regions were found in the hydrophobic TLR2 pocket. Interactions between the polar residues and ligands were explored here by designing and synthesizing a Pam2CSK4 derivative of the TLR2 ligands, containing an amide group within the lipid moiety. We evaluated the binding affinities and immunomodulatory activities of these ligands. Results suggested that the amide groups in the lipid chain interacted with the polar residues in the hydrophobic lipid-binding pocket of TLR2.

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Time-lapse monitoring of TLR2 ligand internalization with newly developed fluorescent probes.

Arai, Y., Yokoyama, K., Kawahara, Y., Feng, Q., Ohta, I., Shimoyama, A., Inuki, S., Fukase, K., Kabayama, K., Fujimoto, Y.

Org. Biomol. Chem. （Organic and Biomolecular Chemistry）  16 （ 20 ） 3824 - 3830 2018年

研究論文（学術雑誌）, 共著,  ISSN  14770520

　概要を見る

© 2018 The Royal Society of Chemistry. As a mammalian toll-like receptor family member protein, TLR2 recognizes lipoproteins from bacteria and modulates the immune response by inducing the expression of various cytokines. We have developed fluorescence-labeled TLR2 ligands with either hydrophilic or hydrophobic fluorescence groups. The labeled ligands maintained the inflammatory IL-6 induction activity and enabled us to observe the internalization and colocalization of the TLR2 ligands using live-cell imaging. The time-lapse monitoring in the live-cell imaging of the fluorescence-labeled TLR2 ligand showed that TLR2/CD14 expression in the host cells enhanced the internalization of TLR2 ligand molecules.

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The second and third amino acids of Pam2 lipopeptides key for the proliferation of cytotoxic T cells.

Takeda, Y., Azuma, M., Hatsugai, R., Fujimoto, Y., Hashimoto, M., Fukase, K., Matsumoto, M., Seya, T.

Innate Immunity （Innate Immunity）  24 （ 5 ） 323 - 331 2018年

研究論文（学術雑誌）, 共著,  ISSN  17534259

　概要を見る

© The Author(s) 2018. The TLR2 agonist, dipalmitoyl lipopeptide (Pam2LP), has been used as an immune adjuvant without much success. Pam2LP is recognised by TLR2/6 receptors in humans and in mice. This study examined the proliferative activity of cytotoxic T lymphocytes (CTL) using mouse Ag-presenting dendritic cells (DCs) and OT-I assay system, where a library of synthetic Pam2LP was utilised from the Staphylococcus aureus database. Ag-specific CTL expansion and IFN-γ levels largely depended on the Pam2LP peptide sequence. The first Aa is cysteine (Cys), which has an active SH residue to bridge fatty acids, and the second and third Aa are hydrophilic or non-polar. The sequence structurally adapted to the residual constitution of the reported TLR2/6 pocket. The inactive sequence contained proline or leucine/isoleucine after the first Cys. Notably, no direct activation of OT-I cells was detected without DCs by stimulation with the active Pam2LP having the Cys-Ser sequence. MyD88, but not TICAM-1 or IFN pathways, in DCs participates in DC maturation characterised by upregulation of CD40, CD80 and CD86. Hence, the active Pam2LPs appear suitable for dimeric TLR2/6 on DCs, resulting in induction of DC maturation.

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Employing BINOL-phosphoroselenoyl chloride for selective inositol phosphorylation and chemical synthesis of glycosyl inositol phospholipid from Entamoeba histolytica.

Aiba, T., Suehara, S., Choy, S.-L., Maekawa, Y., Lotter, H., Murai, T., Inuki, S., Fukase, K., Fujimoto, Y.

Chem. Eur. J. 23   8304 - 8308 2017年04月

研究論文（学術雑誌）, 共著, 査読有り

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Formal Total Synthesis of L-Ossamine via Decarboxylative Functionalization Using Visible-Light-Mediated Photoredox Catalysisin a Flow System

Inuki, S., Sato, K., Fukuyama, T., Ryu, I., Fujimoto, Y.

J. Org. Chem. 82 （ 2 ） 1248 - 1253 2017年01月

研究論文（学術雑誌）, 査読有り

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Synthesis of Peptidoglycan Fragments from Enterococcus faecalis with Fmoc-Strategy for Glycan Elongation.

Wang, N., Hasegawa, H., Huang, CY., Fukase, K., Fujimoto, Y.

Chem Asian J. 12 （ 1 ） 27 - 30 2017年01月

研究論文（学術雑誌）

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Convergent Synthesis of Digalactosyl Diacylglycerols.

Inuki, S., Kishi, J., Kashiwabara, E., Aiba, T., Fujimoto, Y.

Org. Lett. 19   6482 2017年

研究論文（学術雑誌）, 共著, 査読有り

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Funiculosin variants and phosphorylated derivatives promote innate immune responses via the Toll-like receptor 4/myeloid differentiation factor-2 complex.

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.

J. Biol. Chem. 292 （ 37 ） 15378 - 15394 2017年

研究論文（学術雑誌）, 共著, 査読有り

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A Comprehensive Study of the Interaction between Peptidoglycan Fragments and the Extracellular Domain of Mycobacterium tuberculosis Ser/Thr Kinase PknB.

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.

ChemBioChem 18   2094 - 2098 2017年

研究論文（学術雑誌）, 共著, 査読有り

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Chemical Synthesis of D-glycero-D-manno-Heptose 1,7-Bisphosphate and Evaluation of Its Ability to Modulate NF-κB Activation.

Inuki, S., Aiba, T., Kawakami, S., Akiyama, T., Inoue, J. I., Fujimoto, Y.

Org. Lett. 19 （ 12 ） 3079 - 3082 2017年

研究論文（学術雑誌）, 共著, 査読有り

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Total Synthesis of Cardiolipins Containing Chiral Cyclopropane Fatty Acids.

Inuki, S., Ohta, I., Ishibashi, S., Takamatsu, M., Fukase, K., Fujimoto, Y.

J. Org. Chem. 82 （ 15 ） 7832 - 7838 2017年

研究論文（学術雑誌）, 共著, 査読有り

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Synthetic analogs of a protozoan glycolipid designed to combat intracellular Leishmania infection.

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.

Sci. Rep. 7   9472 2017年

研究論文（学術雑誌）, 共著, 査読有り

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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.

Hashimoto, M., Ozono, M., Furuyashiki, M., Baba, R., Hashiguchi, S., Suda, Y., Fukase, K., Fujimoto, Y.

J. Biol. Chem. 291 （ 40 ） 21184 - 21194 2016年09月

研究論文（学術雑誌）, 査読有り

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Synthesis of characteristic Mycobacterium peptidoglycan (PGN) fragments utilizing with chemoenzymatic preparation of meso-diaminopimelic acid (DAP), and their modulation of innate immune responses

Wang, Q., Matsuo, Y., Pradipta, A. R., Inohara, N., Fujimoto, Y., Fukase, K.

Org. Biomol. Chem. 14   1013 - 1023 2016年01月

研究論文（学術雑誌）, 査読有り

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Efficient synthesis of (‒)-hanishin, (‒)-longamide B, and (‒)-longamide B Methyl Ester via piperazinone formation with 1,2-cyclic sulfamidates

Shiokawa, Z., Inuki, S., Fukase, K., Fujimoto, Y.

Synlett 27 （ 4 ） 616 - 620 2016年01月

研究論文（学術雑誌）, 共著, 査読有り

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Peptidoglycan Microarray as A Novel Tool to Explore Protein-Ligand Recognition

Wang, N., Hirata, A., Nokihara, K., Fukase, K., Fujimoto, Y.

Biopolymers 106 （ 4 ） 422 - 429 2016年

研究論文（学術雑誌）

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Regioselective Phosphorylation of myo-Inositol with BINOL-Derived Phosphoramidites, and Its Application for Protozoan Lysophosphatidylinositol

Aiba, T., Sato, M., Umegaki, D., Iwasaki, T., Kambe, N., Fukase, K. Fujimoto, Y.

Org. Biomol. Chem. 14   6672 - 6675 2016年

研究論文（学術雑誌）, 査読有り

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Discovery of a Novel Scaffold as an Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitor Based on the Pyrrolopiperazinone Alkaloid, Longamide B.

Shiokawa, Z., Kashiwabara, E., Yoshidome, D., Fukase, K., Inuki, S., Fujimoto, Y.

ChemMedChem. 11 （ 24 ） 2682 - 2689 2016年

研究論文（学術雑誌）, 査読有り

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Visible-light-mediated decarboxylative benzoyloxylation of β-hydroxy amino acids and its application to synthesis of functional 1,2-amino alcohol derivatives

Inuki, S., Sato, K., Fujimoto, Y.

Tetrahedron Lett. 56   5787 - 5790 2015年09月

研究論文（学術雑誌）, 共著, 査読有り

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Synthesis and Biological Activity of Inositol Phospholipid as NKT Cell Modulator.

Aiba, T., Suehara, S., Bernin, H., Lotter, H., Inuki, S., Fukase, K., Fujimoto, Y.

Glycoconjugate J. 32   301 2015年

研究論文（国際会議プロシーディングス）, 共著

Synthesis and Biofunctional Study of Immunomodulative Lipopolysaccharide Partial Structures.

Shimoyama, A., Mizote. K., Fujimoto, Y., Fukase, K.

Glycoconjugate J. 32   310 2015年

研究論文（国際会議プロシーディングス）, 共著

Synthesis and Function of Mycobacterium Cell Wall Peptidoglycan (PGN) Fragments.

Wang, Q., Matsuo, Y., Fujimoto, Y., Fukase, K.

Peptide Science 2014   17 2015年

研究論文（国際会議プロシーディングス）, 共著

Bacterial glycoconjugates; chemical synthesis and functional analysis

Fujimoto, Yukari

Glycobiology 24 （ 11 ） 1086 - 1086 2014年11月

研究論文（学術雑誌）,  ISSN  0959-6658

Molecular basis for bacterial peptidoglycan recognition by LysM domains

Mesnage, Stephane, Dellarole, Mariano, Baxter, Nicola J., Rouget, Jean-Baptiste, Dimitrov, Jordan D., Wang, Ning, Fujimoto, Yukari, Hounslow, Andrea M., Lacroix-Desmazes, Sebastien, Fukase, Koichi, Foster, Simon J., Williamson, Michael P.

Nat. Commun. 5   4269 2014年06月

研究論文（学術雑誌）,  ISSN  2041-1723

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Solid-phase Synthesis of Bacterial Cell Wall Peptidoglycan Fragments

Kadonaga, Yuichiro, Wang, Ning, Fujimoto, Yukari, Fukase, Koichi

Chem. Lett. 43 （ 9 ） 1461 - 1463 2014年05月

研究論文（学術雑誌）,  ISSN  0366-7022

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Bacterial Lipopeptides as Toll-Like Receptor 2 (TLR2) Ligands; Synthesis, Function and Its Application

Fujimoto, Y., Kajiki, Y., Kawahara, Y., Katsumoto M., Fukase, K.

Peptide Science 2013   41 - 42 2014年04月

研究論文（国際会議プロシーディングス）

Practical and efficient method for α-sialylation with an azide sialyl donor using a microreactor

Yosuke Uchinashi; Katsunori Tanaka; Yoshiyuki Manabe; Yukari Fujimoto; Koichi Fukase

Journal of Carbohydrate Chemistry 33 （ 2 ） 55 - 67 2014年02月

研究論文（学術雑誌）

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The attenuated inflammation of MPL is due to the lack of CD14-dependent tight dimerization of the TLR4/MD2 complex at the plasma membrane

Natsuko Tanimura; Shin-Ichiroh Saitoh; Umeharu Ohto; Sachiko Akashi-Takamura; Yukari Fujimoto; Koichi Fukase; Toshiyuki Shimizu; Kensuke Miyake

International Immunology 26 （ 6 ） 307 - 314 2014年

研究論文（学術雑誌）

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Separation and characterization of the immunostimulatory components in unpolished rice black vinegar (kurozu)

Hashimoto, Masahito, Obara, Kyoko, Ozono, Mami, Furuyashiki, Maiko, Ikeda, Tsuyoshi, Suda, Yasuo, Fukase, Koichi, Fujimoto, Yukari, Shigehisa, Hiroshi

JOURNAL OF BIOSCIENCE AND BIOENGINEERING 116 （ 6 ） 688 - 696 2013年12月

研究論文（学術雑誌）,  ISSN  1389-1723

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Human SAP is a novel peptidoglycan recognition protein that induces complement-independent phagocytosis of Staphylococcus aureus

Jang-Hyun An; Kenji Kurokawa; Dong-Jun Jung; Min-Jung Kim; Chan-Hee Kim; Yukari Fujimoto; Koichi Fukase; K. Mark Coggeshall; Bok Luel Lee

Journal of Immunology 191 （ 6 ） 3319 - 3327 2013年09月

研究論文（学術雑誌）

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Synthesis and biological activity of phosphoglycolipids from Thermus thermophilus

Fujimoto, Yukari, Mitsunobe, Kunihiro, Fujiwara, Satoko, Mori, Motoko, Hashimoto, Masahiro, Suda, Yasuo, Kusumoto, Shoichi, Fukase, Koichi

ORGANIC & BIOMOLECULAR CHEMISTRY 11 （ 30 ） 5034 - 5041 2013年08月

研究論文（学術雑誌）,  ISSN  1477-0520

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Glycan Sequence-Dependent Nod2 Activation Investigated by Using a Chemically Synthesized Bacterial Peptidoglycan Fragment Library

Ning Wang; Cheng-Yuan Huang; Mizuho Hasegawa; Naohiro Inohara; Yukari Fujimoto; Koichi Fukase

ChemBioChem 14 （ 4 ） 482 - 488 2013年03月

研究論文（学術雑誌）

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Nickel-Butadiene Catalytic System for the Cross-Coupling of Bromoalkanoic Acids with Alkyl Grignard Reagents: A Practical and Versatile Method for Preparing Fatty Acids

Iwasaki, Takanori, Higashikawa, Kiyokazu, Reddy, Vutukuri P., Ho, Willbe W. S., Fujimoto, Yukari, Fukase, Koichi, Terao, Jun, Kuniyasu, Hitoshi, Kambe, Nobuaki

CHEMISTRY-A EUROPEAN JOURNAL 19 （ 9 ） 2956 - 2960 2013年02月

研究論文（学術雑誌）,  ISSN  0947-6539

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Innate immunomodulation by lipophilic termini of lipopolysaccharide; synthesis of lipid As from Porphyromonas gingivalis and other bacteria and their immunomodulative responses

Fujimoto, Yukari, Shimoyama, Atsushi, Saeki, Akinori, Kitayama, Naohiro, Kasamatsu, Chika, Tsutsui, Hiroko, Fukase, Koichi

MOLECULAR BIOSYSTEMS 9 （ 5 ） 987 - 996 2013年

研究論文（学術雑誌）,  ISSN  1742-206X

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Synthesis and immunomodulatory activities of Helicobacter pylori lipophilic terminus of lipopolysaccharide including lipid A

Fujimoto, Yukari, Shimoyama, Atsushi, Suda, Yasuo, Fukase, Koichi

CARBOHYDRATE RESEARCH 356   37 - 43 2012年07月

研究論文（学術雑誌）,  ISSN  0008-6215

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Synthesis of Bacterial Glycoconjugates and Their Bio-functional Studies in Innate Immunity

Fukase, Koichi, Fujimoto, Yukari, Shimoyama, Atsushi, Tanaka, Katsunori

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN 70 （ 2 ） 113 - 130 2012年02月

研究論文（学術雑誌）,  ISSN  0037-9980

Peptidoglycan as Innate Immunomodulator; Chemical Synthesis of Its Fragments, Immunostimulatory Activities, and Natural Nod1 Ligand Structures in the Environments/Fermented Food.

FUJIMOTO YUKARI

Peptide Science,    97 - 98 2012年

研究論文（国際会議プロシーディングス）

Peptidoglycan as Nod1 ligand; fragment structures in the environment, chemical synthesis, and their innate immunostimulation

Fujimoto, Yukari, Pradipta, Ambara Rachmat, Inohara, Naohiro, Fukase, Koichi

NATURAL PRODUCT REPORTS 29 （ 5 ） 568 - 579 2012年

研究論文（学術雑誌）,  ISSN  0265-0568

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Chemical Synthesis of helicobacter pylori lipopolysaccharide partial structures and their selective proinflammatory responses

Atsushi Shimoyama; Akinori Saeki; Natsuko Tanimura; Hiroko Tsutsui; Kensuke Miyake; Yasuo Suda; Yukari Fujimoto; Koichi Fukase

Chemistry - A European Journal 17 （ 51 ） 14464 - 14474 2011年12月

研究論文（学術雑誌）

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Stereoselective Glycosylation of 3-Deoxy-D-manno-2-octulosonic Acid with Batch and Microfluidic Methods

Shimoyama, Atsushi, Fujimoto, Yukari, Fukase, Koichi

SYNLETT  （ 16 ） 2359 - 2362 2011年10月

研究論文（学術雑誌）,  ISSN  0936-5214

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Nod1 Ligands Induce Site-Specific Vascular Inflammation

Nishio, Hisanori, Kanno, Shunsuke, Onoyama, Sagano, Ikeda, Kazuyuki, Tanaka, Tamami, Kusuhara, Koichi, Fujimoto, Yukari, Fukase, Koichi, Sueishi, Katsuo, Hara, Toshiro

ARTERIOSCLEROSIS THROMBOSIS AND VASCULAR BIOLOGY 31 （ 5 ） 1093 - U383 2011年05月

研究論文（学術雑誌）,  ISSN  1079-5642

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Failure of mycoplasma lipoprotein MALP-2 to induce NK cell activation through dendritic cell TLR2

Sawahata, Ryoko, Shime, Hiroaki, Yamazaki, Sayuri, Inoue, Norimitsu, Akazawa, Takashi, Fujimoto, Yukari, Fukase, Koichi, Matsumoto, Misako, Seya, Tsukasa

MICROBES AND INFECTION 13 （ 4 ） 350 - 358 2011年04月

研究論文（学術雑誌）,  ISSN  1286-4579

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Structures, Synthesis, and Human Nod1 Stimulation of Immunostimulatory Bacterial Peptidoglycan Fragments in the Environment

Fujimoto, Yukari, Fukase, Koichi

J. Nat. Prod. 74 （ 3 ） 518 - 525 2011年03月

研究論文（学術雑誌）,  ISSN  0163-3864

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The Peptide Sequence of Diacyl Lipopeptides Determines Dendritic Cell TLR2-Mediated NK Activation

Azuma, Masahiro, Sawahata, Ryoko, Akao, Yuusuke, Ebihara, Takashi, Yamazaki, Sayuri, Matsumoto, Misako, Hashimoto, Masahito, Fukase, Koichi, Fujimoto, Yukari, Seya, Tsukasa

PLOS ONE 5 （ 9 ） 688 - 696 2010年09月

研究論文（学術雑誌）,  ISSN  1932-6203

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Multimeric bivalent immunogens from recombinant tetanus toxin H-C fragment, synthetic hexasaccharides, and a glycopeptide adjuvant

Bongat, Aileen F. G., Saksena, Rina, Adamo, Roberto, Fujimoto, Yukari, Shiokawa, Zenyu, Peterson, Dwight C., Fukase, Koichi, Vann, Willie F., Kovac, Pavol

GLYCOCONJUGATE JOURNAL 27 （ 1 ） 69 - 77 2010年01月

研究論文（学術雑誌）,  ISSN  0282-0080

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Nucleotide Oligomerization Binding Domain-Like Receptor Signaling Enhances Dendritic Cell-Mediated Cross-Priming In Vivo

Asano, Jumpei, Tada, Hiroyuki, Onai, Nobuyuki, Sato, Taku, Horie, Yasuo, Fujimoto, Yukari, Fukase, Koichi, Suzuki, Akira, Mak, Tak W., Ohteki, Toshiaki

JOURNAL OF IMMUNOLOGY 184 （ 2 ） 736 - 745 2010年01月

研究論文（学術雑誌）,  ISSN  0022-1767

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“プロバイオティクス有用性の分子基盤解明−腸内細菌の自然免疫活性化因子の単離と構造解析−”

藤本 ゆかり

IFO. Res. Commun. 81 （ 91 ）  2010年

研究論文（その他学術会議資料等）

SELF AND NONSELF RECOGNITION WITH BACTERIAL AND ANIMAL GLYCANS, SURVEYS BY SYNTHETIC CHEMISTRY

Fujimoto, Yukari, Tanaka, Katsunori, Shimoyama, Atsushi, Fukase, Koichi

METHODS IN ENZYMOLOGY, VOL 478: GLYCOMICS 478   323 - 342 2010年

研究論文（学術雑誌）,  ISSN  0076-6879

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Characterization of natural human nucleotide-binding oligomerization domain protein 1 (NOD1) ligands from bacterial culture supernatant for elucidation of immune modulators in the environment.

Pradipta, A. R., Fujimoto, Y., Hasegawa, M., Inohara, N., Fukase, K.

J. Biol. Chem. 285 （ 31 ） 23607 - 23613 2010年

研究論文（学術雑誌）, 査読有り

Widely applicable deprotection method of 2,2,2-trichloroethoxycarbonyl (Troc) group using tetrabutylammonium fluoride.

Huang, C-y., Wang, N., Fujiki, K., Otsuka, Y., Akamatsu, M., Fujimoto, Y., Fukase, K.

J. Carbohydr. Chem. 29 （ 1 ） 1 - 9 2010年

研究論文（学術雑誌）, 査読有り

Structural prerequisites for endotoxic activity in the Limulus test as compared to cytokine production in mononuclear cells.

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.

Innate Immun. 16 （ 1 ） 39 - 47 2010年

研究論文（学術雑誌）, 査読有り

Lipopeptides from Staphylococcus aureus as Tlr2 Ligands: Prediction with mRNA Expression, Chemical Synthesis, and Immunostimulatory Activities

Fujimoto, Yukari, Hashimoto, Masahito, Furuyashiki, Maiko, Katsumoto, Mami, Seya, Tsukasa, Suda, Yasuo, Fukase, Koichi

CHEMBIOCHEM 10 （ 14 ） 2311 - 2315 2009年09月

研究論文（学術雑誌）,  ISSN  1439-4227

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Synthesis of crosslinked peptidoglycan fragments for investigation of their immunobiological functions

Fujimoto, Yukari, Konishi, Yasuko, Kubo, Osamu, Hasegawa, Mizuho, Inohara, Naohiro, Fukase, Koichi

TETRAHEDRON LETTERS 50 （ 26 ） 3631 - 3634 2009年07月

研究論文（学術雑誌）,  ISSN  0040-4039

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Characterization of N-terminal structure of TLR2-activating lipoprotein in Staphylococcus aureus

Kazuki Tawaratsumida; Maiko Furuyashiki; Mami Katsumoto; Yukari Fujimoto; Koichi Fukase; Yasuo Suda; Masahito Hashimoto

Journal of Biological Chemistry 284 （ 14 ） 9147 - 9152 2009年04月

研究論文（学術雑誌）

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Synthesis of diaminopimelic acid containing peptidoglycan fragments and tracheal cytotoxin (TCT) and investigation of their biological functions

Akiko Kawasaki; Yukie Karasudani; Yuji Otsuka; Mizuho Hasegawa; Naohiro Inohara; Yukari Fujimoto; Koichi Fukase

Chemistry - A European Journal 14 （ 33 ） 10318 - 10330 2008年11月

研究論文（学術雑誌）

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Synthesis and Biological Activity of Helicobacter pylori Lipopolysaccharide Partial Structures

Shimoyama, Atsushi, Fujimoto, Yukari, Iwata, Masato, Kasamatsu, Chika, Suda, Yasuo, Kusumoto, Shoichi, Fukase, Koichi

GLYCOBIOLOGY 18 （ 11 ） 1003 - 1003 2008年11月

研究論文（学術雑誌）,  ISSN  0959-6658

Autophagic control of listeria through intracellular innate immune recognition in drosophila

Yano, Tamaki, Mita, Shizuka, Ohmori, Hiroko, Oshima, Yoshiteru, Fujimoto, Yukari, Ueda, Ryu, Takada, Haruhiko, Goldman, William E., Fukase, Koichi, Silverman, Neal, Yoshimori, Tamotsu, Kurata, Shoichiro

NATURE IMMUNOLOGY 9 （ 8 ） 908 - 916 2008年08月

研究論文（学術雑誌）,  ISSN  1529-2908

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Synthesis of Rubrivivax gelatinosus lipid a and analogues for investigation of the structural basis for immunostimulating and inhibitory activities

Fukase, Yoshiyuki, Fujimoto, Yukari, Adachi, Yo, Suda, Yasuo, Kusumoto, Shoichi, Fulkase, Koichi

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN 81 （ 7 ） 796 - 819 2008年07月

研究論文（学術雑誌）,  ISSN  0009-2673

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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

Prasad Rallabhandi; Agnes Awomoyi; Karen E. Thomas; Armelle Phalipon; Yukari Fujimoto; Koichi Fukase; Shoichi Kusumoto; Nilofer Qureshi; Marcelo B. Sztein; Stefanie N. Vogel

Journal of Immunology 180 （ 2 ） 1139 - 1147 2008年01月

研究論文（学術雑誌）

A critical role of RICK/RIP2 polyubiquitination in Nod-induced NF-kappa B activation

Hasegawa, Mizuho, Fujimoto, Yukari, Lucas, Peter C., Nakano, Hiroyasu, Fukase, Koichi, Nunez, Gabriel, Inohara, Naohiro

EMBO JOURNAL 27 （ 2 ） 373 - 383 2008年01月

研究論文（学術雑誌）,  ISSN  0261-4189

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Synthesis of immunoregulatory Helicobacter pylori lipopolysaccharide partial structures

Yukari Fujimoto; Masato Iwata; Noriko Imakita; Atsushi Shimoyama; Yasuo Suda; Shoichi Kusumoto; Koichi Fukase

Tetrahedron Letters 48 （ 37 ） 6577 - 6581 2007年09月

研究論文（学術雑誌）

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ORGN 980-Synthesis of immunostimulating peptidoglycan fragments recognized by intracellular receptor

藤本 ゆかり

ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY 234   113 - 130 2007年08月

研究論文（学術雑誌）,  ISSN  0065-7727

Nod1/RICK and TLR signaling regulate chemokine and antimicrobial innate immune responses in mesothelial cells

Jong-Hwan Park; Yun-Gi Kim; Michael Shaw; Thirumala-Devi Kanneganti; Yukari Fujimoto; Koichi Fukase; Naohiro Inohara; Gabriel Núñez

Journal of Immunology 179 （ 1 ） 514 - 521 2007年07月

研究論文（学術雑誌）

Evidence of immunostimulating lipoprotein existing in the natural lipoteichoic acid fraction

Hashimoto, Masahito, Furuyashiki, Maiko, Kaseya, Ryoko, Fukada, Yuka, Akimaru, Mai, Aoyama, Kazue, Okuno, Toshiomi, Tamura, Toshihide, Kirikae, Teruo, Kirikae, Fumiko, Eiraku, Nobutaka, Morioka, Hirofumi, Fujimoto, Yukari, Fukase, Koichi, Takashige, Katsuhiro, Moriya, Yoichiro, Kusumoto, Shoichi, Suda, Yasuo

INFECTION AND IMMUNITY 75 （ 4 ） 1926 - 1932 2007年04月

研究論文（学術雑誌）,  ISSN  0019-9567

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A role of lipophilic peptidoglycan-related molecules in induction of Nod1-mediated immune responses

Hasegawa, Mizuho, Kawasaki, Akiko, Yang, Kangkang, Fujimoto, Yukari, Masumoto, Junya, Breukink, Eefjan, Nunez, Gabriel, Fukase, Koichi, Inohara, Naohiro

JOURNAL OF BIOLOGICAL CHEMISTRY 282 （ 16 ） 11757 - 11764 2007年04月

研究論文（学術雑誌）,  ISSN  0021-9258

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Inhibition of lipid A-mediated type I interferon induction by Bactericidal/permeability-increasing protein (BPI)

Azuma, Masahiro, Matsuo, Aya, Fujimoto, Yukari, Fukase, Koichi, Hazeki, Kaoru, Hazeki, Osamu, Matsumoto, Misako, Seya, Tsukasa

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS 354 （ 2 ） 574 - 578 2007年03月

研究論文（学術雑誌）,  ISSN  0006-291X

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Chemical synthesis of peptidoglycan fragments for elucidation of the immunostimulating mechanism

Fujimoto, Yukari, Inamura, Seiichi, Kawasaki, Akiko, Shiokawa, Zenyu, Shimoyama, Atsushi, Hashimoto, Takashi, Kusumoto, Shoichi, Fukase, Koichi

JOURNAL OF ENDOTOXIN RESEARCH 13 （ 3 ） 189 - 196 2007年

研究論文（学術雑誌）,  ISSN  0968-0519

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Synthesis of lipid A monosaccharide analogues containing acidic amino acid: Exploring the structural basis for the endotoxic and antagonistic activities

Masao Akamatsu; Yukari Fujimoto; Mikayo Kataoka; Yasuo Suda; Shoichi Kusumoto; Koichi Fukase

Bioorganic and Medicinal Chemistry 14 （ 19 ） 6759 - 6777 2006年10月

研究論文（学術雑誌）

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Differential release and distribution of Nod1 and Nod2 immunostimulatory molecules among bacterial species and environments

Mizuho Hasegawa; Kangkang Yang; Masahito Hashimoto; Jong-Hwan Park; Yun-Gi Kim; Yukari Fujimoto; Gabriel Nuñez; Koichi Fukase; Naohiro Inohara

Journal of Biological Chemistry 281 （ 39 ） 29054 - 29063 2006年09月

研究論文（学術雑誌）

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Sarcoidosis and NOD1 variation with impaired recognition of intracellular Propionibacterium acnes

Tanabe, Tsuyoshi, Ishige, Ikuo, Suzuki, Yoshimi, Aita, Yukie, Furukawa, Asuka, Ishige, Yuki, Uchida, Keisuke, Suzuki, Takashige, Takemura, Tamiko, Ikushima, Soichiro, Oritsu, Masaru, Yokoyama, Tetsuji, Fujimoto, Yukari, Fukase, Koichi, Inohara, Naohiro, Nunez, Gabriel, Eishi, Yoshinobil

BIOCHIMICA ET BIOPHYSICA ACTA-MOLECULAR BASIS OF DISEASE 1762 （ 9 ） 794 - 801 2006年09月

研究論文（学術雑誌）,  ISSN  0925-4439

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Meso-diaminopimelic acid and Meso-lanthionine, amino acids specific to bacterial peptidoglycans, activate human epithelial cells through NOD1

Akiko Uehara; Yukari Fujimoto; Akiko Kawasaki; Shoichi Kusumoto; Koichi Fukase; Haruhiko Takada

Journal of Immunology 177 （ 3 ） 1796 - 1804 2006年08月

研究論文（学術雑誌）

Conformational changes during apoplastocyanin folding observed by photocleavable modification and transient grating

Shun Hirota; Yukari Fujimoto; Jungkwon Choi; Naoki Baden; Noriko Katagiri; Masako Akiyama; Rinske Hulsker; Marcellus Ubbink; Toshihide Okajima; Teruhiro Takabe; Noriaki Funasaki; Yoshihito Watanabe; Masahide Terazima

Journal of the American Chemical Society 128 （ 23 ） 7551 - 7558 2006年06月

研究論文（学術雑誌）

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Toll-like receptors, NOD1, and NOD2 in oral epithelial cells

Y. Sugawara; A. Uehara; Y. Fujimoto; S. Kusumoto; K. Fukase; K. Shibata; S. Sugawara; T. Sasano; H. Takada

Journal of Dental Research 85 （ 6 ） 524 - 529 2006年06月

研究論文（学術雑誌）

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Regulatory roles for MD-2 and TLR4 in ligand-induced receptor clustering

Makiko Kobayashi; Shin-Ichiroh Saitoh; Natsuko Tanimura; Koichiro Takahashi; Kiyoshi Kawasaki; Masahiro Nishijima; Yukari Fujimoto; Koichi Fukase; Sachiko Akashi-Takamura; Kensuke Miyake

Journal of Immunology 176 （ 10 ） 6211 - 6218 2006年05月

研究論文（学術雑誌）

A synthetic peptidoglycan fragment as a competitive inhibitor of the melanization cascade

Won Park Ji; Byung-Rok Je; Shunfu Piao; Seiichi Inamura; Yukari Fujimoto; Koichi Fukase; Shoichi Kusumoto; Kenneth Söderhäll; Nam-Chul Ha; Bok Luel Lee

Journal of Biological Chemistry 281 （ 12 ） 7747 - 7755 2006年03月

研究論文（学術雑誌）

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Nod1 acts as an intracellular receptor to stimulate chemokine production and neutrophil recruitment in vivo

Junya Masumoto; Kangkang Yang; Sooryanarayana Varambally; Mizuho Hasegawa; Scott A. Tomlins; Su Qiu; Yukari Fujimoto; Akiko Kawasaki; Simon J. Foster; Yasuo Horie; Tak W. Mak; Gabriel Núñez; Arul M. Chinnaiyan; Koichi Fukase; Naohiro Inohara

Journal of Cell Biology 172 （ 3 ） 203 - 213 2006年01月

研究論文（学術雑誌）

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Synthesis and bioactivity of fluorescence- and biotin-labeled lipid a analogues for investigation of recognition mechanism in innate immunity

Yukari Fujimoto; Eiji Kimura; Shuichi Murata; Shoichi Kusumoto; Koichi Fukase

Tetrahedron Letters 47 （ 4 ） 539 - 543 2006年01月

研究論文（学術雑誌）

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Synthesis of peptidoglycan fragments and evaluation of their biological activity

Seiichi Inamura; Yukari Fujimoto; Akiko Kawasaki; Zenyu Shiokawa; Eva Woelk; Holger Heine; Buko Lindner; Naohiro Inohara; Shoichi Kusumoto; Koichi Fukase

Organic and Biomolecular Chemistry 4 （ 2 ） 232 - 242 2006年01月

研究論文（学術雑誌）

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Human peptidoglycan recognition protein S is an effector of neutrophil-mediated innate immunity

Hyun Cho Ju; Iain P. Fraser; Koichi Fukase; Shoichi Kusumoto; Yukari Fujimoto; Gregory L. Stahl; R. Alan B. Ezekowitz

Blood 106 （ 7 ） 2551 - 2558 2005年10月

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Highly β-selective mannosylation towards Manβ1-4GlcNAc synthesis: TMSB(C<sub>6</sub>F<sub>5</sub>)<sub>4</sub> as a Lewis acid/cation trap catalyst

Shin-Ichi Tanaka; Mamoru Takashina; Hiroomi Tokimoto; Yukari Fujimoto; Katsunori Tanaka; Koichi Fukase

Synlett  （ 15 ） 2325 - 2328 2005年09月

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Upregulation of PGRPs by chemically synthesized pathogen-associated molecular patterns via Toll-like receptors, NOD1 and NOD2 in oral epithelial cells

Akiko Uehara; Yumiko Sugawara; Shoichiro Kurata; Yukari Fujimoto; Koichi Fukase; Shoichi Kusumoto; Takashi Sasano; Kenichiro Shibata; Shunji Sugawara; Haruhiko Takada

International Congress Series 1284   163 - 168 2005年09月

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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

A. Uehara; Y. Sugawara; S. Kurata; Y. Fujimoto; K. Fukase; S. Kusumoto; Y. Satta; T. Sasano; S. Sugawara; H. Takada

Cellular Microbiology 7 （ 5 ） 675 - 686 2005年05月

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Stereoselective glycosylation using the long-range effect of a [2-(4-phenylbenzyl)oxycarbonyl]benzoyl group

Hiroomi Tokimoto; Yukari Fujimoto; Koichi Fukase; Shoichi Kusumoto

Tetrahedron Asymmetry 16 （ 2 ） 441 - 447 2005年01月

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Synthesis of lipid A and its analogues for investigation of the structural basis for their bioactivity

Yukari Fujimoto; Yo Adachi; Masao Akamatsu; Yoshiyuki Fukase; Mikayo Kataoka; Yasuo Suda; Koichi Fukase; Shoichi Kusumoto

Journal of Endotoxin Research 11 （ 6 ） 341 - 347 2005年01月

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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

A. Uehara; S. Yang; Y. Fujimoto; K. Fukase; S. Kusumoto; K. Shibata; S. Sugawara; H. Takada

Cellular Microbiology 7 （ 1 ） 53 - 61 2005年01月

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Solution and biologically relevant conformations of enantiomeric 11-cis-locked cyclopropyl retinals

Yukari Fujimoto; Nathan Fishkin; Gennaro Pescitelli; John Decatur; Nina Berova; Koji Nakanishi

Journal of the American Chemical Society 124 （ 25 ） 7294 - 7302 2002年06月

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Synthesis of 11-cis-locked bicyclo[5.1.0]octanyl retinal and an enantioselective binding to bovine opsin

Yukari Fujimoto; Rongyuan Xie; Sarah E. Tully; Nina Berova; Koji Nakanishi

Chirality 14 （ 4 ） 340 - 346 2002年01月

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Conformation of the Rhodopsin Chromophore: Studies with Synthetic Chiral Retinoids.

Yukari Fujimoto

Doctoral Thesis (Osaka University) 2002年

学位論文（博士）, 単著

On the bioactive conformation of the rhodopsin chromophore: Absolute sense of twist around the 6-s-cis bond

Yukari Fujimoto; Jun Ishihara; Shojiro Maki; Naoko Fujioka; Tao Wang; Takumi Furuta; Nathan Fishkin; Babak Borhan; Nina Berova; Koji Nakanishi

Chemistry - A European Journal 7 （ 19 ） 4198 - 4204 2001年10月

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Optical Anisotropy of Phenylacetylene Homologues

Chizu Sekine; Koichi Fujisawa; Yukari Fujimoto; Masayoshi Minai

Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals 332   235 - 242 1999年01月

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One step and convenient preparations of 4-hydroxyretinal and 4- oxoretinal

Masaru Hashimoto; Yukari Fujimoto

Synthetic Communications 29 （ 21 ） 3793 - 3797 1999年01月

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Syntheses and physical properties of new biphenyl and phenylpyrimidine type ferroelectric liquid crystals

Takayuki Higashi; Isao Kurimoto; Shoji Toda; Naoyuki Takano; Yukari Fujimoto; Masayoshi Minai; Chizu Sekine; Takeshi Tani; Kayoko Ueda; Koichi Fujisawa

Ferroelectrics 148 （ 1 -4 pt 2 ） 169 - 178 1993年01月

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Physical properties of new phenylpyrimidine type ferroelectric liquid crystals

Chizu Sekine; Takeshi Tani; Kayoko Ueda; Koichi Gujisawa; Takayuki Higashii; Isao Kurimoto; Shoji Toda; Naoyuki Takano; Yukari Fujimoto; Masayoshi Minai

Ferroelectrics 148 （ 1 -4 pt 2 ） 203 - 212 1993年01月

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Physical properties of novel biphenyl and phenylpyrimidine type ferroelectric liquid crystals

Kayoko Ueda; Chizu Sekine; Takeshi Tani; Koichi Fujisawa; Takayuki Higashii; Isao Kurimoto; Shoji Toda; Naoyuki Takano; Yukari Fujimoto; Masayoshi Minai

Ferroelectrics 148 （ 1 -4 pt 2 ） 213 - 222 1993年01月

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Synthesis of allyl 3-deoxy-D-manno-2-octulopyranosidic acid 4- and 5-phosphates

FUJIMOTO YUKARI

Bull. Chem. Soc. Japan    3267 - 3273 1991年

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