Studies on biological function of glycoconjugates using synthetic probes and in vivo imaging
Project/Area Number |
23241074
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Research Category |
Grant-in-Aid for Scientific Research (A)
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Allocation Type | Single-year Grants |
Section | 一般 |
Research Field |
Chemical biology
|
Research Institution | Osaka University |
Principal Investigator |
FUKASE Koichi 大阪大学, 理学(系)研究科(研究院), 教授 (80192722)
|
Co-Investigator(Kenkyū-buntansha) |
TANAKA Katsunori 大阪大学, 大学院理学研究科, 助教 (00403098)
MANABE Yoshiyuki 大阪大学, 大学院理学研究科, 助教 (00632093)
|
Project Period (FY) |
2011-04-01 – 2015-03-31
|
Project Status |
Completed (Fiscal Year 2014)
|
Budget Amount *help |
¥49,400,000 (Direct Cost: ¥38,000,000、Indirect Cost: ¥11,400,000)
Fiscal Year 2013: ¥14,170,000 (Direct Cost: ¥10,900,000、Indirect Cost: ¥3,270,000)
Fiscal Year 2012: ¥14,170,000 (Direct Cost: ¥10,900,000、Indirect Cost: ¥3,270,000)
Fiscal Year 2011: ¥21,060,000 (Direct Cost: ¥16,200,000、Indirect Cost: ¥4,860,000)
|
Keywords | 自然免疫リガンド / リピドA / ペプチドグリカン / N-グリカン / イメージング / 糖鎖合成 / Nod1、Nod2 / ヘリコバクター・ピロリ菌 / 自然免疫 / 癌マーカー / リポ多糖 |
Outline of Final Research Achievements |
We have developed novel synthetic methods for the effective synthesis of glycoconjugates and achieved the synthesis and biological assay of various types of glycans and glycoconjugates. Some immunomodulating glycoconjugates were revealed as a prospective candidate for an immune adjuvant. We also synthesize N-glycans which have core fucose and bisecting GlcNAc to investigate its function. In vivo imaging of various kinds of N-glycans clearly showed that the structure of N-glycans have influence on their dynamics.
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Report
(4 results)
Research Products
(177 results)
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[Journal Article] Molecular basis for bacterial peptidoglycan recognition by LysM domains.2014
Author(s)
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.
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Journal Title
Nat. Commun.
Volume: 5
Issue: 1
Pages: 4269-4269
DOI
Related Report
Peer Reviewed / Open Access
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[Journal Article] Revisiting the bromination of C-H bonds with molecular bromine by using a photo-microflow system.2014
Author(s)
Manabe, Y., Kitawaki, Y., Nagasaki, M., Fukase, K., Matsubara, H., Hino, Y., Fukuyama, T., Ryu, I.
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Journal Title
Chem. Eur. J.
Volume: 20
Issue: 40
Pages: 12750-12753
DOI
Related Report
Peer Reviewed / Open Access / Acknowledgement Compliant
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[Journal Article] Efficient Glycosylation Using In(OTf)<sub>3</sub> as a Lewis Acid: Activation of <i>N</i>-Phenyltrifluoroacetimidate or Thioglycosides with Halogenated Reagents or PhIO2014
Author(s)
Salmasan, R. M., Manabe, Y., Kitawaki, Y., Chang, T.-C., Fukase, K.
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Journal Title
Chemistry Letters
Volume: 43
Issue: 6
Pages: 956-958
DOI
NAID
ISSN
0366-7022, 1348-0715
Related Report
Peer Reviewed / Acknowledgement Compliant
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[Journal Article] Bacterial lipopeptides as toll-like receptor 2 (TLR2) ligands; synthesis, function and its application.2014
Author(s)
Fujimoto, Y., Kajiki, Y., Kawahara, Y, Katsumoto, M., Fukase, K.
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Journal Title
Peptide Science
Volume: 2013
Pages: 41-42
Related Report
Peer Reviewed
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[Journal Article] One-pot synthesis of N-acetyl- and N-glycolylneuraminic Acid capped trisaccharides and evaluation of their influenza a(h1 n1) inhibition.2014
Author(s)
Hsu, Y., Ma, HH., Lico, LS., Jan, JT., Fukase, K., Uchinashi, Y., Zulueta, MM., Hung, SC.
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Journal Title
Angew Chem Int Ed
Volume: 53
Issue: 9
Pages: 2413-2416
DOI
Related Report
Peer Reviewed
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[Journal Article] A cascading reaction sequence involving ligand-directed azaelectrocyclization and autooxidation-induced fluorescence recovery enables visualization of target proteins on the surfaces of live cells.2014
Author(s)
Tanaka, K., Kitadani, M., Tsutsui, A., Pradipta, AR., Imamaki, R., Kitazume, S., Taniguchi, N., Fukase K.
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Journal Title
Org Biomol Chem.
Volume: 12
Issue: 9
Pages: 1412-1418
DOI
Related Report
Peer Reviewed
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[Journal Article] Development of bis-unsaturated ester aldehydes as amino-glue probes: sequential double azaelectrocyclization as a promising strategy for bioconjugation.2013
Author(s)
Tanaka, K., Nakamoto, Y., Siwu, ER., Pradipta, AR., Morimoto, K., Fujiwara, T., Yoshida, S., Hosoya, T., Tamura, Y., Hirai, G., Sodeoka, M., Fukase, K.
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Journal Title
Org Biomol Chem.,
Volume: 11
Issue: 42
Pages: 7326-7333
DOI
Related Report
Peer Reviewed / Acknowledgement Compliant
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[Journal Article] Whole-body imaging of tumor cells by azaelectrocyclization: Visualization of metastasis dependence on glycan structure2013
Author(s)
Tanaka, K., Moriwaki, K., Yokoi, S., Koyama, K., Miyoshi, E., Fukase, K.
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Journal Title
Bioorg. Med. Chem.
Volume: 21(5)
Issue: 5
Pages: 614-621
DOI
Related Report
Peer Reviewed
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[Journal Article] Innate immunomodulation by lipophilic termini of lipopolysaccharide; synthesis of lipid A from Porphyromonas gingivalis and other bacteria and their immunomodulative response2013
Author(s)
Fujimoto, Y., Shimoyama, A., Saeki, A., Kitayama, N., Kasamatsu, C., Tsutsui, H., Fukase, K.
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Journal Title
Mol. BioSyst.
Volume: 9
Issue: 5
Pages: 987-996
DOI
Related Report
Peer Reviewed
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[Journal Article] Peptidoglycan as innate immunomodulator; chemical synthesis of its fragments, immunostimulatory activities, and natural Nod1 ligand structures in the environments/fermented food2013
Author(s)
Fujimoto, Y., Pradipta, R. A., Hashimoto, M., Kan, S., Shigehisa, H., Fukase, K.
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Journal Title
Peptide Science
Volume: 2012
Pages: 97-98
NAID
Related Report
Peer Reviewed
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[Journal Article] Structural characterization of neutral and acidic glycolipids from Thermus thermophilus HB82012
Author(s)
Suda, Y., Okazaki, F., Hasegawa, Y., Adachi, S., Fukase, K., Kokubo, S., Kuramitsu, S., Kusumoto, S.
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Journal Title
PLoS One
Volume: 7(7)
Issue: 7
Pages: e35067-e35067
DOI
Related Report
Peer Reviewed
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[Journal Article] Cell surface biotinylation by azaelectrocyclization: Easy-handling and versatile approach for living cell labeling.2012
Author(s)
Tanaka,K., Yokoi, S., Morimoto, K., Iwata, T., Nakamoto, Y., Nakayama, K., Koyama, K., Fujiwara, T., Fukase, K.
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Journal Title
Bioorg. Med. Chem.
Volume: 20
Issue: 6
Pages: 1865-1868
DOI
Related Report
Peer Reviewed
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[Journal Article] Structural and mechanistic analysis of the membrane-embedded glycosyltransferase WaaA required for lipopolysaccharide synthesis2012
Author(s)
Schmidt, H., Hansen, G., Singh, S., Hanuszkiewicz, A., Lindner, B., Fukase, K., Woodard, W.R., Holst, O., Hilgenfeld, R., Mamat, U., Mesters, R. J.
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Journal Title
Proc. Natl. Acad. Sci. USA
Volume: 109 (16)
Issue: 16
Pages: 6253-6258
DOI
Related Report
Peer Reviewed
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[Journal Article] Auxiliary-directed oxidation of ursolic acid by 'Ru'-porphyrins : chemical modulation of cytotoxicity against tumor cell lines2012
Author(s)
Tanaka, K., Mazumder, K., Siwu, E.R.O., Nozaki, Satoshi, Watanabe, Y., Fukase, K.
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Journal Title
Tetrahedron Lett.
Volume: 53
Issue: 14
Pages: 1756-1759
DOI
Related Report
Peer Reviewed
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[Journal Article] Template-assisted and self-activating clicked peptide as a synthetic mimic of SH2 domain2011
Author(s)
Tanaka, K., Shirotsuki, S., Kageyama, C., Tahara, T., Nozaki, S., Siwu, E.R.O., Iwata, T., Tamura, S., Douke, S., Murakami, N., Onoe, H., Watanabe, Y., Fukase, K
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Journal Title
ACS Chem.Biol.
Volume: (未定)(in press)
Issue: 4
Pages: 637-645
DOI
Related Report
Peer Reviewed
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[Journal Article] Chemical synthesis of Helicobacter pylori lipopolysaccharide partial structures and their selective proinflammatory response2011
Author(s)
Shimoyama, A., Saeki, A., Tanimura, N., Tsutsui, H., Miyake, K., Suda, Y., Fujimoto, Y., Fukase, K.
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Journal Title
Chem.--Eur.J.
Volume: 17
Issue: 51
Pages: 14464-14474
DOI
Related Report
Peer Reviewed
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[Journal Article] Failure of mycoplasma lipoprotein MALP-2 to induce NK cell activation through dendritic cell TLR22011
Author(s)
Sawahata, R., Shime, H., Yamazaki, S., Inoue, N., Akazawa, T., Fujimoto, Y., Fukase, K., Matsumoto, M. and Seya, T.
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Journal Title
Microbes and Infection
Volume: 13
Issue: 4
Pages: 350-358
DOI
NAID
Related Report
Peer Reviewed
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[Presentation] Synthesis of Inositol Phospholipids as an NKT Cell Modulator)2014
Author(s)
Toshihiko Aiba, Masaki Sato, Daichi Umegaki, Shou Nakagawa, Shinji Tanaka, Masato Kitamura, Shinsuke Inuki, Koichi Fukase, Yukari Fujimoto
Organizer
Joint Meeting of the Society for Glycobiology (SFG) and the Japanese Society of Carbohydrate Research (JSCR) (SFG-JSCR 2014)
Place of Presentation
Honolulu(USA)
Year and Date
2014-11-16 – 2014-11-19
Related Report
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[Presentation] Modulation of Immune Responses via TLR4/MD-2 with Synthetic Isoprenoids2014
Author(s)
Keisuke Mizote, Akinori Saeki, Hiroe Honda, Naoki Okamoto, Takahito Kimura, Yoshinori Nagai, Kiyoshi Takatsu, Yukari Fujimoto, Koichi Fukase
Organizer
Joint Meeting of the Society for Glycobiology (SFG) and the Japanese Society of Carbohydrate Research (JSCR) (SFG-JSCR 2014)
Place of Presentation
Honolulu(USA)
Year and Date
2014-11-16 – 2014-11-19
Related Report
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[Presentation] An Efficient Synthesis of α-Gal epitope2014
Author(s)
Kento Tokunaga, Yoshiyuki Manabe and Koichi Fukase
Organizer
The Ninth International Symposium on Integrated Synthesis(ISIS9)
Place of Presentation
Awaji Yumebutai International Conference Center (Hyogo)
Year and Date
2014-11-14 – 2014-11-15
Related Report
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[Presentation] Library-oriented Synthetic Study of N-Glycans2012
Author(s)
Yoshiyuki Manabe, Masahiro Nagasaki, Naoya Minamoto, Regina Salmasan, Katsunori Tanaka, Koichi Fukase
Organizer
The 7th international conference on cutting-edge organic chemistry in Asia / The 3rd new phase international conference on cutting-edge organic chemistry (ICCEOCA-7 / NICCEOCA-3)
Place of Presentation
Nanyang Technological University (Singapore)
Related Report
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[Presentation] Library Oriented Synthetic Study of N-Glycans2012
Author(s)
Yoshiyuki Manabe, Masahiro Nagasaki, Naoya Minamoto, Regina Salmasan, Katsunori Tanaka, Koichi Fukase
Organizer
The Twelfth International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-12)
Place of Presentation
Rihga Royal Hotel Kyoto
Related Report
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[Book] 未来材料2012
Author(s)
藤本ゆかり
Total Pages
70
Publisher
エヌ・ティー・エス
Related Report
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[Book] 実験医学2012
Author(s)
深瀬浩一、田中克典
Total Pages
225
Publisher
羊土社
Related Report
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