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Volumn 6, Issue , 2015, Pages

Total synthesis of tetraacylated phosphatidylinositol hexamannoside and evaluation of its immunomodulatory activity

Author keywords

[No Author keywords available]

Indexed keywords

GAMMA INTERFERON; INTERLEUKIN 4; MANNOSIDE; PHOSPHATIDYLINOSITOL; PHOSPHATIDYLINOSITOL HEXAMANNOSIDE; UNCLASSIFIED DRUG; BACTERIAL PROTEIN; IMMUNOLOGICAL ADJUVANT; OVALBUMIN; STEARIC ACID; STEARIC ACID DERIVATIVE; TETANUS TOXOID; TETRAACYLATED PHOSPHATIDYLINOSITOL HEXAMANNOSIDE; TUBERCULOSTEARIC ACID;

EID: 84930642286     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/ncomms8239     Document Type: Article
Times cited : (27)

References (58)
  • 2
    • 0034972586 scopus 로고    scopus 로고
    • The search for new vaccines against tuberculosis
    • Orme, I. M. The search for new vaccines against tuberculosis. J. Leukoc. Biol. 70, 1-10 (2001
    • (2001) J. Leukoc. Biol , vol.70 , pp. 1-10
    • Orme, I.M.1
  • 3
    • 84896455574 scopus 로고    scopus 로고
    • New antituberculosis drugs, regimens, and adjunct therapies: Needs, advances, and future prospects
    • Zumla, A. I. et al. New antituberculosis drugs, regimens, and adjunct therapies: needs, advances, and future prospects. Lancet Infect. Dis. 14, 327-340 (2014
    • (2014) Lancet Infect. Dis , vol.14 , pp. 327-340
    • Zumla, A.I.1
  • 4
    • 77952326903 scopus 로고    scopus 로고
    • The population dynamics and control of tuberculosis
    • Dye, C. & Williams, B. G. The population dynamics and control of tuberculosis. Science 328, 856-861 (2010
    • (2010) Science , vol.328 , pp. 856-861
    • Dye, C.1    Williams, B.G.2
  • 5
    • 1642431986 scopus 로고    scopus 로고
    • Mycobacterium tuberculosis cell envelope lipids and the host immune response
    • Karakousis, P. C., Bishai, W. R. & Dorman, S. E. Mycobacterium tuberculosis cell envelope lipids and the host immune response. Cell Microbiol. 6, 105-116 (2004
    • (2004) Cell Microbiol , vol.6 , pp. 105-116
    • Karakousis, P.C.1    Bishai, W.R.2    Dorman, S.E.3
  • 6
    • 14644408757 scopus 로고    scopus 로고
    • What's good for the host is good for the bug
    • Flynn, J. L. & Chan, J. What's good for the host is good for the bug. Trends Microbiol. 13, 98-102 (2005
    • (2005) Trends Microbiol , vol.13 , pp. 98-102
    • Flynn, J.L.1    Chan, J.2
  • 7
    • 33845683474 scopus 로고    scopus 로고
    • Who puts the tubercle in tuberculosis?
    • Russell, D. G. Who puts the tubercle in tuberculosis? Nat. Rev. Microbiol. 5, 39-47 (2007
    • (2007) Nat. Rev. Microbiol , vol.5 , pp. 39-47
    • Russell, D.G.1
  • 8
    • 26244436989 scopus 로고    scopus 로고
    • Mycobacterial manipulation of the host cell
    • Hestvik, A. L. K., Hmama, Z. & Av-Gay, Y. Mycobacterial manipulation of the host cell. FEMS Microbiol. Rev. 29, 1041-1050 (2005
    • (2005) FEMS Microbiol. Rev , vol.29 , pp. 1041-1050
    • Hestvik, A.L.K.1    Hmama, Z.2    Av-Gay, Y.3
  • 10
    • 53149117862 scopus 로고    scopus 로고
    • How Mycobacterium tuberculosis subverts host immune responses
    • Józefowski, S., Sobota, A. & Kwiatkowska, K. How Mycobacterium tuberculosis subverts host immune responses. BioEssays 30, 943-954 (2008
    • (2008) BioEssays , vol.30 , pp. 943-954
    • Józefowski, S.1    Sobota, A.2    Kwiatkowska, K.3
  • 11
    • 77953044679 scopus 로고    scopus 로고
    • Chemical approaches for the study of the mycobacterial glycolipids phosphatidylinositol mannosides, lipomannan and lipoarabinomannan
    • Cao, B. & Williams, S. J. Chemical approaches for the study of the mycobacterial glycolipids phosphatidylinositol mannosides, lipomannan and lipoarabinomannan. Nat. Prod. Rep. 27, 919-947 (2010
    • (2010) Nat. Prod. Rep , vol.27 , pp. 919-947
    • Cao, B.1    Williams, S.J.2
  • 12
    • 0035860824 scopus 로고    scopus 로고
    • Acylation state of the phosphatidylinositol mannosides from Mycobacterium bovis Bacillus Calmette Gue'rin and ability to induce granuloma and recruit natural killer T cells
    • Gilleron, M. et al. Acylation state of the phosphatidylinositol mannosides from Mycobacterium bovis Bacillus Calmette Gue'rin and ability to induce granuloma and recruit natural killer T cells. J. Biol. Chem. 276, 34896-34904 (2001
    • (2001) J. Biol. Chem , vol.276 , pp. 34896-34904
    • Gilleron, M.1
  • 13
    • 33746190791 scopus 로고    scopus 로고
    • Fine discrimination in the recognition of individual species of phosphatidyl-myo-inositol mannosides from Mycobacterium tuberculosis by C-type lectin pattern recognition receptors
    • Torrelles, J. B., Azad, A. K. & Schlesinger, L. S. Fine discrimination in the recognition of individual species of phosphatidyl-myo-inositol mannosides from Mycobacterium tuberculosis by C-type lectin pattern recognition receptors. J. Immunol. 177, 1805-1816 (2006
    • (2006) J. Immunol , vol.177 , pp. 1805-1816
    • Torrelles, J.B.1    Azad, A.K.2    Schlesinger, L.S.3
  • 14
    • 3242709268 scopus 로고    scopus 로고
    • Mycobacterial phosphatidylinositol mannoside is a natural antigen for CD1d-restricted T cells
    • Fischer, K. et al. Mycobacterial phosphatidylinositol mannoside is a natural antigen for CD1d-restricted T cells. Proc. Natl Acad. Sci. USA 101, 10685-10690 (2004
    • (2004) Proc. Natl Acad. Sci. USA , vol.101 , pp. 10685-10690
    • Fischer, K.1
  • 15
    • 33747798345 scopus 로고    scopus 로고
    • Phosphatidylinositol mannoside from Mycobacterium tuberculosis binds a5b1 integrin (VLA-5) on CD4 T cells and induces adhesion to fibronectin
    • Rojas, R. E. et al. Phosphatidylinositol mannoside from Mycobacterium tuberculosis binds a5b1 integrin (VLA-5) on CD4 T cells and induces adhesion to fibronectin. J. Immunol. 177, 2959-2968 (2006
    • (2006) J. Immunol , vol.177 , pp. 2959-2968
    • Rojas, R.E.1
  • 16
    • 77958535834 scopus 로고    scopus 로고
    • Molecular basis of phosphatidyl-myo-inositol mannoside biosynthesis and regulation in mycobacteria
    • Guerin, M. E., Korduláková, J., Alzari, P. M., Brennan, P. J. & Jackson, M. Molecular basis of phosphatidyl-myo-inositol mannoside biosynthesis and regulation in mycobacteria. J. Biol. Chem. 285, 33577-33583 (2010
    • (2010) J. Biol. Chem , vol.285 , pp. 33577-33583
    • Guerin, M.E.1    Korduláková, J.2    Alzari, P.M.3    Brennan, P.J.4    Jackson, M.5
  • 17
    • 0007484081 scopus 로고
    • Iodinium ion-mediated mannosylations of myo-inositol: Synthesis of a mycobacteria phospholipid fragment
    • Elie, C. J. J., Verduyn, R., Dreef, C. E., van der Marel, G. A. & van Boom, J. H. Iodinium ion-mediated mannosylations of myo-inositol: synthesis of a mycobacteria phospholipid fragment. J. Carbohydr. Chem. 11, 715-739 (1992
    • (1992) J. Carbohydr. Chem , vol.11 , pp. 715-739
    • Elie, C.J.J.1    Verduyn, R.2    Dreef, C.E.3    Van Der Marel, G.A.4    Van Boom, J.H.5
  • 18
    • 0031012215 scopus 로고    scopus 로고
    • Synthesis of 2 6-di-O-A-Dmannopyranosylphosphatidyl-D-myo-inositol Utilization of glycosylation and phosphorylation based on phosphite chemistry
    • Watanabe, Y., Yamamoto, T. & Okazaki, T. Synthesis of 2, 6-di-O-A-Dmannopyranosylphosphatidyl-D-myo-inositol. Utilization of glycosylation and phosphorylation based on phosphite chemistry. Tetrahedron 53, 903-918 (1997
    • (1997) Tetrahedron , vol.53 , pp. 903-918
    • Watanabe, Y.1    Yamamoto, T.2    Okazaki, T.3
  • 19
    • 0345528938 scopus 로고    scopus 로고
    • Synthesis of phosphatidylinositol mannosides (PIMs
    • Stadelmaier, A. & Schmidt, R. R. Synthesis of phosphatidylinositol mannosides (PIMs). Carbohydr. Res. 338, 2557-2569 (2003
    • (2003) Carbohydr. Res , vol.338 , pp. 2557-2569
    • Stadelmaier, A.1    Schmidt, R.R.2
  • 20
    • 4544237422 scopus 로고    scopus 로고
    • Synthesis of serine-linked phosphatidylinositol mannosides (PIMs
    • Stadelmaier, A., Biskup, M. B. & Schmidt, R. R. Synthesis of serine-linked phosphatidylinositol mannosides (PIMs). Eur. J. Org. Chem. 2004, 3292-3303 (2004
    • (2004) Eur. J. Org. Chem , vol.2004 , pp. 3292-3303
    • Stadelmaier, A.1    Biskup, M.B.2    Schmidt, R.R.3
  • 21
    • 2942562479 scopus 로고    scopus 로고
    • Synthesis of a key Mycobacterium tuberculosis biosynthetic phosphoinositide intermediate
    • Jayaprakash, K. N., Lu, J. & Fraser-Reid, B. Synthesis of a key Mycobacterium tuberculosis biosynthetic phosphoinositide intermediate. Bioorg. Med. Chem. Lett. 14, 3815-3819 (2004
    • (2004) Bioorg. Med. Chem. Lett , vol.14 , pp. 3815-3819
    • Jayaprakash, K.N.1    Lu, J.2    Fraser-Reid, B.3
  • 22
    • 24944510431 scopus 로고    scopus 로고
    • Synthesis of a lipomannan component of the cell-wall complex of Mycobacterium tuberculosis is based on Paulsen's concept of donor/acceptor ''match
    • Jayaprakash, K. N., Lu, J. & Fraser-Reid, B. Synthesis of a lipomannan component of the cell-wall complex of Mycobacterium tuberculosis is based on Paulsen's concept of donor/acceptor ''match. Angew. Chem. Int. Ed. 44, 5894-5898 (2005
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 5894-5898
    • Jayaprakash, K.N.1    Lu, J.2    Fraser-Reid, B.3
  • 23
    • 33745616513 scopus 로고    scopus 로고
    • Phosphatidylinositol mannosides: Synthesis and suppression of allergic airway disease
    • Ainge, G. D. et al. Phosphatidylinositol mannosides: synthesis and suppression of allergic airway disease. Bioorg. Med. Chem. 14, 5632-5642 (2006
    • (2006) Bioorg. Med. Chem , vol.14 , pp. 5632-5642
    • Ainge, G.D.1
  • 24
    • 33749258201 scopus 로고    scopus 로고
    • Phosphatidylinositol mannosides: Synthesis and adjuvant properties of phosphatidylinositol di-And tetramannosides
    • Ainge, G. D. et al. Phosphatidylinositol mannosides: synthesis and adjuvant properties of phosphatidylinositol di-And tetramannosides. Bioorg. Med. Chem. 14, 7615-7624 (2006
    • (2006) Bioorg. Med. Chem , vol.14 , pp. 7615-7624
    • Ainge, G.D.1
  • 25
    • 33645418472 scopus 로고    scopus 로고
    • Total synthesis of phosphatidylinositol mannosides of Mycobacterium tuberculosis
    • Liu, X., Stocker, B. L. & Seeberger, P. H. Total synthesis of phosphatidylinositol mannosides of Mycobacterium tuberculosis. J. Am. Chem. Soc. 128, 3638-3648 (2006
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 3638-3648
    • Liu, X.1    Stocker, B.L.2    Seeberger, P.H.3
  • 26
    • 34247634467 scopus 로고    scopus 로고
    • Synthesis and structure of phosphatidylinositol dimannoside
    • Dyer, B. S. et al. Synthesis and structure of phosphatidylinositol dimannoside. J. Org. Chem. 72, 3282-3288 (2007
    • (2007) J. Org. Chem , vol.72 , pp. 3282-3288
    • Dyer, B.S.1
  • 27
    • 34447304618 scopus 로고    scopus 로고
    • Phosphatidylinositol mannoside ether analogues: Syntheses and interleukin-12-inducing properties
    • Ainge, G. D. et al. Phosphatidylinositol mannoside ether analogues: syntheses and interleukin-12-inducing properties. J. Org. Chem. 72, 5291-5296 (2007
    • (2007) J. Org. Chem , vol.72 , pp. 5291-5296
    • Ainge, G.D.1
  • 28
    • 57549098955 scopus 로고    scopus 로고
    • Chemical synthesis of all phosphatidylinositol mannoside (PIM) glycans from Mycobacterium tuberculosis
    • Boonyarattanakalin, S., Liu, X., Michieletti, M., Lepenies, B. & Seeberger, P. H. Chemical synthesis of all phosphatidylinositol mannoside (PIM) glycans from Mycobacterium tuberculosis. J. Am. Chem. Soc. 130, 16791-16799 (2008
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 16791-16799
    • Boonyarattanakalin, S.1    Liu, X.2    Michieletti, M.3    Lepenies, B.4    Seeberger, P.H.5
  • 29
    • 68949175683 scopus 로고    scopus 로고
    • Total synthesis of a fully lipidated form of phosphatidyl-myo-inositol dimannoside (PIM-2) of Mycobacterium tuberculosis
    • Ali, A., Wenk, M. R. & Lear, M. J. Total synthesis of a fully lipidated form of phosphatidyl-myo-inositol dimannoside (PIM-2) of Mycobacterium tuberculosis. Tetrahedron Lett. 50, 5664-5666 (2009
    • (2009) Tetrahedron Lett , vol.50 , pp. 5664-5666
    • Ali, A.1    Wenk, M.R.2    Lear, M.J.3
  • 30
    • 58449137104 scopus 로고    scopus 로고
    • Total synthesis of phosphatidylinositol dimannoside: A cell-envelope component of Mycobacterium tuberculosis
    • Patil, P. S. & Hung, S.-C. Total synthesis of phosphatidylinositol dimannoside: a cell-envelope component of Mycobacterium tuberculosis. Chem. Eur. J. 15, 1091-1094 (2009
    • (2009) Chem. Eur. J. , vol.15 , pp. 1091-1094
    • Patil, P.S.1    Hung, S.-C.2
  • 31
    • 77952997466 scopus 로고    scopus 로고
    • Synthesis of mycobacterial triacylated phosphatidylinositol dimannoside containing an acyl lipid chain at 3-O of inositol
    • Patil, P. S. & Hung, S.-C. Synthesis of mycobacterial triacylated phosphatidylinositol dimannoside containing an acyl lipid chain at 3-O of inositol. Org. Lett. 12, 2618-2621 (2010
    • (2010) Org. Lett , vol.12 , pp. 2618-2621
    • Patil, P.S.1    Hung, S.-C.2
  • 32
    • 79958837488 scopus 로고    scopus 로고
    • Chemical synthesis and immunosuppressive activity of dipalmitoyl phosphatidylinositol hexamannoside
    • Ainge, G. D. et al. Chemical synthesis and immunosuppressive activity of dipalmitoyl phosphatidylinositol hexamannoside. J. Org. Chem. 76, 4941-4951 (2011
    • (2011) J. Org. Chem , vol.76 , pp. 4941-4951
    • Ainge, G.D.1
  • 33
    • 80054927544 scopus 로고    scopus 로고
    • Synthesis and Toll-like receptor 4 (TLR4) activity of phosphatidylinositol dimannoside analogues
    • Ainge, G. D. et al. Synthesis and Toll-like receptor 4 (TLR4) activity of phosphatidylinositol dimannoside analogues. J. Med. Chem. 54, 7268-7279 (2011
    • (2011) J. Med. Chem , vol.54 , pp. 7268-7279
    • Ainge, G.D.1
  • 34
    • 84865208298 scopus 로고    scopus 로고
    • Synthesis and mass spectral characterization of mycobacterial phosphatidylinositol and its dimannosides
    • Rankin, G. M. et al. Synthesis and mass spectral characterization of mycobacterial phosphatidylinositol and its dimannosides. J. Org. Chem. 77, 6743-6759 (2012
    • (2012) J. Org. Chem , vol.77 , pp. 6743-6759
    • Rankin, G.M.1
  • 35
    • 0345134721 scopus 로고    scopus 로고
    • Regioselective protection and deprotection of inositol hydroxyl groups
    • Sureshan, K. M., Shashidhar, M. S., Praveen, T. & Das, T. Regioselective protection and deprotection of inositol hydroxyl groups. Chem. Rev. 103, 4477-4504 (2003
    • (2003) Chem. Rev , vol.103 , pp. 4477-4504
    • Sureshan, K.M.1    Shashidhar, M.S.2    Praveen, T.3    Das, T.4
  • 37
    • 0035917329 scopus 로고    scopus 로고
    • Novel synthesis of enantiomerically pure natural inositols and their diastereoisomers
    • Takahashi, H., Kittaka, H. & Ikegami, S. Novel synthesis of enantiomerically pure natural inositols and their diastereoisomers. J. Org. Chem. 66, 2705-2716 (2001
    • (2001) J. Org. Chem , vol.66 , pp. 2705-2716
    • Takahashi, H.1    Kittaka, H.2    Ikegami, S.3
  • 39
    • 34247474417 scopus 로고    scopus 로고
    • Regioselective one-pot protection of carbohydrates
    • Wang, C.-C. et al. Regioselective one-pot protection of carbohydrates. Nature 446, 896-899 (2007
    • (2007) Nature , vol.446 , pp. 896-899
    • Wang, C.-C.1
  • 42
    • 79952578941 scopus 로고    scopus 로고
    • One-pot strategies for the synthesis of the tetrasaccharide linkage region of proteoglycans
    • Huang, T.-Y., Zulueta, M. M. L. & Hung, S.-C. One-pot strategies for the synthesis of the tetrasaccharide linkage region of proteoglycans. Org. Lett. 13, 1506-1509 (2011
    • (2011) Org. Lett , vol.13 , pp. 1506-1509
    • Huang, T.-Y.1    Zulueta, M.M.L.2    Hung, S.-C.3
  • 43
    • 84876959359 scopus 로고    scopus 로고
    • Regioselective and stereoselective benzylidene installation and one-pot protection of D-mannose
    • Patil, P. S., Lee, C.-C., Huang, Y.-W., Zulueta, M. M. L. & Hung, S.-C. Regioselective and stereoselective benzylidene installation and one-pot protection of D-mannose. Org. Biomol. Chem. 11, 2605-2612 (2013
    • (2013) Org. Biomol. Chem , vol.11 , pp. 2605-2612
    • Patil, P.S.1    Lee, C.-C.2    Huang, Y.-W.3    Zulueta, M.M.L.4    Hung, S.-C.5
  • 44
    • 84889877353 scopus 로고    scopus 로고
    • Regioselective one-pot protection, protection-glycosylation and protection-glycosylation-glycosylation of carbohydrates: A case study with D-glucose
    • Huang, T.-Y., Zulueta, M. M. L. & Hung, S.-C. Regioselective one-pot protection, protection-glycosylation and protection-glycosylation-glycosylation of carbohydrates: a case study with D-glucose. Org. Biomol. Chem. 12, 376-382 (2014
    • (2014) Org. Biomol. Chem , vol.12 , pp. 376-382
    • Huang, T.-Y.1    Zulueta, M.M.L.2    Hung, S.-C.3
  • 45
    • 17044368829 scopus 로고    scopus 로고
    • Cu(OTf)2 as an efficient and dual-purpose catalyst in the regioselective reductive ring opening of benzylidene acetals
    • Shie, C.-R. et al. Cu(OTf)2 as an efficient and dual-purpose catalyst in the regioselective reductive ring opening of benzylidene acetals. Angew. Chem. Int. Ed. 44, 1665-1668 (2005
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 1665-1668
    • Shie, C.-R.1
  • 46
    • 0037007836 scopus 로고    scopus 로고
    • Synthesis of biologically potent a1-2-linked disaccharide derivatives via regioselective one-pot protection-glycosylation
    • Wang, C.-C. et al. Synthesis of biologically potent a1-2-linked disaccharide derivatives via regioselective one-pot protection-glycosylation. Angew. Chem. Int. Ed. 41, 2360-2362 (2002
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 2360-2362
    • Wang, C.-C.1
  • 47
    • 4244144203 scopus 로고
    • A study of 13CH coupling constants in hexopyranoses
    • Bock, K. & Pedersen, C. A study of 13CH coupling constants in hexopyranoses. J. Chem. Soc. Perkin. Trans. 2, 293-297 (1974
    • (1974) J. Chem. Soc. Perkin. Trans , vol.2 , pp. 293-297
    • Bock, K.1    Pedersen, C.2
  • 48
    • 0034508404 scopus 로고    scopus 로고
    • Carbohydrate structural determination by NMR spectroscopy: Modern methods and limitations
    • Duus, J. Gotfredsen, C. H. & Bock, K. Carbohydrate structural determination by NMR spectroscopy: modern methods and limitations. Chem. Rev. 100, 4589-4614 (2000
    • (2000) Chem. Rev , Issue.100 , pp. 4589-4614
    • Duus J.Ø.1    Gotfredsen, C.H.2    Bock, K.3
  • 49
    • 84861606047 scopus 로고    scopus 로고
    • A-Glycosylation by D-glucosamine-derived donors: Synthesis of heparosan and heparin analogues that interact with mycobacterial heparin-binding hemagglutinin
    • Zulueta, M. M. L. et al. a-Glycosylation by D-glucosamine-derived donors: synthesis of heparosan and heparin analogues that interact with mycobacterial heparin-binding hemagglutinin. J. Am. Chem. Soc. 134, 8988-8995 (2012
    • (2012) J. Am. Chem. Soc , vol.134 , pp. 8988-8995
    • Zulueta, M.M.L.1
  • 50
    • 0023213863 scopus 로고
    • Diagnosis of tuberculous meningitis by detection of tuberculostearic acid in cerebrospinal fluid
    • French, G. L. et al. Diagnosis of tuberculous meningitis by detection of tuberculostearic acid in cerebrospinal fluid. Lancet 330, 117-119 (1987
    • (1987) Lancet , vol.330 , pp. 117-119
    • French, G.L.1
  • 51
  • 52
    • 33645421015 scopus 로고
    • A new synthesis of tuberculostearic acid
    • Schmidt, G. A. & Shirley, D. A. A new synthesis of tuberculostearic acid. J. Am. Chem. Soc. 71, 3804-3806 (1949
    • (1949) J. Am. Chem. Soc , vol.71 , pp. 3804-3806
    • Schmidt, G.A.1    Shirley, D.A.2
  • 53
    • 33646766796 scopus 로고    scopus 로고
    • A new short synthesis of 10-(R)-tuberculostearic acid and its enantiomer
    • Roberts, I. O. & Baird, M. S. A new short synthesis of 10-(R)-tuberculostearic acid and its enantiomer. Chem. Phys. Lipids 142, 111-117 (2006
    • (2006) Chem. Phys. Lipids , vol.142 , pp. 111-117
    • Roberts, I.O.1    Baird, M.S.2
  • 54
    • 77957579651 scopus 로고    scopus 로고
    • A concise total synthesis of amphidinolide T2
    • Li, H., Wu, J., Luo, J. & Dai, W.-M. A concise total synthesis of amphidinolide T2. Chem. Eur. J. 16, 11530-11534 (2010
    • (2010) Chem. Eur. J. , vol.16 , pp. 11530-11534
    • Li, H.1    Wu, J.2    Luo, J.3    Dai, W.-M.4
  • 55
    • 79959998176 scopus 로고    scopus 로고
    • Expeditious oligosaccharide synthesis via selective, semi-orthogonal, and orthogonal activation
    • Kaeothip, S. & Demchenko, A. V. Expeditious oligosaccharide synthesis via selective, semi-orthogonal, and orthogonal activation. Carbohydr. Res. 346, 1371-1388 (2011
    • (2011) Carbohydr. Res , vol.346 , pp. 1371-1388
    • Kaeothip, S.1    Demchenko, A.V.2
  • 56
    • 84905397678 scopus 로고    scopus 로고
    • The T-Cell response to lipid antigens of Mycobacterium tuberculosis
    • De Libero, G. & Mori, L. The T-Cell response to lipid antigens of Mycobacterium tuberculosis. Front. Immunol. 5, 219 (2014
    • (2014) Front. Immunol , vol.5 , Issue.219
    • De Libero, G.1    Mori, L.2
  • 57
    • 84892374260 scopus 로고    scopus 로고
    • Synthesis of RCAI-172 (C6 epimer of RCAI-147) and its biological activity
    • Shiozaki, M. et al. Synthesis of RCAI-172 (C6 epimer of RCAI-147) and its biological activity. Bioorg. Med. Chem. 22, 827-833 (2014
    • (2014) Bioorg. Med. Chem , vol.22 , pp. 827-833
    • Shiozaki, M.1
  • 58
    • 0028186224 scopus 로고
    • Anomeric-oxygen activation for glycoside syn
    • thesis: the trichloroacetimidate method
    • Schmidt, R. R. & Kinzy, W. Anomeric-oxygen activation for glycoside synthesis: the trichloroacetimidate method. Adv. Carbohydr. Chem. Biochem. 50, 21-123 (1994
    • (1994) Adv. Carbohydr. Chem. Biochem , vol.50 , pp. 21-123
    • Schmidt, R.R.1    Kinzy, W.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.