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Article Navigation >  Journal of Pharmaceutical Practice and Service  > 2015  >  33(6): 481-485,569

HUANG Lei, XU Kehan, WU Junqi, YAO Kuo, YU Shichong, WU Qiuye. Research progress in the synthesis of antigen Bacillus anthracis tetrasaccharide[J]. Journal of Pharmaceutical Practice and Service, 2015, 33(6): 481-485,569. doi: 10.3969/j.issn.1006-0111.2015.06.001
Citation: HUANG Lei, XU Kehan, WU Junqi, YAO Kuo, YU Shichong, WU Qiuye. Research progress in the synthesis of antigen Bacillus anthracis tetrasaccharide[J]. Journal of Pharmaceutical Practice and Service, 2015, 33(6): 481-485,569. doi: 10.3969/j.issn.1006-0111.2015.06.001
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Research progress in the synthesis of antigen Bacillus anthracis tetrasaccharide

doi: 10.3969/j.issn.1006-0111.2015.06.001

  • Department of Organic Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

  • Received Date: 2014-04-03
  • Rev Recd Date: 2014-07-11
  • Objective Anthrax is an anthropozoonosis caused by the bacterium Bacillus anthracis. Bacillus anthracis is an aerobic, spore-forming, rod-shaped bacterium, which infects human through ingestion or inhalation of the spores. The exosporium of spores of Bacillus anthracis contains tetrasaccharide antigen with specific chemical structure, which can be used in preparation of glycoconjugates vaccines, inducing an immune response. This paper reviewed articles in the last decade that reported research advances in chemical synthesis of anthrax tetrasaccharide, presented the methods for synthesis, and compared the advantages and limitations among different methods.
  • [1] Mock M, Fouet A. Anthrax[J]. Annu Rev Microbiol, 2001,55:647-671.
    [2] Nicholson WL, Munakata N, Horneck G, et al. Resistance of Bacillus endospores to extreme terrestrial and extraterrestrial environments[J]. MMBR, 2000,64(3):548-572.
    [3] Bouzianas DG. Current and future medical approaches to combat the anthrax threat[J]. J Med Chem, 2010,53(11):4305-4331.
    [4] Turnbull PC. Current status of immunization against anthrax: old vaccines may be here to stay for a while[J]. Curr Opin Infect Dis, 2000,13(2):113-120.
    [5] Roy R. New trends in carbohydrate-based vaccines[J]. Drug Discov Today: Techn, 2004,1(3):327-336.
    [6] Hecht ML, Stallforth P, Silva DV, et al. Recent advances in carbohydrate-based vaccines[J]. Curr Opin Chem Biol, 2009,13(3):354-359.
    [7] Schofield L, Hewitt MC, Evans K, et al. Synthetic GPI as a candidate anti-toxic vaccine in a model of malaria[J]. Nature, 2002,418(6899):785-789.
    [8] Verez-Bencomo V, Fernandez-Santana V, Hardy E,et al. A synthetic conjugate polysaccharide vaccine against Haemophilus influenzae type b[J]. Science, 2004,305(5683):522-525.
    [9] Daubenspeck JM, Zeng H, Chen P,et al. Novel oligosaccharide side chains of the collagen-like region of BclA, the major glycoprotein of the Bacillus anthracis exosporium[J]. J Biolog Chem, 2004,279(30):30945-30953.
    [10] Wong CH. Carbohydrate-based drug discovery[M]. New York: Wiley-VCH Verlag GmbH, 2003:45-50.
    [11] Werz DB, Seeberger PH. Total synthesis of antigen Bacillus anthracis tetrasaccharide-creation of an anthrax vaccine candidate[J]. Angew Chem Int Edit, 2005,44(39):6315-6318.
    [12] Adamo R, Saksena R, Kovac P. Synthesis of the beta anomer of the spacer-equipped tetrasaccharide side chain of the major glycoprotein of the Bacillus anthracis exosporium[J]. Carbohydr Res, 2005,340(17):2579-2582.
    [13] Adamo R, Saksena R, Kovac P. Studies towards a conjugate vaccine for anthrax: synthesis of the tetrasaccharide side chain of the Bacillus anthracis exosporium[J]. Helv Chim Acta, 2006,89(6):1075-1089.
    [14] Guo H, O'Doherty GA. De novo asymmetric synthesis of the anthrax tetrasaccharide by a palladium-catalyzed glycosylation reaction[J]. Angew Chem Int Edit, 2007,46(27):5206-5208.
    [15] Guo H, O'Doherty GA. De novo asymmetric synthesis of anthrax tetrasaccharide and related tetrasaccharide[J]. J Organ Chem, 2008,73(14):5211-5220.
    [16] Crich D, Vinogradova O. Synthesis of the antigenic tetrasaccharide side chain from the major glycoprotein of Bacillus anthracis exosporium[J]. J Organ Chem, 2007,72(17):6513-6520.
    [17] Wang Y, Liang X, Wang PF. Concise synthesis of Bacillus anthracis exosporium tetrasaccharide via two-stage activation of allyl glycosyl donor strategy[J]. Tetrahedr Lett, 2011,52(30):3912-3915.
    [18] Milhomme O, Dhénin SG, Djedaini-Pilard F, et al. Synthetic studies toward the anthrax tetrasaccharide: alternative synthesis of this antigen[J]. Carbohydr Res, 2012,356:115-131.
    [19] Milhomme O, Kohler SM, Ropartz D, et al. Synthesis and immunochemical evaluation of a non-methylated disaccharide analogue of the anthrax tetrasaccharide[J]. Organ Biomolecul Chem, 2012,10(42):8524-8532.
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Research progress in the synthesis of antigen Bacillus anthracis tetrasaccharide

doi: 10.3969/j.issn.1006-0111.2015.06.001
  • Department of Organic Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China
  • Received Date: 2014-04-03
  • Rev Recd Date: 2014-07-11

Abstract: Objective Anthrax is an anthropozoonosis caused by the bacterium Bacillus anthracis. Bacillus anthracis is an aerobic, spore-forming, rod-shaped bacterium, which infects human through ingestion or inhalation of the spores. The exosporium of spores of Bacillus anthracis contains tetrasaccharide antigen with specific chemical structure, which can be used in preparation of glycoconjugates vaccines, inducing an immune response. This paper reviewed articles in the last decade that reported research advances in chemical synthesis of anthrax tetrasaccharide, presented the methods for synthesis, and compared the advantages and limitations among different methods.

HUANG Lei, XU Kehan, WU Junqi, YAO Kuo, YU Shichong, WU Qiuye. Research progress in the synthesis of antigen Bacillus anthracis tetrasaccharide[J]. Journal of Pharmaceutical Practice and Service, 2015, 33(6): 481-485,569. doi: 10.3969/j.issn.1006-0111.2015.06.001
Citation: HUANG Lei, XU Kehan, WU Junqi, YAO Kuo, YU Shichong, WU Qiuye. Research progress in the synthesis of antigen Bacillus anthracis tetrasaccharide[J]. Journal of Pharmaceutical Practice and Service, 2015, 33(6): 481-485,569. doi: 10.3969/j.issn.1006-0111.2015.06.001
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