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炭疽杆菌表面四糖抗原全合成的研究进展

黄蕾 许克寒 吴俊琪 姚阔 俞世冲 吴秋业

黄蕾, 许克寒, 吴俊琪, 姚阔, 俞世冲, 吴秋业. 炭疽杆菌表面四糖抗原全合成的研究进展[J]. 药学实践与服务, 2015, 33(6): 481-485,569. doi: 10.3969/j.issn.1006-0111.2015.06.001
引用本文: 黄蕾, 许克寒, 吴俊琪, 姚阔, 俞世冲, 吴秋业. 炭疽杆菌表面四糖抗原全合成的研究进展[J]. 药学实践与服务, 2015, 33(6): 481-485,569. doi: 10.3969/j.issn.1006-0111.2015.06.001
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

炭疽杆菌表面四糖抗原全合成的研究进展

doi: 10.3969/j.issn.1006-0111.2015.06.001
基金项目: 国家科技重大专项(No.2012ZX09502001-005,2011ZXJ09201-012);国家自然科学基金青年项目(No.21202200);第二军医大学药学院大学生科研训练计划项目

Research progress in the synthesis of antigen Bacillus anthracis tetrasaccharide

  • 摘要: 炭疽是由炭疽杆菌引起的人畜共患的传染病。炭疽杆菌属于需氧芽孢杆菌属,为G+菌,其病原体是芽孢。炭疽芽孢最外层含有特定结构的四糖抗原,可用于制备糖缀合物疫苗,诱导免疫反应。综述近10年来文献报道对炭疽四糖化学合成的研究进展,并结合国内外最新研究成果介绍各条制备路线,比较各种方法的主要优缺点。
  • [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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    [2] 陈炳辰, 王思真, 郭贝贝, 杨峰.  紫杉醇棕榈酸酯的合成及其脂质体的制备与处方研究 . 药学实践与服务, 2024, 42(9): 379-384, 410. doi: 10.12206/j.issn.2097-2024.202404062
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  • 收稿日期:  2014-04-03
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炭疽杆菌表面四糖抗原全合成的研究进展

doi: 10.3969/j.issn.1006-0111.2015.06.001
    基金项目:  国家科技重大专项(No.2012ZX09502001-005,2011ZXJ09201-012);国家自然科学基金青年项目(No.21202200);第二军医大学药学院大学生科研训练计划项目

摘要: 炭疽是由炭疽杆菌引起的人畜共患的传染病。炭疽杆菌属于需氧芽孢杆菌属,为G+菌,其病原体是芽孢。炭疽芽孢最外层含有特定结构的四糖抗原,可用于制备糖缀合物疫苗,诱导免疫反应。综述近10年来文献报道对炭疽四糖化学合成的研究进展,并结合国内外最新研究成果介绍各条制备路线,比较各种方法的主要优缺点。

English Abstract

黄蕾, 许克寒, 吴俊琪, 姚阔, 俞世冲, 吴秋业. 炭疽杆菌表面四糖抗原全合成的研究进展[J]. 药学实践与服务, 2015, 33(6): 481-485,569. doi: 10.3969/j.issn.1006-0111.2015.06.001
引用本文: 黄蕾, 许克寒, 吴俊琪, 姚阔, 俞世冲, 吴秋业. 炭疽杆菌表面四糖抗原全合成的研究进展[J]. 药学实践与服务, 2015, 33(6): 481-485,569. doi: 10.3969/j.issn.1006-0111.2015.06.001
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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