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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

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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
shu
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
shu

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

  • 第二军医大学药学院有机化学教研室, 上海 200433

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

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

  • 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。
    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.
  • [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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出版历程
  • 收稿日期:  2014-04-03
  • 修回日期:  2014-07-11

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
  • 第二军医大学药学院有机化学教研室, 上海 200433
    • 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
  • 收稿日期: 2014-04-03
  • 修回日期: 2014-07-11

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
shu
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
shu

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