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肿瘤相关糖抗原GM3及其衍生物合成方法研究进展

白国静 边晓杰 姚阔 吴俊琪 俞世冲 孟庆国 吴秋业

白国静, 边晓杰, 姚阔, 吴俊琪, 俞世冲, 孟庆国, 吴秋业. 肿瘤相关糖抗原GM3及其衍生物合成方法研究进展[J]. 药学实践与服务, 2016, 34(1): 5-7,15. doi: 10.3969/j.issn.1006-0111.2016.01.002
引用本文: 白国静, 边晓杰, 姚阔, 吴俊琪, 俞世冲, 孟庆国, 吴秋业. 肿瘤相关糖抗原GM3及其衍生物合成方法研究进展[J]. 药学实践与服务, 2016, 34(1): 5-7,15. doi: 10.3969/j.issn.1006-0111.2016.01.002
BAI Guojing, BIAN Xiaojie, YAO Kuo, WU Junqi, YU Shichong, MENG Qingguo, WU Qiuye. Research progress in the synthesis of tumor-associated carbohydrate antigens (TACAs) GM3 and derivatives[J]. Journal of Pharmaceutical Practice and Service, 2016, 34(1): 5-7,15. doi: 10.3969/j.issn.1006-0111.2016.01.002
Citation: BAI Guojing, BIAN Xiaojie, YAO Kuo, WU Junqi, YU Shichong, MENG Qingguo, WU Qiuye. Research progress in the synthesis of tumor-associated carbohydrate antigens (TACAs) GM3 and derivatives[J]. Journal of Pharmaceutical Practice and Service, 2016, 34(1): 5-7,15. doi: 10.3969/j.issn.1006-0111.2016.01.002

肿瘤相关糖抗原GM3及其衍生物合成方法研究进展

doi: 10.3969/j.issn.1006-0111.2016.01.002
基金项目: 国家自然科学基金青年项目(21202200),国家科技部重大专项重大新药创制(2012ZX09502001-005),第二军医大学本科生创新基金项目

Research progress in the synthesis of tumor-associated carbohydrate antigens (TACAs) GM3 and derivatives

  • 摘要: GM3及其衍生物合成中的糖苷化反应条件苛刻,端基碳的立体构型较难控制,能否高效地得到α糖苷键是评价反应优劣的重要标志之一。笔者综述了近年来GM3及其衍生物的合成方法,涉及糖供体化合物的选择、糖受体的确定、立体选择性的控制及新糖苷化反应催化剂的发展。
  • [1] Yamakawa T, Suzuki S. The chemistry of the lipids of posthemolytic residue or stroma of erythrocytes I concerning the ether-insoluble lipids of lyophilized horse Bblood stroma [J]. J Biochem, 1951, 38 (2): 199-212.
    [2] Giussani P, Tringali C, Riboni L, et al. Sphingolipids: key regulators of apoptosis and pivotal players in cancer drug resistance [J]. Int J Mol Sci, 2014, 15 (3): 4356-4392.
    [3] Tringali C, Silvestri I, Testa F, et al. Molecular subtyping of metastatic melanoma based on cell ganglioside metabolism profiles [J]. BMC cancer, 2014, 14 (1): 560.
    [4] Duclos JR. The total synthesis of ganglioside GM3 [J]. Carbohydr Res, 2000, 328 (4): 489-507.
    [5] Imamura A, Yoshikawa T, Komori T, et al. Design and synthesis of versatile ganglioside probes for carbohydrate microarrays [J]. Glycoconj J, 2008, 25 (3): 269-278.
    [6] Zheng M, Ye XS. Synthesis of N-modified ganglioside GM3 derivatives [J]. Tetrahedron Lett, 2012, 68 (5): 1475-1482.
    [7] 李相鹏, 王 鹏, 李英霞. 全乙酰 GM3 三糖对甲氧基苯酚苷的合成[J].合成化学, 2010, 18 (5): 538-542.
    [8] Chefalo P, Pan Y, Nagy N, et al. Harding CV. Efficient metabolic engineering of GM3 on tumor cells by N-phenylacetyl-D-mannosamine [J]. J Biochem, 2006, 45 (11): 3733-3739.
    [9] Yu S, Wang Q, Zhang J, et al. Synthesis and evaluation of protein conjugates of GM3 derivatives carrying modified sialic acids as highly immunogenic cancer vaccine candidates [J]. Medchemcomm, 2011, 2 (6): 524-530.
    [10] Wang Q, Zhou Z, Tang S, et al. Carbohydrate-monophosphoryl lipid A conjugates are fully synthetic self-adjuvanting cancer vaccines eliciting robust immune responses in the mouse [J]. ACS Chem Biol, 2011, 7 (1): 235-240.
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    [12] Pan Y, Chefalo P, Nagy N, et al. Synthesis and immunological properties of N-modified GM3 antigens as therapeutic cancer vaccines [J]. J Med Chem, 2005, 48 (3): 875-883.
    [13] Fujikawa K, Imamura A, Ishida H, et al. Synthesis of a GM3 ganglioside analogue carrying a phytoceramide moiety by intramolecular glycosylation as a key step [J]. Carbohydr Res, 2008, 343 (16): 2729-2734.
    [14] Ando H, Koike Y, Ishida H, et al. Extending the possibility of an N-Troc-protected sialic acid donor toward variant sialo-glycoside synthesis [J]. Tetrahedron Lett, 2003, 44 (36): 6883-6.
    [15] Ando H,Ishida H,Kiso M,et al.A synthetic approach to the c-series gangliosides containing sialyl-α (2→8) sialyl-α (2→8) sialic acid: Synthesis of ganglioside GT4,α (2→6) GT4 and GT3[J].Carbohydr Res,1997,300(3):207-217.
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    [17] Sun B, Jiang H. Total synthesis of dansyl and biotin functionalized ganglioside GM3 by chemoenzymatic method [J]. Sci China Chem, 2013, 56 (7): 933-938.
    [18] Sun B, Jiang H. An efficient approach for total synthesis of aminopropyl functionalized ganglioside GM1b [J]. Tetrahedron Lett, 2012, 53 (42): 5711-5715.
    [19] Sun B, Yang B, Huang X. Total synthesis of the aminopropyl functionalized ganglioside GM1 [J]. Sci China Chem, 2012, 55 (1): 31-35.
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  • 收稿日期:  2014-12-03
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肿瘤相关糖抗原GM3及其衍生物合成方法研究进展

doi: 10.3969/j.issn.1006-0111.2016.01.002
    基金项目:  国家自然科学基金青年项目(21202200),国家科技部重大专项重大新药创制(2012ZX09502001-005),第二军医大学本科生创新基金项目

摘要: GM3及其衍生物合成中的糖苷化反应条件苛刻,端基碳的立体构型较难控制,能否高效地得到α糖苷键是评价反应优劣的重要标志之一。笔者综述了近年来GM3及其衍生物的合成方法,涉及糖供体化合物的选择、糖受体的确定、立体选择性的控制及新糖苷化反应催化剂的发展。

English Abstract

白国静, 边晓杰, 姚阔, 吴俊琪, 俞世冲, 孟庆国, 吴秋业. 肿瘤相关糖抗原GM3及其衍生物合成方法研究进展[J]. 药学实践与服务, 2016, 34(1): 5-7,15. doi: 10.3969/j.issn.1006-0111.2016.01.002
引用本文: 白国静, 边晓杰, 姚阔, 吴俊琪, 俞世冲, 孟庆国, 吴秋业. 肿瘤相关糖抗原GM3及其衍生物合成方法研究进展[J]. 药学实践与服务, 2016, 34(1): 5-7,15. doi: 10.3969/j.issn.1006-0111.2016.01.002
BAI Guojing, BIAN Xiaojie, YAO Kuo, WU Junqi, YU Shichong, MENG Qingguo, WU Qiuye. Research progress in the synthesis of tumor-associated carbohydrate antigens (TACAs) GM3 and derivatives[J]. Journal of Pharmaceutical Practice and Service, 2016, 34(1): 5-7,15. doi: 10.3969/j.issn.1006-0111.2016.01.002
Citation: BAI Guojing, BIAN Xiaojie, YAO Kuo, WU Junqi, YU Shichong, MENG Qingguo, WU Qiuye. Research progress in the synthesis of tumor-associated carbohydrate antigens (TACAs) GM3 and derivatives[J]. Journal of Pharmaceutical Practice and Service, 2016, 34(1): 5-7,15. doi: 10.3969/j.issn.1006-0111.2016.01.002
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