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

BAI Guojing; BIAN Xiaojie; YAO Kuo; WU Junqi; YU Shichong; MENG Qingguo; WU Qiuye

doi:10.3969/j.issn.1006-0111.2016.01.002

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Glycosylation is the key step of the synthesis of GM3, its reaction conditions are very harsh, the stereoselectivities are usually poor, and the configuration of anomeric carbon is difficult to control. Whether α glycosidic bond can be constructed efficiently in sialylation reactions is an important criteria used to evaluate the reaction quality. Studies of GM3 and derivatives methods generally relates to following areas: the choice of the donor compounds and receptor compounds, the control of stereoselectivity, and the development of some new glycosidic reaction catalyst. In recent years, important progress has been made in this research area. Now, we predominately make a summary and review on the progress of methods for the synthesis of GM3 and derivatives.

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

1. College of Pharmacy, Yantai University, Yantai 264005, China;School of Pharmacy, Second Military Medical University, Shanghai 200433, China

2. School of Pharmacy, Second Military Medical University, Shanghai 200433, China

3. College of Pharmacy, Yantai University, Yantai 264005, China

Received Date: 2014-12-03

Rev Recd Date: 2015-03-27

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Abstract: Glycosylation is the key step of the synthesis of GM3, its reaction conditions are very harsh, the stereoselectivities are usually poor, and the configuration of anomeric carbon is difficult to control. Whether α glycosidic bond can be constructed efficiently in sialylation reactions is an important criteria used to evaluate the reaction quality. Studies of GM3 and derivatives methods generally relates to following areas: the choice of the donor compounds and receptor compounds, the control of stereoselectivity, and the development of some new glycosidic reaction catalyst. In recent years, important progress has been made in this research area. Now, we predominately make a summary and review on the progress of methods for the synthesis of GM3 and derivatives.

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[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.
[11]	Tang S, Wang Q, Guo Z. Synthesis of a monophosphoryl derivative of escherichia coli lipid A and its efficient coupling to a tumor-associated carbohydrate antigen [J]. Chemistry,2010, 16 (4): 1319-1325.
[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.
[16]	Kameyama A, Ishida H, Kiso M, et al. Stereoselective synthesis of sialyl-lactotetraosylceramide and sialylneo-lactotetraosylceramide [J]. Carbohydr Res, 1990, 200: 269-285.
[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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Research progress in the synthesis of tumor-associated carbohydrate antigens (TACAs) GM3 and derivatives

doi: 10.3969/j.issn.1006-0111.2016.01.002

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