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Total synthesis of dansyl and biotin functionalized ganglioside GM3 by chemoenzymatic method

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Abstract

Ganglioside GM3, as well as other gangliosides, offers a variety of modifications in its sialic acid and ceramide moieties GM3 exhibits various types of important biological activities, due to the inability to effectively observe the trafficking of ganglioside GM3, developing sensitive research tools for specific monitoring of GM3 expression and activity is thus desirable. The total synthesis of a dansyl and biotin bifunctionalized fluorescent ganglioside GM3 were reported in this article. From lactose after 13 reaction steps, the compound of 2″-biotinoylaminoethyl-6-N-dansylamido-6-deoxy-β-D-galatopyranosyl-(1→4)-β-D-glucopy-ranoside was obtained in total yield of 16.2%. Sialylation of dansyl and biotin functionalized lactose by enzymatic method gave dansyl and biotin labeled ganglioside GM3. The fluorescent property of this compound was also investigated.

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Authors and Affiliations

  1. Research Center of Medicinal Chemistry & Chemical Biology, Chongqing Key Laboratory of Catalysis and Functional Organic Molecules, Chongqing Technology and Business University, Chongqing, 400067, China

    Bin Sun & HeYan Jiang

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  1. Bin Sun
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  2. HeYan Jiang
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Correspondence to Bin Sun.

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Sun, B., Jiang, H. Total synthesis of dansyl and biotin functionalized ganglioside GM3 by chemoenzymatic method. Sci. China Chem. 56, 933–938 (2013). https://doi.org/10.1007/s11426-013-4838-4

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  • DOI: https://doi.org/10.1007/s11426-013-4838-4

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