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Synthesis of a tetrasaccharide repeating unit of the exopolysaccharide from Burkholderia multivorans

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journal contribution
posted on 2017-11-03, 13:28 authored by Xin Zhang, Dongyue Wang, Guoxia Jin, Lizhen Wang, Zhongwu Guo, Guofeng Gu

The chemical synthesis of a tetrasaccharide repeating unit of the exopolysaccharide discovered from Burkholderia multivorans with a 3-aminopropyl group linked to the glycan downstream end, α-D-Manp-(1→2)-α-D-Manp-(1→2)-3-O-methyl-α-D-Rhap-(1→3)-α-D-Rhap-O(CH2)3NH2 (1), was described. The target tetrasaccharide was achieved by both a convergent [2 + 2] and a linear glycosylation strategies. The latter synthesis was proved to be more efficient than the former due to the excellent stereocontrol of glycosylation. Furthermore, the 3-aminopropyl group in the target molecule would enable its conjugation with functional biomolecules to explore its biological applications.

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