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

GRAPHICAL ABSTRACT

ABSTRACT

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.

KEYWORDS:

• Burkholderia multivorans
• Exopolysaccharide
• Synthesis
• Glycosylation

Acknowledgment

This research was supported by grants from the Shandong Provincial Natural Science Foundation (No. ZR2015BM020) and the Science and Technology Development Project of Shandong Province (No. 2015GSF118019 and 2016GGH4502).

Additional information

Notes on contributors

Xin Zhang

Xin Zhang received her B.S. in Chemistry in 2013 from Dezhou University and M.S. in organic chemistry in 2016 from Shandong University. Currently, she is a research scientist at Qilu Pharmaceutical Company, Shandong, China.

Guofeng Gu

Guofeng Gu received his B.S. in Chemistry in 1999 from Shandong Normal University. He obtained his Ph.D. in organic chemistry in 2004 under the supervision of Prof. Yuguo Du at Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences. After three years of postdoctoral research at Simon Fraser University with Prof. B. Mario Pinto, he joined the National Glycoengineering Research Center of Shandong University as an Associate Professor in 2008. His research interests focus on carbohydrate chemistry and carbohydrate-based antibacterial vaccines.