Total synthesis of mycobacterial arabinogalactan containing 92 monosaccharide units

Yong Wu, Xiong De-Cai, Si-Cong Chen, Yong-Shi Wang and Xin-Shan Ye ()
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Yong Wu: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University
Xiong De-Cai: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University
Si-Cong Chen: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University
Yong-Shi Wang: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University
Xin-Shan Ye: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University

Nature Communications, 2017, vol. 8, issue 1, 1-7

Abstract: Abstract Carbohydrates are diverse bio-macromolecules with highly complex structures that are involved in numerous biological processes. Well-defined carbohydrates obtained by chemical synthesis are essential to the understanding of their functions. However, synthesis of carbohydrates is greatly hampered by its insufficient efficiency. So far, assembly of long carbohydrate chains remains one of the most challenging tasks for synthetic chemists. Here we describe a highly efficient assembly of a 92-mer polysaccharide by the preactivation-based one-pot glycosylation protocol. Several linear and branched oligosaccharide/polysaccharide fragments ranging from 5-mer to 31-mer in length have been rapidly constructed in one-pot manner, which enables the first total synthesis of a biologically important mycobacterial arabinogalactan through a highly convergent [31+31+30] coupling reaction. Our results show that the preactivation-based one-pot glycosylation protocol may provide access to the construction of long and complicated carbohydrate chains.

Date: 2017
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DOI: 10.1038/ncomms14851

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