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Issue 65, 2017
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Pushing the limits of automated glycan assembly: synthesis of a 50mer polymannoside

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Abstract

Automated glycan assembly (AGA) enables rapid access to oligosaccharides. The overall length of polymers created via automated solid phase synthesis depends on very high yields at every step to obtain full length products. The synthesis of long polymers serves as the ultimate test of the efficiency and reliability of synthetic processes. A series of Man-(1 → 6)-α-Man linked oligosaccharides up to a 50mer, the longest synthetic sequence yet assembled from monosaccharides, has been realized via a 102 step synthesis. We identified a suitable mannose building block and applied a capping step in the final five AGA cycles to minimize (n − 1) deletion sequences that are otherwise difficult to remove by HPLC.

Graphical abstract: Pushing the limits of automated glycan assembly: synthesis of a 50mer polymannoside

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Publication details

The article was received on 06 Jun 2017, accepted on 17 Jul 2017 and first published on 17 Jul 2017


Article type: Communication
DOI: 10.1039/C7CC04380E
Citation: Chem. Commun., 2017,53, 9085-9088
  • Open access: Creative Commons BY license
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    Pushing the limits of automated glycan assembly: synthesis of a 50mer polymannoside

    K. Naresh, F. Schumacher, H. S. Hahm and P. H. Seeberger, Chem. Commun., 2017, 53, 9085
    DOI: 10.1039/C7CC04380E

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