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

MPS-Authors

Kottari,  Naresh
Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Schuhmacher,  Frank
Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Hahm,  Heung Sik
Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Seeberger,  Peter H.
Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Citation

Kottari, N., Schuhmacher, F., Hahm, H. S., & Seeberger, P. H. (2017). Pushing the limits of automated glycan assembly: synthesis of a 50mer polymannoside. Chemical Communications, 53(65), 9085-9088. doi:10.1039/C7CC04380E.


Cite as: http://hdl.handle.net/11858/00-001M-0000-002D-A51F-3
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 product. The synthesis of long polymers serves as the ultimate test of the efficiency and reliability of synthetic processes. A series of Man-(1[rightward arrow]6)-[small alpha]-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.