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Journal Article

Automated glycan assembly of arabinomannan oligosaccharides from Mycobacterium tuberculosis

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

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Bharate,  Priya
Peter H. Seeberger - Nanoparticles and Colloidal Polymers, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Delbianco,  Martina
Martina Delbianco, 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

Pardo-Vargas, A., Bharate, P., Delbianco, M., & Seeberger, P. H. (2019). Automated glycan assembly of arabinomannan oligosaccharides from Mycobacterium tuberculosis. Beilstein Journal of Organic Chemistry, 15, 2936-2940. doi:10.3762/bjoc.15.288.


Cite as: https://hdl.handle.net/21.11116/0000-0005-5981-5
Abstract
Arabinomannan (AM) polysaccharides are clinical biomarkers for Mycobacterium tuberculosis (MTB) infections due to their roles in the interaction with host cells and interference with macrophage activation. Collections of defined AM oligosaccharides can help to improve the understanding of these polysaccharides and the development of novel therapeutical and diagnostic agents. Automated glycan assembly (AGA) was employed to prepare the core structure of AM from MTB, containing α-(1,6)-Man, α-(1,5)-Ara, and α-(1,2)-Man linkages. The introduction of a capping step after each glycosylation and further optimized reaction conditions allowed for the synthesis of a series of oligosaccharides, ranging from hexa- to branched dodecasaccharides.