Automated glycan assembly of arabinomannan oligosaccharides from Mycobacterium tuberculosis

Alonso Pardo-Vargas; Priya Bharate; Martina Delbianco; Peter H Seeberger

doi:10.3762/bjoc.15.288

Automated glycan assembly of arabinomannan oligosaccharides from Mycobacterium tuberculosis

Beilstein J Org Chem. 2019 Dec 6:15:2936-2940. doi: 10.3762/bjoc.15.288. eCollection 2019.

Authors

Alonso Pardo-Vargas^{1

2}, Priya Bharate¹, Martina Delbianco¹, Peter H Seeberger^{1

2}

Affiliations

¹ Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany.
² Institute of Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, 14195 Berlin, Germany.

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.

Keywords: arabinomannan; automated glycan assembly; capping.