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Synthesis of 1,2,3-Triazolo-Linked Octyl (1→6)-α-d-Oligomannosides and Their Evaluation in Mycobacterial Mannosyltransferase Assay

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    Synthesis of 1,2,3-Triazolo-Linked Octyl (1→6)-α-d-Oligomannosides and Their Evaluation in Mycobacterial Mannosyltransferase Assay
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    † Institute of Chemistry, Center for Glycomics, GLYCOMED, Slovak Academy of Sciences, Dúbravská cesta 9, SK-845 38 Bratislava, Slovakia
    ‡ Department of Biochemistry, Faculty of Natural Sciences, Comenius University, Mlynská dolina, CH1, SK-842 15 Bratislava, Slovakia
    § Department of Chemistry, University of Manitoba, 144 Dysart Road, Winnipeg, Manitoba R3T 2N2, Canada
    *Corresponding author. Tel: +421 259410272. Fax: +421 259410222. E-mail address: [email protected]
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    Bioconjugate Chemistry

    Cite this: Bioconjugate Chem. 2011, 22, 2, 289–298
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    https://doi.org/10.1021/bc100421g
    Published January 20, 2011
    Copyright © 2011 American Chemical Society
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    Abstract

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    The synthesis of conjugates consisting of two or three mannose units interconnected by a 1,2,3-triazole linker installed by the “click” reaction is reported. These conjugates were evaluated in mycobacterial mannosyltransferase (ManT) assay. Detailed analysis of the reaction products showed that these compounds with triazole linker between sugar moieties were tolerated by the enzyme, which elongated them by one or two sugar units with α-(1→6) linkage. The effectiveness of this transfer was reduced in comparison to that observed for the acceptor analogues containing a glycosidic linkage, but still, this is the first report on such unnatural compounds serving as substrates for mycobacterial ManT. The ability of the studied compounds to function as acceptors for the ManT suggests that the relative distance and spatial orientation of acceptor octyl hydrophobic aglycone (optimal length for the ManT) and free primary C-6 hydroxy group of the nonreducing terminal mannose unit (to which glycosyl residue is transferred by the mycobacterial ManT) are important for ManT activity, but at the same time, their variations are tolerated by the enzyme in a relatively wide range.

    Copyright © 2011 American Chemical Society

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    1H NMR and 13C NMR spectra of compounds 2, 3, 7, 8, 9, 10, 11, 12, and 13. Figure S1. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cite this: Bioconjugate Chem. 2011, 22, 2, 289–298
    Click to copy citationCitation copied!
    https://doi.org/10.1021/bc100421g
    Published January 20, 2011
    Copyright © 2011 American Chemical Society
    Request reuse permissions

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