Journal article
Synthesis of C-Mannosylated Glycopeptides Enabled by Ni-Catalyzed Photoreductive Cross-Coupling Reactions
R Mao, S Xi, S Shah, MJ Roy, A John, JP Lingford, G Gäde, NE Scott, ED Goddard-Borger
Journal of the American Chemical Society | Published : 2021
DOI: 10.1021/jacs.1c05567
Abstract
The biological functions of tryptophan C-mannosylation are poorly understood, in part, due to a dearth of methods for preparing pure glycopeptides and glycoproteins with this modification. To address this issue, efficient and scalable methods are required for installing this protein modification. Here, we describe unique Ni-catalyzed cross-coupling conditions that utilize photocatalysis or a Hantzsch ester photoreductant to couple glycosyl halides with (hetero)aryl bromides, thereby enabling the α-C-mannosylation of 2-bromo-tryptophan, peptides thereof, and (hetero)aryl bromides more generally. We also report that 2-(α-d-mannopyranosyl)-L-tryptophan undergoes facile anomerization in the pres..
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Awarded by Australian Research Council
Funding Acknowledgements
We would like to thank Dr. Martin Brzozowski for the generous gift of 4CzIPN and the Melbourne Mass Spectrometry and Proteomics Facility of The Bio21 Molecular Science and Biotechnology Institute at The University of Melbourne for assistance with mass spectrometry analyses. We would like to acknowledge support from The Walter and Eliza Hall Institute of Medical Research; National Health and Medical Research Council of Australia (NHMRC) project grants GNT1139546, GNT1139549 and GNT2000517; ARC Discovery Project Grant DP210100362, the Australian Cancer Research Fund and a Victorian State Government Operational Infrastructure support grant. N.E.S is supported by an ARC Future Fellowship and E.D.G.B. is supported by the Brian M. Davis Charitable Foundation Centenary Fellowship.