Unravelling the structure of glycosyl cations via cold-ion infrared spectroscopy

Eike Mucha, Mateusz Marianski, Fei-Fei Xu, Daniel A. Thomas, Gerard Meijer, Gert von Helden, Peter H. Seeberger () and Kevin Pagel ()
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Eike Mucha: Fritz Haber Institute of the Max Planck Society
Mateusz Marianski: Fritz Haber Institute of the Max Planck Society
Fei-Fei Xu: Max Planck Institute of Colloids and Interfaces
Daniel A. Thomas: Fritz Haber Institute of the Max Planck Society
Gerard Meijer: Fritz Haber Institute of the Max Planck Society
Gert von Helden: Fritz Haber Institute of the Max Planck Society
Peter H. Seeberger: Freie Universität Berlin
Kevin Pagel: Fritz Haber Institute of the Max Planck Society

Nature Communications, 2018, vol. 9, issue 1, 1-5

Abstract: Abstract Glycosyl cations are the key intermediates during the glycosylation reaction that covalently links building blocks during the synthetic assembly of carbohydrates. The exact structure of these ions remained elusive due to their transient and short-lived nature. Structural insights into the intermediate would improve our understanding of the reaction mechanism of glycosidic bond formation. Here, we report an in-depth structural analysis of glycosyl cations using a combination of cold-ion infrared spectroscopy and first-principles theory. Participating C2 protective groups form indeed a covalent bond with the anomeric carbon that leads to C1-bridged acetoxonium-type structures. The resulting bicyclic structure strongly distorts the ring, which leads to a unique conformation for each individual monosaccharide. This gain in mechanistic understanding fundamentally impacts glycosynthesis and will allow to tailor building blocks and reaction conditions in the future.

Date: 2018
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DOI: 10.1038/s41467-018-06764-3

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