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bioRxiv · 10.1101/2020.03.13.990838

Synthesis of Glycoconjugates Utilizing the Regioselectivity of a Lytic Polysaccharide Monooxygenase

Westereng, B.·Kracun, S. K.·Leivers, S.·Arntzen, M.·Aachmann, F. L.·Eijsink, V. G. H.
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Abstract

Polysaccharides from plant biomass are the most abundant renewable chemicals on Earth and can potentially be converted to a wide variety of useful glycoconjugates. While anomeric hydroxyl groups of carbohydrates are amenable to a variety of useful chemical modifications, selective cross-coupling to non-reducing ends has remained challenging. Several lytic polysaccharide monooxygenases (LPMOs), powerful enzymes known for their application in cellulose degradation, specifically oxidize non-reducing ends, introducing carbonyl groups that can be utilized for chemical coupling. This study provides a simple and highly specific approach to produce oxime-based glycoconjugates from LPMO-functionalized oligosaccharides. The products are evaluated by HPLC, mass spectrometry and NMR. Furthermore, we demonstrate potential biodegradability of these glycoconjugates using selective enzymes.

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Westereng, B., Kracun, S. K., Leivers, S., Arntzen, M., Aachmann, F. L., Eijsink, V. G. H.. 2020-03-15. Synthesis of Glycoconjugates Utilizing the Regioselectivity of a Lytic Polysaccharide Monooxygenase. https://doi.org/10.1101/2020.03.13.990838

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