Synthesis of glycoconjugates utilizing the regioselectivity of a lytic polysaccharide monooxygenase

• Published in: Scientific reports Vol. 10; no. 1; p. 13197
• Main Authors: Westereng, Bjørge, Kračun, Stjepan K., Leivers, Shaun, Arntzen, Magnus Ø., Aachmann, Finn L., Eijsink, Vincent G. H.
• Format: Journal Article
• Language: English
• Published: London Nature Publishing Group UK 06.08.2020; Nature Publishing Group
• Subjects: 631/45; 631/61; 631/92; 639/638; Biodegradability; Biodegradation; Carbohydrate Sequence; Carbohydrates; Carbonyl compounds; Cellulose; Chemistry Techniques, Synthetic; Drug delivery; Enzymes; Glycoconjugates; Glycoconjugates - chemical synthesis; Glycoconjugates - chemistry; High-performance liquid chromatography; Humanities and Social Sciences; Liquid chromatography; Mass spectrometry; Mass spectroscopy; Mixed Function Oxygenases - metabolism; Monooxygenase; multidisciplinary; NMR; Nuclear magnetic resonance; Oligosaccharides; Plant biomass; Polysaccharides; Polysaccharides - metabolism; Saccharides; Science; Science (multidisciplinary); Stereoisomerism; Substrate Specificity; Vaccine development
• ISSN: 2045-2322; 2045-2322
• DOI: 10.1038/s41598-020-69951-7

Polysaccharides from plant biomass are the most abundant renewable chemicals on Earth and can potentially be converted to a wide variety of useful glycoconjugates. Potential applications of glycoconjugates include therapeutics and drug delivery, vaccine development and as fine chemicals. 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.