Faculty of Chemistry, Biotechnology and Food Science, NMBU-Norwegian University of Life Sciences, Chr. M. Falsens vei 1, Ås, Norway.
Department of Plant and Environmental Sciences, University of Copenhagen, Thorvaldsensvej 40, 1871, Frederiksberg C, Denmark.
Sci Rep. 2020 Aug 6;10(1):13197. 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.
植物生物质中的多糖是地球上最丰富的可再生化学品，它们有可能被转化为各种各样有用的糖缀合物。糖缀合物的潜在应用包括治疗和药物输送、疫苗开发以及精细化学品。虽然碳水化合物的端基羟基可适用于各种有用的化学修饰，但选择性地与非还原端交叉偶联仍然具有挑战性。几种溶菌多糖单加氧酶（LPMO）是一种强大的酶，因其在纤维素降解中的应用而闻名，它们专门氧化非还原端，引入羰基，可用于化学偶联。本研究提供了一种简单而高度特异的方法，从 LPMO 功能化的低聚糖制备肟基糖缀合物。通过 HPLC、质谱和 NMR 对产物进行评估。此外，我们还使用选择性酶证明了这些糖缀合物的潜在可生物降解性。
