Affiliation:
1. Department of Biomolecular Systems Max-Planck Institute of Colloids and Interfaces Am Mühlenberg 1 14476 Potsdam Germany
2. Department of Chemistry and Biochemistry Freie Universität Berlin Arnimallee 22 14195 Berlin Germany
3. GlycoUniverseGmbH&Co.KGaA Am Mühlenberg 11 14476 Potsdam Germany
Abstract
AbstractThe chemical synthesis of complex oligosaccharides relies on efficient and highly reproducible glycosylation reactions. The outcome of a glycosylation is contingent upon several environmental factors, such as temperature, acidity, the presence of residual moisture, as well as the steric, electronic, and conformational aspects of the reactants. Each glycosylation proceeds rapidly and with a high yield within a rather narrow temperature range. For better control over glycosylations and to ensure fast and reliable reactions, a systematic analysis of 18 glycosyl donors revealed the effect of reagent concentration, water content, protecting groups, and structure of the glycosyl donors on the activation temperature. With these insights, we parametrize the first step of the glycosylation reaction to be executed reliably and efficiently.
Funder
H2020 Marie Skłodowska-Curie Actions