Novel chemical tools to elucidate carbohydrate chemistry

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Complex carbohydrates are among the most versatile biomolecules, playing diverse and essential roles in virtually every living system. Additionally, as key mediators in biological processes, they form the basis for the development of glycomimetic drugs and vaccines.Due to the absence of amplification techniques and expression systems, chemical synthesis offers the most efficient way to access glycans in pure form. The complex and time consuming syntheses have been significantly accelerated by the development of automated glycan assembly by WG Seeberger, providing straightforward access to a wide variety of glycans. However, the detailed mechanism of the glycosidic bond formation – the elementary reaction in glycan synthesis – remains poorly understood. Two limitations exist in the study of these mechanistically rich and structurally complex linkage reactions: the controlled, reproducible optimization of each new coupling, and rapid, data-rich analytics.The joint project of WG Seeberger and WG Pagel aims at the better understanding of the underlying mechanisms of glycosidic bond formation. WG Seeberger will utilize the controlled microreactor synthesis platform to optimize experimental parameters and conditions. The resulting changes in identity and proportion of intermediates, products and byproducts will afterwards be probed by ion mobility-mass spectrometry in WG Pagel. The systematic analysis of the resulting comprehensive dataset will expand the knowledge about glycan intermediates and form the basis for their development of predictive models for glycosylation reactions.