Name(s) of Faculty Adviser/Mentor

Alexei V. Demchenko

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Use of automated technologies is of increasing interest in glycosciences.1 Among the new methodologies, a number of recent advancements have emerged in the area of solid-phase oligosaccharide synthesis.2-3 Demchenko and Stine developed a synthesizer based on a commercial HPLC instrument that was recently improved by the implementation of the autosampler for the delivery of glycosylation promoters.4 Despite the added versatility, the system still lacks complete automation. The foundations of glycan syntheses are acceptors and donors, grouped together under the general term of building blocks. Presented herein is the synthesis of the building blocks of the rhamno and galacto series. We then showcase how these building blocks can be used in the next generation HPLC system to build two oligosaccharides of biological interest. A split-valve and a programmable autosampler are employed to provide recirculation, and each step of the synthesis can now be fully automated. The synthesis of these target compounds illustrate the versatility and reliability of the automated technology, which is still in development at this point. The automated technology is expected to provide a quicker and more universally available way of generating glycans in the future. 1. Panza, M.; Pistorio, S. G.; Stine, K. J.; Demchenko, A. V., Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges. Chemical Reviews 2018, 118 (17), 8105-8150. 2. Krock, L.; Esposito, D.; Castagner, B.; Wang, C.-C.; Bindschadler, P.; Seeberger, P. H., Streamlined access to conjugation-ready glycans by automated synthesis. Chemical Science 2012, 3 (5), 1617-1622. 3. Ganesh, N. V.; Fujikawa, K.; Tan, Y. H.; Stine, K. J.; Demchenko, A. V., HPLC-Assisted Automated Oligosaccharide Synthesis. Organic Letters 2012, 14 (12), 3036-3039. 4. Pistorio, S. G.; Nigudkar, S. S.; Stine, K. J.; Demchenko, A. V., HPLC-Assisted Automated Oligosaccharide Synthesis: Implementation of the Autosampler as a Mode of the Reagent Delivery. The Journal of Organic Chemistry 2016, 81 (19), 8796-8805.

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