Programmable intermediate-controlled sialylation reactions

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1st EuroCarb Young Researcher (ECYR) Workshop

CarboMet Workshop

Mini symposium: Glycobiology at the LUMC and beyond

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Programmable intermediate-controlled sialylation reactions

Kesatebrhan Haile Asressu 1,2,3 , Chun-Wei Chang 1,4,5 , Sarah Lam 6 , Cheng-Chung Wang 1,2,4

1 Institute of Chemistry, Academia Sinica, Taipei , Taiwan, 2 Taiwan International Graduate Program (TIGP), Sustainable Chemical Science and Technology (SCST), Academia Sinica, Taipei, Taiwan, 3 Applied Chemistry Department, National Chiao Tung University , Hsinchu , Taiwan, 4 Chemical Biology and Molecular Biophysics Program, Taiwan International Graduate Program (TIGP), Academia Sinica, Taipei, Taiwan, 5 Department of Chemistry, National Taiwan University, Taipei , Taiwan, 6Institute of Condensed Matter and Nanosciences, Université Catholique de Louvain, Louvain-la-Neuve, Belgium

Although tremendous efforts have been made for the efficient preparation of natural sialosides, controlling the stereochemical outcome of sialylation is still the most challenging task. Herein, we developed a new strategy performing high stereoselectivity and yield of O-sialylation on several p-tolyl thiosialosides in NIS/TfOH system by using their corresponding RRV as an indicator. In the reaction mechanism, we further confirmed that unexpected glycosyl halide intermediates were generated with the participation of halogens by using low temperature NMR technique, which greatly enhanced the α-selectivity. Eventually, a precise mechanism was proposed with numerous crucial factors including donor functionalities, acceptors, promoters (NXS, X = Cl, Br, I), temperature, and activation time.

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