Comparison of glycosyl donors: a supramer approach

Submitting author affiliation:
N.D. Zelinsky Institute of Organic Chemistry RAS, Moscow, Russian Federation

Beilstein Arch. 2023, 202339.

Published 26 Sep 2023

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Development of new methods of chemical glycosylation commonly includes comparison of various glycosyl donors. An attempted comparison of chemical properties of two sialic acid based thioglycoside glycosyl donors, differing only in substituent at O-9 (trifluoroacetyl vs. chloroacetyl), at different concentrations (0.05 and 0.15 mol·L–1) lead to mutually excluding conclusions concerning their relative reactivity and selectivity, which prevented us from revealing a possible influence of remote protective groups at O-9 on glycosylation outcome. According to the results of the supramer analysis of the reaction solutions, this issue might be related to formation of supramers of glycosyl donors differing in structure hence chemical properties. These results seem to imply that comparison of chemical properties of different glycosyl donors may not be as simple and straightforward as it is usually considered.

Keywords: glycosylation; sialic acids; protecting groups; concentration; reactivity; stereoselectivity

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Orlova, A. V.; Malysheva, N. N.; Panova, M. V.; Podvalnyy, N. M.; Medvedev, M. G.; Kononov, L. O. Beilstein Arch. 2023, 202339. doi:10.3762/bxiv.2023.39.v1

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