A Single Route to Mammalian N-Glycans Substituted with Core Fucose and Bisecting GlcNAc

Angewandte Chemie
Thomas LuberCarlo Unverzagt

Abstract

The occurrence of α1,6-linked core fucose on the N-glycans of mammalian glycoproteins is involved in tumor progression and reduces the bioactivity of antibodies in antibody-dependent cell-mediated cytotoxicity (ADCC). Since core-fucosylated N-glycans are difficult to isolate from natural sources, only chemical or enzymatic synthesis can provide the desired compounds for biological studies. A general drawback of chemical α-fucosylation is that the chemical assembly of α1,6-linked fucosides is not stereospecific. A robust and general method for the α-selective fucosylation of acceptors with primary hydroxy groups in α/β ratios exceeding 99:1 was developed. The high selectivities result from the interplay of an optimized protecting group pattern of the fucosyl donors in combination with the activation principle and the reaction conditions. Selective deprotection yielded versatile azides of all mammalian complex-type core-fucosylated N-glycans with 2-4 antennae and optional bisecting GlcNAc.

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Citations

Jul 29, 2020·Frontiers in Chemistry·Qiushi ChenYan Ren
Jul 1, 2020·Chembiochem : a European Journal of Chemical Biology·Michael WeissCarlo Unverzagt
Mar 7, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Asuka ShirakawaKoichi Fukase
Feb 5, 2019·Journal of the American Chemical Society·Larissa Krasnova, Chi-Huey Wong
Sep 15, 2021·Angewandte Chemie·Asuka ShirakawaKoichi Fukase

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