1) Komura N, Kato K, Udagawa T, Asano S, Tanaka H-N, Imamura A, Ishida H, Kiso M, Ando H. Constrained sialic acid donors enable selective synthesis of α-glycosides, Science (364): 677–680, 20192) Asano S, Pal R, Tanaka H-N, Imamura A, Ishida H, Suzuki KGN, Ando H, Development of fluorescently labeled SSEA-3, SSEA-4, and Globo-H glycosphingolipids for elucidating molecular interactions in the cell membrane, Int. J. Mol. Sci. (20): 6187, 20193) Asano S, Tanaka H-N, Imamura A, Ishida H, Ando H, p-tert-Butyl groups improve the utility of aromatic protecting groups in carbohydrate synthesis, Org. Lett. (21): 4197–4200, 20194) Takahashi M, Shirasaki J, Komura N, Sasaki K, Tanaka H-N, Imamura A, Ishida H, Hanashima S, Murata M, Ando H, Efficient diversification of GM3 gangliosides via late-stage sialylation and dynamic glycan structural studies with 19F solid-state NMR, Org. Biomol. Chem. (18): 2902–2913, 20205) Takahashi M, Komura N, Yoshida Y, Yamaguchi E, Hasegawa A, Tanaka H-N, Imamura A, Ishida H, Suzuki KGN, Ando H, Development of lacto-series ganglioside fluorescent probe usinglate-stage sialylation and behavior analysis with single-molecule imaging, RSC Chem. Biol. 2022 accepted.4. Future perspectivesA substituent of the sialic acid, the C-1 carboxyl group, which is generally detrimental to the glycosidation, was instead harnessed as the key to solving the long-standing issue of α-sialidation. These results also represent the achievement of a general, substrate-controlled stereoselective glycosidation. The prominent features of our method, including complete stereoselectivity, high glycosidation yield, broad substrate scope and high applicability toward sialic acid congeners, could revolutionize the synthesis of sialoglycans. Furthermore, the bicyclic glycosyl donor strategy would streamline the chemical synthesis of Kdo-containing oligosaccharides.Innovation of the glycosidation reaction of sialic acidHiromune AndoFigure 2. Synthesis of a fluorescent labeled lacto-series ganglioside probe via the late-stage sialylation and the single molecule tracking of the fluorescent ganglioside in the PMlipopolysaccharides. References46
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