Convergent synthesis of functionalized derivatives of stage-specific embryonic antigens 3 & 4.

Autor: Pal R; Institute for Glyco-core Research (iGCORE), Gifu University, 1-1 Yanagido, Gifu, 501-1193, Japan; Institute for Integrated Cell-Material Sciences, Kyoto University, Kyoto, 606-8501, Japan., Yamazaki A; Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu, 501-1193, Japan., Komura N; Institute for Glyco-core Research (iGCORE), Gifu University, 1-1 Yanagido, Gifu, 501-1193, Japan; Institute for Integrated Cell-Material Sciences, Kyoto University, Kyoto, 606-8501, Japan. Electronic address: komura.naoko.a1@f.gifu-u.ac.jp., Tanaka HN; Institute for Glyco-core Research (iGCORE), Gifu University, 1-1 Yanagido, Gifu, 501-1193, Japan., Imamura A; Institute for Glyco-core Research (iGCORE), Gifu University, 1-1 Yanagido, Gifu, 501-1193, Japan; Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu, 501-1193, Japan., Ishida H; Institute for Glyco-core Research (iGCORE), Gifu University, 1-1 Yanagido, Gifu, 501-1193, Japan; Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu, 501-1193, Japan., Ando H; Institute for Glyco-core Research (iGCORE), Gifu University, 1-1 Yanagido, Gifu, 501-1193, Japan; Institute for Integrated Cell-Material Sciences, Kyoto University, Kyoto, 606-8501, Japan. Electronic address: ando.hiromune.i0@f.gifu-u.ac.jp.
Jazyk: angličtina
Zdroj: Carbohydrate research [Carbohydr Res] 2024 Jan; Vol. 535, pp. 108990. Date of Electronic Publication: 2023 Nov 25.
DOI: 10.1016/j.carres.2023.108990
Abstrakt: Stage-specific embryonic antigens (SSEAs) are carbohydrate markers that have diverse roles in embryonic development. However, the exact roles of SSEAs remain unclear. To obtain mechanistic insights into their roles, we aimed to develop functionalized SSEA glycan analogs via chemical synthesis. Herein, we report a convergent synthetic approach for SSEA-3 and SSEA-4 analogs using readily available versatile building blocks. A key step, namely the stereoselective glycosylation of a common tetrasaccharide acceptor, was successfully achieved using a 4-O-Bn Gal donor for SSEA-3 and a Neu-Gal donor for SSEA-4, which were previously developed by our group. The obtained SSEA-3 and SSEA-4 glycans were further functionalized with biotin and deuterated lipid for applications in biological studies. Thus, the findings of this study will facilitate further research on SSEAs.
Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
(Copyright © 2023 Elsevier Ltd. All rights reserved.)
Databáze: MEDLINE
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