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

Carbohydr Res. 2023 Nov 25;535:108990. doi: 10.1016/j.carres.2023.108990. Online ahead of print.ABSTRACTStage-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.PMID:38039697 | DOI:10.1016/j.carres.2023.108990

Source: Carbohydrate Research - December 1, 2023 Category: Genetics & Stem Cells Authors: Rita Pal Ayano Yamazaki Naoko Komura Hide-Nori Tanaka Akihiro Imamura Hideharu Ishida Hiromune Ando Source Type: research