Biology; Chemistry and chemical biology; Chemical and biological engineering; Biomedical engineering
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Synthesis of nor-C-linked neuraminic acid disaccharide: A versatile precursor of C-analogs of oligosialic acids and gangliosides, X. Yuan, D. K. Ress, R. J. Linhardt, Journal of Organic Chemistry, 72, 3085-3088, 2007.
The Neu5Acalpha(2,8)Neu5Ac disaccharide is an important constituent of tumor related antigen, however, the O-linkage is catabolically unstable. Vaccination with a catabolically stable sialic acid C-glycoside analog might enhance immunogenicity. The synthesis of Neu5Ac nor-C-disaccharide 20R/S, corresponding to versatile precursors of C-analogs of oligosialic acid and gangliosides, is reported. The synthesis of the protected acceptor was not straightforward, as ester, silyl ether, and isopropylidene protection failed to afford desired C-linked disaccharide. Allyl ether protection of hydroxyl groups and acetyl protection of the acetamido facilitated the successful synthesis of the 8-aldehyde neuraminyl acceptor. Samarium mediated C-glycosylation afforded the desired nor-C-disaccharide as a mixture of two separable diastereomers.;
Journal of Organic Chemistry, 72, 3085-3088; Note : if this item contains full text it may be a preprint, author manuscript, or a Gold OA copy that permits redistribution with a license such as CC BY. The final version is available through the publisher’s platform.
The Linhardt Research Labs.; The Shirley Ann Jackson, Ph.D. Center for Biotechnology and Interdisciplinary Studies (CBIS);
American Chemical Society (ACS)
The Linhardt Research Labs Online Collection; Rensselaer Polytechnic Institute, Troy, NY; Journal of Organic Chemistry; https://harc.rpi.edu/;