Diastereocontrolled Synthesis of Carbon Glycosides of N-Acetylneuraminic Acid via Glycosyl Samarium(III) Intermediates

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Vlahov, I.R.
Vlahov, P.I.
Linhardt, Robert J.
Issue Date
1997
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Article
Language
ENG
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Biology , Chemistry and chemical biology , Chemical and biological engineering , Biomedical engineering
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Abstract
α-O-Glycosides of N-acetylneuraminic acid (Neu5Ac, 1, Scheme 1) are often found terminating the oligosaccharide component of cell-surface glycoproteins and glycolipids. Neu5Ac is involved in a number of important biological events:  intercellular interactions such as adhesion, aggregation, and agglutination; masking of antigenic oligosaccharides and suppressing undesired immune reactions (antirecognition phenomena); influencing the cell membrane permeability for ions, amino acids, and proteins; and protection of glycoproteins against proteolysis. 1 Terminal Neu5Ac is an attachment site of pathogens to the cells, and often catabolic and inflammatory processes are initiated on the removal of this carbohydrate group. 2 In general the “right” life time of a cell is a reflection of a delicate balance between the introduction and removal of terminal Neu5Ac or other sialic acids.
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Journal of the American Chemical Society, 119, 1480-1481
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Diastereocontrolled Synthesis of Carbon Glycosides of N-AcetylneuraminicAcid via Glycosyl Samarium(III) Intermediates, I. R. Vlahov, P. I. Vlahov,R.J. Linhardt, Journal of the American Chemical Society, 119,1480-1481, 1997.
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