C-5 modifications in N-acetyl-neuraminic acid: scope and limitations.
Glycoconjugates containing sialic acid are involved in a large variety of biological phenomena, including cell-cell adhesion, recognition by viruses and bacteria, and oncogenesis. Therefore, they are important synthetic targets for the design of drugs and vaccines. In the last decades, different methodologies that improve yield and stereoselectivity in sialylation reactions have been investigated. This review summarizes the latest developments in the synthesis of C-5 modified sialic acid glycosyl donors and glycosyl acceptors and their application in the synthesis of alpha-sialosides.
De Meo
Cristina
C
Department of Chemistry, Southern Illinois University Edwardsville, Edwardsville, IL 62026, USA. cdemeo@siue.edu
Priyadarshani
Uvege
U
D001386:Azides / Q000737:chemistry; D019158:N-Acetylneuraminic Acid / Q000031:analogs & derivatives* / Q000737:chemistry*; D023303:Oxazolidinones / Q000737:chemistry; D014269:Trifluoroacetic Acid / Q000737:chemistry
D001386:Azides; D023303:Oxazolidinones; D014269:Trifluoroacetic Acid; D019158:N-Acetylneuraminic Acid