title: Synthesis of partially O-acetylated N-acetylneuraminic acid using regioselective silyl exchange technology.
abstract: Postglycosylation acetylation of sialic acid imparts unique roles to sialoglycoconjugates in mammalian immune response making structural and functional understanding of these analogues important. Five partially O-acetylated Neu5Ac analogues have been synthesized. Reaction of per-O-silylated Neu5Ac ester with AcOH and Ac2O in pyridine promotes regioselective silyl ether/acetate exchange in the following order: C4 (2°) > C9 (1°) > C8 (2°) > C2 (anomeric). Subsequent hydrogenolysis affords the corresponding sialic acid analogues as useful chemical biology tools.
authors.affiliation: Department of Chemistry, University of California, Davis , One Shields Avenue, Davis, California 95616, United States.
authors.forename: Simon S
authors.initials: SS
authors.lastname: Park
authors.forename: Jacquelyn
authors.initials: J
authors.lastname: Gervay-Hague
mesh_terms: D000107:Acetylation; D000818:Animals; D015394:Molecular Structure; D019158:N-Acetylneuraminic Acid / Q000138:chemical synthesis* / Q000737:chemistry; D012794:Sialic Acids / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D012794:Sialic Acids; D019158:N-Acetylneuraminic Acid