Synthesis of 9-O-acetyl- and 4,9-di-O-acetyl derivatives of the methyl ester of N-acetyl-beta-D-neuraminic acid methylglycoside. Their use as models in periodate oxidation studies.
Reaction of the methyl ester of N-acetyl-beta-D-neuraminic acid methyl glycoside with N-acetylimidazole yielded the corresponding 9-O-acetyl- and 4,9-di-O-acetyl derivatives. The structures of these compounds were confirmed by mass spectrometry and both 1H and 13C NMR spectroscopy. The compounds served as model substances in a comparative study of the rate of periodate oxidation of unsubstituted and of 9-O-acetylated-N-acetyl-neuraminic acids. This reaction was strongly hampered by the presence of the 9-O-acetyl group. The low molar absorbancy coefficient of N-acetyl-9-O-acetylneuraminic acid in the periodic acid/thiobarbituric acid assay can be explained by this retardation.
D055598:Chemical Phenomena; D002621:Chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008759:Methylglycosides / Q000138:chemical synthesis*; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D010504:Periodic Acid; D012794:Sialic Acids; D013329:Structure-Activity Relationship
D008759:Methylglycosides; D012794:Sialic Acids; D010504:Periodic Acid