Synthesis of anomeric ethyl ketosides of 5-N-acetyl-D-neuraminic acid.
The syntheses of anomeric ethyl ketosides of 5-N-acetyl-D-neuraminic acid are described. The alpha-anomer prepared by a modified Koenigs-Knorr procedure starting from acetochloroneuraminic acid is quantitatively cleaved by Vibrio cholerae neuraminidase. Proton-catalyzed reaction of 5-N-acetyl-D-neuraminic acid with ethanol yields the beta-anomer.
D055598:Chemical Phenomena; D002621:Chemistry; D007536:Isomerism; D008722:Methods; D009439:Neuraminidase / Q000378:metabolism; D012794:Sialic Acids; D013329:Structure-Activity Relationship; D014734:Vibrio cholerae / Q000201:enzymology
D012794:Sialic Acids; D009439:Neuraminidase