Neuraminic acid chemistry

Sugar derivatives that contain double bonds have been developed and used so extensively that they almost certainly constitute the most versatile category of carbohydrate compounds available for use in synthesis. They may be applied both in the synthesis of complex members of the family and of a myriad enantiomerically pure noncarbohydrate compounds—notably, many of interest in medicinal chemistry. Furthermore, some unsaturated sugar derivatives have themselves been found to possess important therapeutic properties. For example, the unnatural L-nucleoside 1 inhibits reverse transcriptase and shows potent and selective anti-AIDS activity,1 and the unsaturated neuraminic acid analogue 2 is the sialidase-inhibitory... 

Neuraminic acid and its Structures, Chemistry, Biological Activity ARMANDODORIANO BIANCO AND CRISTIANA MELCHIONI 103... 

NEURAMINIC ACID - STRUCTURE, CHEMISTRY, BIOLOGICAL ACTIVITY... 

The chemistry of neuraminic acid and derivatives has been reviewed by Zilliken and Whitehouse184 and by GottschalK.185... 

CHEMISTRY AND ANTIVIRAL ACTIVITY Zanamivir (4-guanidino-2,4-dideoxy-2, 3-dehydro-/V-acetyl neuraminic acid) is a siaMc acid analog that potently and specifically inhibits the neuraminidases of influenza A and B viruses. Depending on the strain, zanamivir competitively inhibits influenza neuraminidase activity but affects neuraminidases from other pathogens and mammalian sources only at much higher concentrations. Zanamivir inhibits in vitro replication of influenza A and B viruses, including amantadine- and rimantadine-resistant strains and several oseltamivir-resistant variants. 

Klenk E. On the discovery and chemistry of neuraminic acid and gangjiosides. Chem Phys Lipids. 1970 5(1) 193-197. van Echten-Deckert G, Walter J. Sphingolipids critical players in Alzheimer s disease. Prog Lipid Res. 2012 51(4) 378-393. 

Klenk, E., 1958a, Neuraminic acid, in Chemistry and Biology of Micropolysaccharides (G. E. W. Wolstenholme and M. O Connor, eds.), pp. 296-305, Little Brown, Boston. 

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