Studies on glycan processing inhibitors

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1. The 2-beta-SNa derivative of N-acetylneuraminic acid (Neu5Ac) was combined with cytidine, deoxycytidine and arabinosyl,cytosine, respectively, through the spacer-arms such as (a) -SCH_2O- and (b) -SCH_2CONH-, to give the corresponding CMP-Neu5Ac derivatives and analogs. These compounds showed the inhibition activity against Neu5Ac synthase and Neu5Ac transferase, and might be useful to analyze the biological functions of cell-surface sialo-glycoconjugates. The 2-beta-SNa derivative of 2-keto-3-deoxy-octonic acid (KDO) has, also been synthesized and combined with cytidine, deoxycytidine and arabinosyl cytosine, respectively, as described for Neu5Ac. The biological activities are now in investigation.2.1-Deoxynojirimycin (DNJ) was converted, via the epoxide intermediates, into a series of N-acetylhexosamine analogs, i. e., 2-acetamido-1,2,5-trideoxy-1,5-imino- D-glucitol (GlcNAcDNJ), -D-mannitol (ManNAcDNJ), -D-galactitol (GalNAcDNJ) and their isomers. The inhibition activity against the corresponding N-acetylhexosaminidase was examines. GlcNAcDNJ was further converted to the disaccharides related to lactose, lactosamine and chitobiose which are the prominent components of widespread glycoconjugates. More complex glycans containing DNJ as a reducing-end component will be designed.