869550-10-7

Upstream product

• 3587-60-8 Benzyloxymethyl chloride 
• 132591-12-9 methyl (2-C-allyl-5-N-acetamido-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranitol)onate 

Downstream Products

• 934390-47-3 dimethyl 2-(5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-(benzyloxymethyl)-1-O-(tert-butyl(dimethyl)silyl)-3,5-dideoxy-D-erythro-L-gluco-nonitol-2-C-yl)-1-((phenoxythiocarbonyl)oxyethyl)phosphonate 
• 869550-14-1 dimethyl 2-(5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-(benzyloxymethyl)-1-O-(tert-butyl(dimethyl)silyl)-3,5-dideoxy-D-erythro-L-gluco-nonitol-2-C-yl)ethylphosphonate 
• 869550-12-9 5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-(benzyloxymethyl)-1-O-(tert-butyl(dimethyl)silyl)-3,5-dideoxy-2-C-(2-propenyl)-D-erythro-L-gluco-nonitol 
• 869550-13-0 6-acetamido-3,7-anhydro-5,8,9,10-tetra-O-(benzyloxymethyl)-3-C-((tert-butyl(dimethyl)silyl)oxymethyl)-2,4,6-trideoxy-D-erythro-L-manno-decose 
• 869550-11-8 5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-(benzyloxymethyl)-3,5-dideoxy-2-C-(2-propenyl)-D-erythro-L-gluco-nonitol 

Relevant academic research and scientific papers

Synthesis of bisubstrate and donor analogues of sialyltransferase and their inhibitory activities

Sialyltransferases (STs) are involved in the biosynthesis of glycoconjugates with important biological activities. Most STs utilize cytidine-5′-monophospho-N-acetylneuraminic acid (CMP-Neu5Ac) as a common donor substrate. A bisubstrate analogue containing the donor substrate (CMP-Neu5Ac mimic) and the acceptor substrate (galactose) was synthesized. Four donor analogues having the partial structure of the bisubstrate analogue were also synthesized to support study of the structure-activity relationship. Each analogue contains an ethylene group in place of the exocyclic anomeric oxygen of CMP-Neu5Ac. The bisubstrate analogue exhibited only weak inhibitory activity to rat recombinant α-2,3- and α-2,6-ST (IC50 = 1.3, 2.4 mM). Conversion of the C-1 carboxylate of the Neu5Ac moiety to carboxyamide, hydroxymethyl, or methylene phosphate each resulted in a reduction in inhibitory activity. Among the synthesized analogues, cytidin-5′-yl sialylethylphosphonate (4) was the most potent inhibitor against rat recombinant α-2,3- and α-2,6-ST (IC50 = 0.047, 0.34 mM).