Synthesis of p-methoxyphenyl sulfated β-GalNAc derivatives with inhibitory activity against Japanese encephalitis virus

Abstract

Abstract The N-acetylgalactosamine (GalNAc) residue is one of the units of chondroitin sulfate E (CS-E) which has been reported to have inhibitory activity against Japanese encephalitis virus (JEV). Herein, we describe the synthesis of a series of p-methoxyphenyl β-GalNAc derivatives with a sulfate group at 3-, 4-, and/or 6-positions using an efficient route through a common synthetic intermediate. By measuring the inhibition activity of these compounds that bear different numbers and positions of sulfate groups, the effect of position specificity for interaction with the virus was determined. From these results, GalNAc6S and GalNAc4S6S derivatives inhibited JEV infections well; we suggest the 6-O-sulfate group is necessary for selective recognition by the virus.