Effective one-pot multienzyme (OPME) synthesis of monotreme milk oligosaccharides and other sialosides containing 4-O-acetyl sialic acid

Abstract

A facile one-pot two-enzyme chemoenzymatic approach has been established for the gram (Neu4,5Ac₂α3Lac, 1.33 g) and preparative scale (Neu4,5Ac₂α3LNnT) synthesis of monotreme milk oligosaccharides. Other O-acetyl-5-N-acetylneuraminic acid (Neu4,5Ac₂)- or 4-O-acetyl-5-N-glycolylneuraminic acid (Neu4Ac5Gc) -containing α2-3-sialosides have also been synthesized in the preparative scale. Used as an effective probe, Neu4,5Ac₂α3GalβpNP was found to be a suitable substrate by human influenza A viruses but not bacterial sialidases.