Enzymatic synthesis and the structure elucidation of novel trisaccharides comprised of D-galactose, N-acetyl-D-glucosamine, and D-fructose

摘要

Enzymatic synthesis of trisaccharides from N-acetylsucrosamine and lactose utilizing the transgalactosylation activity of Aspergillus oryzae β-galactosidase provided two reaction products. Structure analyses by various 2D NMR spectroscopy and MS indicated that the products were β-D-fructofuranosyl β-D-galactopyranosyl-(1→6)-2-acetamido-2-deoxy-α-D-glucopyranoside and β-D-galactopyranosyl-(1→6)-β-D-fructofuranosyl-(2←→1)-2-acetamido-2-deoxy-α-D-glucopyranoside. Moreover, J-resolved-HMBC experiments indicated that the conformations around the glycosidic bonds of these trisaccharides were very similar. Examination about the pH and thermal stabilities of the glycosidic bonds in the GlcNAc-Fru moiety of the two trisaccharides indicated apparent difference.