Enzymatic synthesis and the structure elucidation of novel trisaccharides comprised of D-galactose,N-acetyl-D-glucosamine,and D-fructose |
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| Authors: | Mitsuru Tashiro Takashi Fujimoto Kazuo Furihata Yohei Sakaki Takako Hirano Wataru Hakamata |
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| Affiliation: | 1. Department of Chemistry, College of Science and Technology, Meisei University, Hino, Tokyo, Japantashiro@chem.meisei-u.ac.jp;3. Department of Chemistry, College of Science and Technology, Meisei University, Hino, Tokyo, Japan;4. Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, University of Tokyo, Bunkyo-ku, Tokyo, Japan;5. Department of Chemistry and Life Science, College of Bioresource Sciences, Nihon University, Fujisawa, Kanagawa, Japan |
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| Abstract: | 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. |
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| Keywords: | β-galactosidase oligosaccharide structural analysis transgalactosylation |
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