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Various oligosaccharides obtained by the hydrolysis of chitin, a β-(1,4)-linked polymer of N-acetyl-D-glucosamine (2-acetamide2-deoxy-D-glucopyranose, GlcNAc), exhibit preventative effects against celiac disease, which is caused by gliadin-derived peptides.1 It was also confirmed that several disaccharides, consisting of D-galactopyranose (Gal) and GlcNAc, showed physiologically beneficial functions,2,3 which indicate that these chitin oligosaccharides are promising candidates as pharmaceuticals. Based on the hypothesis that other GlcNAccontaining oligosaccharides could also exhibit physiologically beneficial functions, our group has engaged in the production of various oligosaccharides, such as β-D-fructofuranosyl-(2→1)-βD-fructofuranosyl-(2↔1)-2-acetamido-2-deoxy-α-D-glucopyranoside4 and β-D-fructofuranosyl α-D-galactopyranosyl-(1→6)-2acetamido-2-deoxy-α-D-glucopyranoside.5 To accumulate the physicochemical and biochemical properties of various types of functional oligosaccharides, a novel oligosaccharide was synthesized from β-D-fructofuranosyl-(2↔1)-2-acetamido-2deoxy-α-D-glucopyranoside (SucNAc) and lactose (Lac) via transgalactosylation catalyzed by β-galactosidase [EC 3.2.1.23] of Aspergillus oryzae.6 Herein, we report on the X-ray crystal structure of β-D-galactopyranosyl-(1→6)-β-D-fructofuranosyl(2↔1)-2-acetamido-2-deoxy-α-D-glucopyranoside (1), which is a novel trisaccharide comprised of D-galactose, N-acetyl-Dglucosamine and D-fructose (Fig. 1). The crystal structure was compared with the solution structure using NMR spectroscopy. A colorless block crystal of 1, having approximate dimensions of 0.20 × 0.20 × 0.20 mm, was mounted in a loop. Data was collected at 138 K on a Rigaku R-AXIS RAPID imaging plate area detector with graphite-monochromated Mo Kα radiation. The structure was solved by direct methods and refined on F2 using all of the reflections. All of the nonhydrogen atoms were refined using the anisotropic atomic displacement parameters, and hydrogen atoms were inserted at the calculated positions using a riding model. The parameters for data collection and refinement are summarized in Table 1, and the crystal structure of 1 is shown in Fig. 2. C6 and its adjacent oxygen atoms of Gal (Fig. 1) were disordered. Both atoms, corresponding to C20/C21 and O16/O17 in Fig. 2, were determined to have 0.676:0.324 abundance. In the determination of four water molecules, one water molecule comprising O18 was refined including hydrogen atoms; the remaining three water molecules, O19/O22, O20/O23 and O21/O24, were disordered (Fig. 2). All disordered water molecules were determined to have 0.726:0.274 abundance. The distance between H5′ of GlcNAc and H4′′ of Fru was 2.63 Å in the crystal structure, and the corresponding NOE signal was observed by NMR spectroscopy (Fig. 3). These results indicated that the conformation of the GlcNAc-Fru moiety in the crystal structure was similar to that in the solution structure. The dihedral angles of 1 and sucrose (refcode 2017 © The Japan Society for Analytical Chemistry

Crystal Structure of β-D-Galactopyranosyl-(1→6)-β-D-fructofuranosyl-(2↔1)-2-acetamido-2-deoxy-α-D-glucopyranoside