Abstract
BackgroundRecently synthesized novel oligosaccharides have been produced primarily by hydrolases and glycosyltransferases, while phosphorylases have also been subject of few studies. Indeed, phosphorylases are expected to give good results via their reversible reaction. The purpose of this study was to synthesis other novel oligosaccharides using kojibiose phosphorylase.ResultsThree novel oligosaccharides were synthesized by glucosyltransfer from β-D-glucose 1-phosphate (β-D-G1P) to xylosylfructoside [O-α-D-xylopyranosyl-(1→2)-β-D-fructofuranoside] using Thermoanaerobacter brockii kojibiose phosphorylase. These oligosaccharides were isolated using carbon-Celite column chromatography and preparative high performance liquid chromatography. Gas liquid chromatography analysis of methyl derivatives, MALDI-TOF MS and NMR measurements were used for structural characterisation. The 1H and 13C NMR signals of each saccharide were assigned using 2D-NMR including COSY (correlated spectroscopy), HSQC (herteronuclear single quantum coherence), CH2-selected E-HSQC (CH2-selected Editing-HSQC), HSQC-TOCSY (HSQC-total correlation spectroscopy) and HMBC (heteronuclear multiple bond correlation).ConclusionThe structure of three synthesized saccharides were determined, and these oligosaccharides have been identified as O-α-D-glucopyranosyl-(1→2)-O-α-D-xylopyranosyl-(1→2)-β-D-fructofuranoside (saccharide 1), O-α-D-glucopyranosyl-(1→2)-O-α-D-glucopyranosyl-(1→2)-O-α-D-xylopyranosyl-(1→2)-β-D-fructofuranoside (saccharide 2) and O-α-D-glucopyranosyl-(1→[2-O-α-D-glucopyranosyl-1]2→2)-O-α-D-xylopyranosyl-(1→2)-β-D-fructofuranoside (saccharide 3).
Highlights
Synthesized novel oligosaccharides have been produced primarily by hydrolases and glycosyltransferases, while phosphorylases have been subject of few studies
Such oligosaccharides are primarily synthesized by hydrolases and glycosyltransferases
Phosphorylases have been the subject of few studies, they are expected to give good results via their reversible reaction
Summary
Synthesized novel oligosaccharides have been produced primarily by hydrolases and glycosyltransferases, while phosphorylases have been subject of few studies. The synthesis of oligosaccharides with various functions has been actively performed for some time. Such oligosaccharides are primarily synthesized by hydrolases and glycosyltransferases. Phosphorylases have been the subject of few studies, they are expected to give good results via their reversible reaction. Thermoanaerobacter brockii kojibiose phosphorylase is known to catalyze the reversible phosphorolysis of kojibiose into β-D-glucose 1-phosphate (β-D-G1P) and glucose [1]. In this reversible reaction, the enzyme uses various oligosaccharides as accepters. This enzyme is understood to catalyze glucosyltransfer from β-D-G1P to position 2 of the glucose residue in oligosaccharides such as raffinose, stachyose [2], 1-kestose, nystose [3] and sucrose
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