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Abstract <p>α-Glucosylglycerol (αGG), an α-glucoside found in alcoholic beverages, exhibits beneficial physiological effects. However, high costs and low yields limit its availability in the market. Therefore, we aimed to optimize the conditions for high-yield αGG production and establish a method for effective αGG separation. Accordingly, maltose and glycerol were used as the α-glucosyl donor and acceptor, respectively. Enzymatic production was executed using XgtA, an α-glucosidase derived from <i>Xanthomonas campestris</i> WU-9701, and glucose isomerase (GI). The products were αGG comprising 1-<i>O</i>-αGG and 2-<i>O</i>-αGG. αGG was separated from the reaction solution using activated carbon, followed by high-performance liquid chromatography (HPLC) and liquid chromatography–mass spectrometry. Under optimal conditions, the concentrations of αGG and 1-<i>O</i>-αGG reached 1141 mM and 1072 mM, respectively, within 48 h. These are the highest values obtained by enzymatic production to date. 1-<i>O</i>-αGG and 2-<i>O</i>-αGG were separated using an HPLC system equipped with the DCpak PMPC column. The area ratio of the two separated peaks of the products was 94:6 for the enzymatic reaction solution containing 1141 mM αGG. The products corresponding to these peaks were isolated for nuclear magnetic resonance analysis. The main product was confirmed to be 1-<i>O</i>-αGG, whereas the other was 2-<i>O</i>-αGG. Furthermore, the melting point of 1-<i>O</i>-αGG was 126 °C. Finally, the enzymatic products were confirmed to be 1-<i>R</i>-<i>O</i>-αGG, 1-<i>S</i>–<i>O</i>-αGG, and 2-<i>O</i>-αGG. These findings confirmed the successful high-yield and enzymatic production of αGG, and the first isolation and chemical identification of 1-<i>O</i>-αGG. Our method can potentially be implemented in industrial processes, owing to its high productivity.</p> Key points <p>• <i>We enzymatically produced the highest 1-O-α-GG yield reported to date</i></p> <p>• <i>We developed methods for 1-O-αGG and 2-O-αGG detection and characterization</i></p> <p>• <i>The 1-O-αGG:2-O-αGG ratio changed according to the reaction temperature</i></p>

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High-yield production of α-glucosylglycerol using Xanthomonas campestris WU-9701 derived XgtA

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  • 发表日期：

    2026年5月28日

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  • Kanon Suzuki,
  • Yoshitaka Ishii,
  • Kohtaro Kirimura

摘要

Abstract

α-Glucosylglycerol (αGG), an α-glucoside found in alcoholic beverages, exhibits beneficial physiological effects. However, high costs and low yields limit its availability in the market. Therefore, we aimed to optimize the conditions for high-yield αGG production and establish a method for effective αGG separation. Accordingly, maltose and glycerol were used as the α-glucosyl donor and acceptor, respectively. Enzymatic production was executed using XgtA, an α-glucosidase derived from Xanthomonas campestris WU-9701, and glucose isomerase (GI). The products were αGG comprising 1-O-αGG and 2-O-αGG. αGG was separated from the reaction solution using activated carbon, followed by high-performance liquid chromatography (HPLC) and liquid chromatography–mass spectrometry. Under optimal conditions, the concentrations of αGG and 1-O-αGG reached 1141 mM and 1072 mM, respectively, within 48 h. These are the highest values obtained by enzymatic production to date. 1-O-αGG and 2-O-αGG were separated using an HPLC system equipped with the DCpak PMPC column. The area ratio of the two separated peaks of the products was 94:6 for the enzymatic reaction solution containing 1141 mM αGG. The products corresponding to these peaks were isolated for nuclear magnetic resonance analysis. The main product was confirmed to be 1-O-αGG, whereas the other was 2-O-αGG. Furthermore, the melting point of 1-O-αGG was 126 °C. Finally, the enzymatic products were confirmed to be 1-R-O-αGG, 1-S–O-αGG, and 2-O-αGG. These findings confirmed the successful high-yield and enzymatic production of αGG, and the first isolation and chemical identification of 1-O-αGG. Our method can potentially be implemented in industrial processes, owing to its high productivity.

Key points

• We enzymatically produced the highest 1-O-α-GG yield reported to date

• We developed methods for 1-O-αGG and 2-O-αGG detection and characterization

• The 1-O-αGG:2-O-αGG ratio changed according to the reaction temperature