Highly selective biotransformation of arbutin to arbutin-α-glucoside using amylosucrase from Deinococcus geothermalis DSM 11300 |
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Authors: | Dong-Ho Seo Jong-Hyun Jung Suk-Jin Ha Myoung-Chong Song Jaeho Cha Sang-Ho Yoo Tae-Jip Kim Nam-In Baek Cheon-Seok Park |
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Institution: | aGraduate School of Biotechnology, and Institute of Life Science and Resources, Kyung Hee University, 1 Seocheon, Kiheung, Yongin 446-701, Republic of Korea;bDepartment of Microbiology, Pusan National University, Busan 609-735, Republic of Korea;cDepartment of Food Science and Technology, Sejong University, Seoul 143-747, Republic of Korea;dDepartment of Food Science and Technology, Chungbuk National University, Cheongju 361-763, Republic of Korea |
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Abstract: | Arbutin (Ab, 4-hydroxyphenyl β-glucopyranoside) is a glycosylated hydroquinone known to prevent the formation of melanin by inhibiting tyrosinase. An arbutin-α-glucoside was synthesized by the transglycosylation reaction of amylosucrase (AS) of Deinococcus geothermalis (DGAS) using arbutin and sucrose as an acceptor and a donor, respectively. The maximum yield of the arbutin transglycosylation product was determined to be over 98% with a 1:0.5 molar ratio of donor and acceptor molecules (sucrose and arbutin), in 50 mM sodium citrate buffer pH 7 at 35 °C. TLC and HPLC analyses revealed that only one transglycosylation product was observed, supporting the result that the transglycosylation reaction of DGAS was very specific. The arbutin transglycosylation product was isolated by preparative recycling HPLC. The structural analyses using 13C and 1H NMR proved that the transglycosylated product was 4-hydroxyphenyl β-maltoside (Ab-α-glucoside), in which a glucose molecule was linked to arbutin via an α-(1 → 4)-glycosidic linkage. |
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Keywords: | Amylosucrase Arbutin Deinococcus geothermalis Stereoselective transglycosidation |
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