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KMID : 0545120190290040562
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Journal of Microbiology and Biotechnology
2019 Volume.29 No. 4 p.562 ~ p.570
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Enzymatic Synthesis of β-Glucosylglycerol and Its Unnatural Glycosides Via β-Glycosidase and Amylosucrase
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Jung Dong-Hyun
Seo Dong-Ho
Park Ji-Hae
Kim Myo-Jung
Baek Nam-In
Park Cheon-Seok
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Abstract
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β-Glucosylglycerol (β-GG) and their derivatives have potential applications in food, cosmetics and the healthcare industry, including antitumor medications. In this study, β-GG and its unnatural glycosides were synthesized through the transglycosylation of two enzymes, Sulfolobus shibatae β-glycosidase (SSG) and Deinococcus geothermalis amylosucrase (DGAS). SSG catalyzed a transglycosylation reaction with glycerol as an acceptor and cellobiose as a donor to produce 56% of β-GGs [β-D-glucopyranosyl-(1→1/3)-D-glycerol and β-D-glucopyranosyl- (1→2)-D-glycerol]. In the second transglycosylation reaction, β-D-glucopyranosyl-(1 → 1/3)-Dglycerol was used as acceptor molecules of the DGAS reaction. As a result, 61% of α-Dglucopyranosyl-( 1→4)-β-D-glucopyranosyl-(1→1/3)-D-glycerol and 28% of α-D-maltopyranosyl- (1→4)-β-D-glucopyranosyl-(1→1/3)-D-glycerol were synthesized as unnatural glucosylglycerols. In conclusion, the combined enzymatic synthesis of the unnatural glycosides of β-GG was established. The synthesis of these unnatural glycosides may provide an opportunity to discover new applications in the biotechnological industry.
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KEYWORD
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Glycerol glycosides, β-glycosidase, amylosucrase, transglycosylation
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