Enzymatic synthesis of salicin glycosides through transglycosylation catalyzed by amylosucrases from Deinococcus geothermalis and Neisseria polysaccharea |
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Authors: | Jong-Hyun Jung Dong-Ho Seo Suk-Jin Ha Myoung-Chong Song Jaeho Cha Sang-Ho Yoo Tae-Jip Kim Nam-In Baek Moo-Yeol Baik Cheon-Seok Park |
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Institution: | aGraduate School of Biotechnology, and Institute of Life Science and Resources, Kyung Hee University, 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: | Amylosucrase (ASase, EC 2.4.1.4) is a member of family 13 of the glycoside hydrolases that catalyze the synthesis of an α-(1→4)-linked glucan polymer from sucrose instead of an expensive activated sugar, such as ADP- or UDP-glucose. Transglycosylation reactions mediated by the ASases of Deinococcus geothermalis (DGAS) and Neisseria polysaccharea (NPAS) were applied to the synthesis of salicin glycosides with sucrose serving as the glucopyranosyl donor and salicin as the acceptor molecule. Two salicin glycoside transfer products were detected by TLC and HPLC analyses. The synthesis of salicin glycosides was very efficient with NPAS with a yield of over 90%. In contrast, DGAS specifically synthesized only one salicin transglycosylation product. The transglycosylation products were identified as α-d-glucopyranosyl-(1→4)-salicin (glucosyl salicin) and α-d-glucopyranosyl-(1→4)-α-d-glucopyranosyl-(1→4)-salicin (maltosyl salicin) by NMR analysis. The ratio between donor and acceptor had a significant effect on the type of product that resulted from the transglycosylation reaction. With more acceptors present in the reaction, more glucosyl salicin and less maltosyl salicin were synthesized. |
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Keywords: | Amylosucrase Deinococcus geothermalis Glucosyl-salicin Maltosyl-salicin Salicin Transglycosylation |
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