A highly efficient diastereoselective synthesis of alpha-isosalicin by maltase from Saccharomyces cerevisiae
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Jankov, Ratko M.
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In this report, alpha-isosalicin, a potent anticoagulant and skin whitening agent, was synthesized by a highly efficient chemoselective and diastereoselective reaction, catalyzed by maltase from bakers' yeast (Saccharomyces cerevisiae). The highest yield of this one-step transglucosylation reaction was achieved with 50 mM of salicyl alcohol as a glucose acceptor. The key reaction factors were optimized using response surface methodology (RSM) with an enzyme concentration of 10 U/mL. The optimum temperature of the reaction was determined as 36.5 degrees C, the optimal maltose concentration was 40% (w/v), the optimal pH was 6.5, and the optimal reaction time was 16 h. Under these conditions 75% of alpha-isosalicin was obtained, with a yield of 10 g/L, and no by product formation was observed.
Keywords:alpha-Isosalicin / Glucosidase / Salicyl alcohol / Transglucosylation / Bakers' yeast
Source:Process Biochemistry, 2011, 46, 8, 1698-1702
- Elsevier Sci Ltd, Oxford
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