A highly efficient diastereoselective synthesis of alpha-isosalicin by maltase from Saccharomyces cerevisiae
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2011
Authors
Veličković, DušanDimitrijević, Aleksandra
Bihelović, Filip
Bezbradica, Dejan
Jankov, Ratko M.
Milosavić, Nenad
Article (Published version)
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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' yeastSource:
Process Biochemistry, 2011, 46, 8, 1698-1702Publisher:
- Elsevier Sci Ltd, Oxford
Funding / projects:
- Allergens, antibodies, enzymes and small physiologically important molecules: design, structure, function and relevance (RS-MESTD-Basic Research (BR or ON)-172049)
- Novel encapsulation and enzyme technologies for designing of new biocatalysts and biologically active compounds targeting enhancement of food quality, safety and competitiveness (RS-MESTD-Integrated and Interdisciplinary Research (IIR or III)-46010)
DOI: 10.1016/j.procbio.2011.05.007
ISSN: 1359-5113
WoS: 000293438300025
Scopus: 2-s2.0-79959922337
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Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Veličković, Dušan AU - Dimitrijević, Aleksandra AU - Bihelović, Filip AU - Bezbradica, Dejan AU - Jankov, Ratko M. AU - Milosavić, Nenad PY - 2011 UR - https://cherry.chem.bg.ac.rs/handle/123456789/1186 AB - 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. PB - Elsevier Sci Ltd, Oxford T2 - Process Biochemistry T1 - A highly efficient diastereoselective synthesis of alpha-isosalicin by maltase from Saccharomyces cerevisiae VL - 46 IS - 8 SP - 1698 EP - 1702 DO - 10.1016/j.procbio.2011.05.007 ER -
@article{ author = "Veličković, Dušan and Dimitrijević, Aleksandra and Bihelović, Filip and Bezbradica, Dejan and Jankov, Ratko M. and Milosavić, Nenad", year = "2011", abstract = "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.", publisher = "Elsevier Sci Ltd, Oxford", journal = "Process Biochemistry", title = "A highly efficient diastereoselective synthesis of alpha-isosalicin by maltase from Saccharomyces cerevisiae", volume = "46", number = "8", pages = "1698-1702", doi = "10.1016/j.procbio.2011.05.007" }
Veličković, D., Dimitrijević, A., Bihelović, F., Bezbradica, D., Jankov, R. M.,& Milosavić, N.. (2011). A highly efficient diastereoselective synthesis of alpha-isosalicin by maltase from Saccharomyces cerevisiae. in Process Biochemistry Elsevier Sci Ltd, Oxford., 46(8), 1698-1702. https://doi.org/10.1016/j.procbio.2011.05.007
Veličković D, Dimitrijević A, Bihelović F, Bezbradica D, Jankov RM, Milosavić N. A highly efficient diastereoselective synthesis of alpha-isosalicin by maltase from Saccharomyces cerevisiae. in Process Biochemistry. 2011;46(8):1698-1702. doi:10.1016/j.procbio.2011.05.007 .
Veličković, Dušan, Dimitrijević, Aleksandra, Bihelović, Filip, Bezbradica, Dejan, Jankov, Ratko M., Milosavić, Nenad, "A highly efficient diastereoselective synthesis of alpha-isosalicin by maltase from Saccharomyces cerevisiae" in Process Biochemistry, 46, no. 8 (2011):1698-1702, https://doi.org/10.1016/j.procbio.2011.05.007 . .