Lirdprapamongkol K, Svasti J (2000) Alkyl glucoside synthesis using Thai rosewood β-glucosidase. Lang M, Kamrat T, Nidetzky B (2006) Influence of ionic liquid cosolvent on transgalactosylation reactions catalyzed by thermostable β-glycosylhydrolase CelB from Pyrococcus furiosus. Kongsaeree PT, Ratananikom K, Choengpanya K, Tongtubtim N, Sujiwattanarat P, Porncharoennop C, Onpium A, Svasti J (2010) Substrate specificity in hydrolysis and transglucosylation by family 1 β-glucosidases from cassava and Thai rosewood. Kim Y-M, Kim B-H, Ahn J-S, Kim G-E, Jin S-D, Nguyen T-H, Kim D (2009) Enzymatic synthesis of alkyl glucosides using Leuconostoc mesenteroides dextransucrase. Ketudat Cairns JR, Esen A (2010) β-Glucosidases. Kaftzik N, Wasserscheid P, Kragl U (2002) Use of ionic liquids to increase the yield and enzyme stability in the β-galactosidase catalyzed synthesis of N-acetyllactosamine. Can J Chem 80:653–656įerrières V, Bertho J-N, Plusquellec D (1998) A convenient synthesis of alkyl D-glycofuranosiduronic acids and alkyl D-glycofuranosides from unprotected carbohydrates. Enzyme Microb Technol 29:513–520ĭucret A, Carrière J-F, Trani M, Lortie R (2002) Enzymatic synthesis of octyl glucoside catalyzed by almond β-glucosidase in organic media. Biotechnol Prog 17:881–886ĭe Roode BM, van Beek J, van der Padt A, Franssen MCR, Boom RM (2001b) The integrated enzymatic production and downstream processing of hexyl glucoside. Proc Natl Acad Sci USA 97:13555–13560ĭe Roode BM, Oliehoek L, van der Padt A, Franssen MCR, Boom RM (2001a) Downstream processing of enzymatically produced geranyl glucoside. J Nanosci Nanotechnol 19:1172–1175Ĭzjzek M, Cicek M, Zamboni V, Bevan DR, Henrissat B, Esen A (2000) The mechanism of substrate (aglycone) specificity in β-glucosidases is revealed by crystal structures of mutant maize β-glucosidase-DIMBOA, -DIMBOAGlc, and -dhurrin complexes. J Chem Eng Data 52:2166–2170Ĭhung KH, Kim H, Park Y-K, Kim B-H, Kim S-J, Jung S-C (2019) Decyl glucoside synthesized by direct glucosidation of D-glucose over zeolite catalysts and its estrogenicity as non-endocrine disruptive surfactant. Wiley, Weinheim, pp 3–24Īlves LA, Almeida e Silva JB, Giulietti M (2007) Solubility of D-glucose in water and ethanol/water mixtures. In: Carrea G, Riva S (eds) Organic synthesis with enzymes in non-aqueous media. Carbohydr Res 314:177–187Īdlercreutz P (2008) Fundamentals of biocatalysis in neat organic solvents. The N189F dalcochinase mutant and the non-aqueous reaction systems described here show great potential for future commercial production of long-chain alkyl glucosides.Īdasch V, Hoffmann B, Milius W, Platz G, Voss G (1998) Preparation of alkyl α- and β-D-glucopyranosides, thermotropic properties and X-ray analysis. This is the first report of enzymatic synthesis of OG and DG via reverse hydrolysis reactions in ionic liquids and co-solvent mixtures. The identities of OG and DG products were confirmed by HRMS and NMR. On the other hand, the highest yield of DG (64 mol%) was obtained in the reaction containing 0.5 M glucose, 3 unit ml −1 enzyme in 20% (v/v) decanol, 20% (v/v) acetone and 50% (v/v) at 30 ☌. The highest yield of OG (67 mol%) was obtained in the reaction containing 0.5 M glucose, 3 unit ml −1 enzyme in 20% (v/v) octanol and 70% (v/v) at 30 ☌. To synthesize octyl β- d-glucopyranoside (OG) and decyl β- d-glucopyranoside (DG) in three non-aqueous reaction systems, namely organic solvents, ionic liquids and co-solvent mixtures, via reverse hydrolysis reactions catalyzed by the N189F dalcochinase mutant.
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