Being
considered greener alternatives to ionic liquids (IL), deep
eutectic solvents (DES) and natural deep eutectic solvents (NADES)
have currently attracted broad interests from academics and industry.
In this study, the transformation of isoeugenol to vanillin catalyzed
by Lysinibacillus fusiformis CGMCC1347 cells was
taken as the model reaction to examine the impacts of 24 DESs and
21 NADESs as cosolvents on whole-cell biocatalysis. Both types of
cosolvents showed the ability of improving the production yields up
to 142% and 132% of the ones obtained in (NA)DES-free aqueous systems,
respectively. The data obtained by confocal laser scanning microscopy
and flow cytometry tests and measurements of OD260 and OD280 agreed
well with the bioconversion data, suggesting that addition of these
cosolvents may be beneficial to whole-cell biocatalysis in enhancing
the cellular membrane permeability. Interaction of DES with bacterial
cell wall was discussed. The cells immobilized in PVA-alginate beads
granted an augmented production yield in the presence of DES and NADES,
up to 181% of the one obtained in a pure water system, and their catalytic
activity was well maintained after being used for at least 13 cycles.
As nonionic surfactants derived from naturally renewable resources such as sugars and fatty acids, sugar fatty acid esters have been widely utilized in food, cosmetic and pharmaceutical industries. Our present study has demonstrated that the inexpensive and halogen-free tetraalkylammonium salts (e.g., [Bu 4 N][Ac], [Et 4 N][Ac] and [Me 4 N][Ac]) can act as dual solvents-catalysts for regioselective acylation to produce glucose laurate. This non-enzymatic synthesis can proceed under mild conditions with high specificity, and the conversions obtained were superior to that when an enzyme catalyst (lipase, EC 3.1.1.3) was added. A higher yield was obtained in the ammonium salt with a longer alkyl chain on the cation, while no product was obtained in [Bu 4 N][HSO 4 ] and [Bu 4 P][Ac]. A reaction mechanism has been proposed, which is supported by phase-transfer catalysis and law of matching water affinity.
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