Abstract:Abstract:The applicability of deep eutectic solvents has been demonstrated for the first time in promiscuous lipase-catalysed aldol reactions. The model reaction between 4-nitrobenzaldehyde and acetone was examined in depth, an excellent compatibility being found between porcine pancreas lipase and choline chloride: glycerol mixtures for the formation of the aldol product in high yields. The system was compatible with a series of aromatic aldehydes and ketones including acetone, cyclopentanone and cyclohexanon… Show more
“…The recyclability experiment performed on DES and enzyme for four cycles depicted a continuous decrease in the activity after every reuse. This is the first report of the lipase catalysed aldol reaction in deep eutectic solvents …”
Lipase-catalyzed organic reactions have widely been practiced in the past three decades. In addition to its wide acceptance in conventional reactions such as hydrolysis, transesterification, and enantiopure synthesis (kinetic resolution and dynamic kinetic resolution) several reports on the catalytic promiscuity of lipases have also been published. The concept of promiscuity, where lipase catalyzes reactions beyond its natural function, has been perceived as a useful phenomenon which can enhance the utility of lipase as a biocatalyst. Many useful organic reactions such as Aldol condensation, Hantzsch reaction, Canizzaro reaction, Mannich reaction, Baylis-Hillman reaction, Knoevenagel condensation, Michael addition, Ugi reaction, and oxidation catalyzed by lipases have surfaced in the literature. The current review is a critical compilation of such research findings to put forth the synthetic applications of lipase, beyond the orthodox biocatalytic toolbox.
“…The recyclability experiment performed on DES and enzyme for four cycles depicted a continuous decrease in the activity after every reuse. This is the first report of the lipase catalysed aldol reaction in deep eutectic solvents …”
Lipase-catalyzed organic reactions have widely been practiced in the past three decades. In addition to its wide acceptance in conventional reactions such as hydrolysis, transesterification, and enantiopure synthesis (kinetic resolution and dynamic kinetic resolution) several reports on the catalytic promiscuity of lipases have also been published. The concept of promiscuity, where lipase catalyzes reactions beyond its natural function, has been perceived as a useful phenomenon which can enhance the utility of lipase as a biocatalyst. Many useful organic reactions such as Aldol condensation, Hantzsch reaction, Canizzaro reaction, Mannich reaction, Baylis-Hillman reaction, Knoevenagel condensation, Michael addition, Ugi reaction, and oxidation catalyzed by lipases have surfaced in the literature. The current review is a critical compilation of such research findings to put forth the synthetic applications of lipase, beyond the orthodox biocatalytic toolbox.
“…Thus, lipases are used in vitro to catalyze reactions different from those of the natural hydrolase function, [49][50][51][52][53][54] such as esterification, [55][56][57][58][59][60][61] acidolysis, [62][63][64][65][66][67] interesterificaton, [68][69][70][71] transesterification, [72][73][74][75][76] aminolysis, [77][78][79][80][81] perhydrolysis, 82,83 etc., together with a collection of the so-called promiscuous reactions. [84][85][86][87][88][89][90][91][92] Lipases are usually quite stable, and so they have been used in diverse media, like aqueous media, organic solvents, [93][94][95] ionic liquids, [96]…”
“…Gonzalez-Martinez and co-workers investigated the lipase-catalyzed aldol reactions in DES-containing system in 2016 (Gonzalez-Martinez et al 2016). A model reaction between 4-nitrobenzaldehyde and acetone was set up to examine the feasibility of DES as a reaction medium for the promiscuous aldol process (Fig.…”
Section: The Application Of Dess In Biocatalysismentioning
confidence: 99%
“…The idea of trying lipase-catalyzed promiscuous reaction is of great significance to discover new functions for enzymes in DESs and synthesize many valuable chemicals.Fig. 6Lipase-catalyzed promiscuous reactions in DESs(adapted from ( a ) Gonzalez-Martinez et al 2016; ( b ) Tian et al 2016)
…”
Section: The Application Of Dess In Biocatalysismentioning
Deep eutectic solvents (DESs) are eutectic mixtures of salts and hydrogen bond donors with melting points low enough to be used as solvents. DESs have proved to be a good alternative to traditional organic solvents and ionic liquids (ILs) in many biocatalytic processes. Apart from the benign characteristics similar to those of ILs (e.g., low volatility, low inflammability and low melting point), DESs have their unique merits of easy preparation and low cost owing to their renewable and available raw materials. To better apply such solvents in green and sustainable chemistry, this review firstly describes some basic properties, mainly the toxicity and biodegradability of DESs. Secondly, it presents several valuable applications of DES as solvent/co-solvent in biocatalytic reactions, such as lipase-catalyzed transesterification and ester hydrolysis reactions. The roles, serving as extractive reagent for an enzymatic product and pretreatment solvent of enzymatic biomass hydrolysis, are also discussed. Further understanding how DESs affect biocatalytic reaction will facilitate the design of novel solvents and contribute to the discovery of new reactions in these solvents.
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