Lipase-catalyzed acylation in a continuous down-flow fixed-bed reactor

Enhanced Electroreduction of Acetophenone Using Lipase Stabilization: Improved Conversion to 1‐Phenylethanol

“…Given this, it is proposed that the performance of the different lipases involved in electroreduction may also be related to the effect of the substrate itself on the catalytic potential of the enzyme. There is evidence that the exposure of Candida antarctica B lipase (Novozym 435) to an acetophenone solution (0.02 mol L −1 ) decreased the formation of the desired product by 17 % in that study, which the authors classified as a slight inhibition of enzyme activity [53] . In contrast, tests involving the subjection of porcine pancreatic lipases, such as type II, to an acetophenone solution (8×10 −3 mol L −1 ) revealed a 33 % inhibition of enzymatic activity, considered relevant [54]…”

“…There is evidence that the exposure of Candida antarctica B lipase (Novozym 435) to an acetophenone solution (0.02 mol L À 1 ) decreased the formation of the desired product by 17 % in that study, which the authors classified as a slight inhibition of enzyme activity. [53] In contrast, tests involving the subjection of porcine pancreatic lipases, such as type II, to an acetophenone solution (8 × 10 À 3 mol L À 1 ) revealed a 33 % inhibition of enzymatic activity, considered relevant. [54] Therefore, some lipases are more affected by acetophenone (1) in the medium, while others are less affected.…”

One-pot synthesis of (R)-2-acetoxy-1-indanone from 1,2-indanedione combining metal catalyzed hydrogenation and chemoenzymatic dynamic kinetic resolution

“…35,[92][93][94][95][96] Furthermore, some of these heterogeneously catalyzed DKR reactions have been converted into flow type reaction applications. [46][47][48] In the literature, the reported one-pot catalyst systems suffer, however, from often reduced catalytic activities. The racemization catalysts may be inhibited to various degrees by the starting materials or products.…”

“…Thus, mutually compatible tailored catalyst combinations are required, not undergoing severe catalyst inactivation or poisoning pathways induced by the reaction products, starting materials or intermediates. Ideally, this type of heterogeneous reaction sequences could also further be converted to flow type systems, [46][47][48] receiving increasing interest both in industry and academic laboratories in recent years. [49][50][51][52][53][54] In the present paper, we describe our work on the combination of the two earlier published reactions by us, namely, the regioselective hydrogenation of 1,2-indanedione 9 and the chemoenzymatic dynamic kinetic resolution of rac-2 (ref.…”

Neat lipase-catalysed kinetic resolution of racemic 1-phenylethanol and a straightforward modelling of the reaction

“…Lipase-catalysed esterification of 1-phenylethanol is one of the best known model reaction of the kinetic resolution of secondary alcohols (Zhou et al 2011;Overmeyer et al 1999;Chua and Sarmidi 2004;Chua et al 2010). Although, most commonly used esterification agent is vinyl-acetate, other acyl-donors can be applied efficiently as well (Li et al 2013;Paiva et al 2011;Teixeira and Lourenço 2014;Sahin et al 2012). Although vinyl esters have the advantage to shift the equilibrium towards ester formation, due to the oxo-enol tautomerisation of the coproduct formed (Wang et al 1988), vinyl acetate is a highly volatile non-renewable.…”