Optimization and kinetic modeling of lipase catalyzed enantioselective N-acetylation of ( ± )-1-phenylethylamine under microwave irradiation

Abstract

BACKGROUND: Optically pure amines are used in the fine chemical industry as resolving agents, chiral auxiliaries, and chiral synthetic building blocks for pharmaceuticals as well as agrochemicals. Lipase-catalyzed kinetic resolution of (±)-1-phenylethylamine with ethyl acetate as an acyl donor was achieved using immobilized lipase (Novozyme 435) as a biocatalyst under microwave irradiation.

Kinetics and optimization of lipase-catalyzed synthesis of rose fragrance 2-phenylethyl acetate through transesterification

“…After that, the interaction of carboxylic-lipase with 2-PE, forming another binary complex, subsequently releases the product 2-PEAc and lipase. The rate equation for the ping-pong bi-bi mechanism with inhibition by 2-PE [32], is as follows: (5) where is the initial reaction rate, V max is the maximum initial reaction rate and K VAc and K 2-PE are the binding constants for vinyl acetate and 2-phenylethanol, respectively. K i2-PE is the 2-PE inhibition constant.…”

“…This proximity leads to the formation of the product (2-PEAc and vinyl alcohol) and their subsequent release. The rate equation for the order bi-bi mechanism [32] is as follows:…”

Kinetics and mechanism of regioselective monoacetylation of 3-aryloxy-1,2-propandiols using immobilized Candida antarctica lipase

“…Higher yield of enantioselective product is obtained in final 37 step when pure monoacetylated product is used as substrate. 38 Lipases are the most important group of biocatalysts in non-39 aqueous enzymology; they do not need cofactors for assisting the 40 reaction, are capable of differentiating the chiral centers and have 41 extensive substrate specificity [23][24][25][26][27][28][29][30][31][32]. Lipases are widely 42 present in different sources which include bacteria and fungi 43 and hence can be readily available for biotransformation of 44 interest.…”

Microwave assisted process intensification of lipase catalyzed transesterification of 1,2 propanediol with dimethyl carbonate for the green synthesis of propylene carbonate: Novelties of kinetics and mechanism of consecutive reactions

“…For instance, the effect of microwave irradiated lipase-catalyzed reactions has earlier been tried out to witness rate enhancement [29][30][31][32][33][34][35][36][37]. It has been found that Microwave irradiation has practically no effect on activation energy or has only moderate effect in a few cases, but it provides enough excitation to overcome the energy barrier.…”

“…The two important factors have significant contribution on effect of microwave in enzyme catalysts: (i) di-electric property, and (ii) polarity of reaction medium. Microwave irradiation also assists in improving thermal stability of the enzyme [30,31] as a function of enzyme hydration which increases selectivity and leads to a better process [32]. Enzyme catalyzed consecutive reactions have not been modelled adequately and the kinetic information is lacking [39].…”