Influence of OR ester group length on the catalytic activity and enantioselectivity of free lipase and immobilized in membrane used for the kinetic resolution of naproxen esters

Giorno, Lidietta; D’Amore, E.; Drioli, Enrico; Cassano, Roberta; Picci, Nevio

doi:10.1016/j.jcat.2007.01.021

Cited by 22 publications

(11 citation statements)

References 6 publications

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“…The enantioselectivity ( E ) was calculated from the enantiomeric excess of the product ( ee p , %) at a certain conversion ( c , %) based on the following equations …”

Section: Methodsmentioning

confidence: 99%

Lipase‐catalyzed hydrolysis of (+,‐)‐2‐(4‐methylphenyl) propionic methyl ester enhanced by hydroxypropyl‐β‐cyclodextrin

Liu

Zhang

et al. 2018

J of Chemical Tech & Biotech

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BACKGROUND Enzymatic kinetic resolution is an attractive technology for production of enantiomerically pure compounds. The objective of this research is to investigate the enantioselective hydrolysis of (+,‐)‐2‐(4‐methylphenyl) propionic methyl ester (2‐(4‐MP)PPAME) to (+)‐2‐(4‐methylphenyl) propionic acid ((+)‐2‐(4‐MP)PPA) catalyzed by enzyme in an aqueous medium. RESULTS Lipase AY from candida rugosa (CRL) was screened as the best lipase. Novozym 435 IM and lipopan S BG show higher catalytic activity but the enantioselectivity is very low. By addition of hydroxypropyl‐β‐cyclodextrin (HP‐β‐CD) to the aqueous system, an increased substrate conversion of 45.28% was obtained, the high enantiomeric excess remaining compared with the conversion of 28.05% without HP‐β‐CD. Response surface methodology and central composite design were employed to model and optimize the reaction system. CONCLUSION Under the optimal conditions including pH of 6.60, 12.5 mg mL−1 enzyme, 35 mmol L−1 HP‐β‐CD, 0.06 mmol substrate, temperature 39°C, agitation speed 400 rpm and 40 h reaction time, the substrate conversion was up to 40.32% and the optical purity of the product (+)‐2‐(4‐methylphenyl) propionic acid was up to 95.22%. © 2018 Society of Chemical Industry

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“…The enantioselectivity ( E ) was calculated from the enantiomeric excess of the product ( ee p , %) at a certain conversion ( c , %) based on the following equations …”

Section: Methodsmentioning

confidence: 99%

Lipase‐catalyzed hydrolysis of (+,‐)‐2‐(4‐methylphenyl) propionic methyl ester enhanced by hydroxypropyl‐β‐cyclodextrin

Liu

Zhang

et al. 2018

J of Chemical Tech & Biotech

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“…As for lipase-immobilized membrane bioreactors, they are usually used in the field of non-aqueous phase catalysis such as synthesis (74)(75)(76)(77)(78)(79), hydrolysis (80)(81)(82) and kinetic resolution of compounds (83)(84)(85)(86)(87)(88)(89). For example, Tan et al fabricated a lipase-immobilized membrane bioreactor for synthesis of 2-ethylhexyl palmitate, obtaining an average esterification degree of 95% and a product purity of 98% (77).…”

Section: Potential Applications In Bioreactorsmentioning

confidence: 99%

Polymer materials for enzyme immobilization and their application in bioreactors

Fang¹,

Huang²,

Chen³

et al. 2011

BMB Reports

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Enzymatic catalysis has been pursued extensively in a wide range of important chemical processes for their unparalleled selectivity and mild reaction conditions. However, enzymes are usually costly and easy to inactivate in their free forms. Immobilization is the key to optimizing the in-service performance of an enzyme in industrial processes, particularly in the field of non-aqueous phase catalysis. Since the immobilization process for enzymes will inevitably result in some loss of activity, improving the activity retention of the immobilized enzyme is critical. To some extent, the performance of an immobilized enzyme is mainly governed by the supports used for immobilization, thus it is important to fully understand the properties of supporting materials and immobilization processes. In recent years, there has been growing concern in using polymeric materials as supports for their good mechanical and easily adjustable properties. Furthermore, a great many work has been done in order to improve the activity retention and stabilities of immobilized enzymes. Some introduce a spacer arm onto the support surface to improve the enzyme mobility. The support surface is also modified towards biocompatibility to reduce non-biospecific interactions between the enzyme and support. Besides, natural materials can be used directly as supporting materials owning to their inert and biocompatible properties. This review is focused on recent advances in using polymeric materials as hosts for lipase immobilization by two different methods, surface attachment and encapsulation. Polymeric materials of different forms, such as particles, membranes and nanofibers, are discussed in detail. The prospective applications of immobilized enzymes, especially the enzyme-immobilized membrane bioreactors (EMBR) are also discussed. [BMB reports 2011; 44(2): 87-95]

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“…Performance of the hydrolysis in terms of activity and enantioselectivity is increased with decrease of aliphatic chains of the alcohol group. 72,73 During these processes, the enzyme acts as an enantioselective converting system and the HFM functions as a barrier that separates the enantiomers, 33,43 as illustrated in Fig. 4.…”

Section: Application Of Tsp-emr: Immobilized Enzymes Resolution Of Ramentioning

confidence: 99%

“…77 Production of (S)-naproxen acid obtained excellent product enantiomeric excess (74-100%), but low conversion values (<10%). 21,52,60,65,72 Candida rugosa lipase (CRL) immobilized on sponge layers of polyamide membranes was operated to hydrolyse the substrate, (R, S)-naproxen ester, dissolved in isooctane at 30…”

Section: Drugs and Intermediatesmentioning

confidence: 99%

“…Compared with the batch stirred tank free-enzyme reaction, the enzymatic reactor exhibited higher activity per mass of protein. 65,72 Initially, a high concentration of racemic naproxen methyl ester was resolved by CCL in a polyacrylonitrile multiphase TSP-EMR at high flow rates on both phases. 40 For 36 hs, the hydrolytic rates were 9-14 µmol h −1 .…”

Section: Drugs and Intermediatesmentioning

confidence: 99%

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Enzymatic membrane reactors: the determining factors in two separate phase operations

Agustian¹,

Kamaruddin²,

Bhatia³

2011

J of Chemical Tech & Biotech

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A two separate phase-enzymatic membrane reactor is an attractive process since it has a large interfacial area and exchange surfaces, simultaneous reaction and separation and other benefits. Many factors influence its successful operation, and these include characteristics of the enzyme, membrane, circulating fluids and reactor operations. Although the operating conditions are the main factor, other factors must be considered before, during or after its application. At the initial stage of reactor development, the solubility of substrates and products, type of operation, membrane material and size, enzyme preparation and loading procedure, and cleanliness of the recirculated fluids should be specified. The immobilization site, reactor arrangement, dissolved or no-solvent operation, classic or emulsion operation and immobilized or suspended enzyme(s) are determined later. Some factors still need further studies. Utilization of the technology is described for use from multigram-to plant-scale capacity to process racemic and achiral compounds. The racemates were resolved primarily by kinetic resolution, but dynamic kinetic resolution has been exploited. The technology focused on hydrolytic reactions, but esterification processes were also exploited.

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Influence of OR ester group length on the catalytic activity and enantioselectivity of free lipase and immobilized in membrane used for the kinetic resolution of naproxen esters

Cited by 22 publications

References 6 publications

Lipase‐catalyzed hydrolysis of (+,‐)‐2‐(4‐methylphenyl) propionic methyl ester enhanced by hydroxypropyl‐β‐cyclodextrin

Lipase‐catalyzed hydrolysis of (+,‐)‐2‐(4‐methylphenyl) propionic methyl ester enhanced by hydroxypropyl‐β‐cyclodextrin

Polymer materials for enzyme immobilization and their application in bioreactors

Enzymatic membrane reactors: the determining factors in two separate phase operations

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