Selection of Pure Enantiomers of 1-Phenyl Alcohols by Sequenced Processes of Ester Hydrolysis and Transesterification in Enzyme Membrane Reactors

Ceynowa, Józef; Koter, Izabela

doi:10.1081/ss-100100797

Cited by 6 publications

(2 citation statements)

References 13 publications

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“…In the operation of flat membrane reactor, there are cases where soluble enzyme is suspended in the reaction medium composed only of organic solvent, and it is simply named as single-phase reaction. Rosell [22], Giorno [18,23,24,25], Ceynowa [26,27,28] and their co-workers have used the EMR for reactions involving aqueous and organic phases for both fine chemicals and fatty acids production. In multiphase membrane reactor, two types of membrane are being used, namely hydrophilic and hydrophobic membrane.…”

Section: Reaction Media In Emrmentioning

confidence: 99%

“…It was reported that the productivity of a hollowfiber membrane reactor was more stable than that of the flat sheet enzyme membrane reactor. The use of a high recirculation ratio of substrate feed rate through the capillary fibers to the entire system, was reported to allow the system to be modeled as a continuous-flow stirred-tank reactor (CSTR), as shown in Figure 5 [27]. The recycle CSTR membrane system was more flexible as the reaction and the separation zones were physically separated.…”

Section: Synthesis Of A-arylpropionic Acids (Nsaids)mentioning

confidence: 99%

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Enzymatic Membrane Reactor for Chiral Drugs Synthesis

Wei¹,

Harun@Kamaruddin²,

Bhatia³

2012

Jurnal Teknologi

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Kepentingan kekiralan dalam aktiviti farmaseutikal telah menuntut kaedah yang berproduktif tinggi dan ekonomik untuk mensintesis enantiomer tulen secara komersil. Ubat moden kerap mengunakan enantiomer daripada suatu campuran stereo–isomer. Permintaan terhadap agen terapeutik yang tulen secara optik menjadi semakin kritikal kerana cirinya yang lebih spesifik berbanding campuran rasemik. Walau bagaimanapun, teknologi konvesional yang dipraktikkan selama ini menghasilkan campuran kedua-dua enantiomer yang sukar dipisahkan. Dalam konteks ini, resolusi berenzim ialah suatu cara untuk mengatasi masalah ini. Resolusi kinetik ialah suatu kaedah yang membolehkan pecahan substratum baki dihasilkan dengan ketulenan enantiomer yang tinggi. Secara unggul, satu daripada enantiomer bertindak balas secara enantiopilihan dengan kadar yang lebih cepat bagi suatu entiti kiral. Sebagai suatu teknologi yang berpotensi tinggi dalam penghasilan enantiomer spesifik, reaktor membran berenzim (EMR) berjaya mengatasi kekurangan yang dialami oleh sistem konvensional. Reaktor membran berenzim menggabungkan pengangkutan jisim memilih dengan tindak balas kimia, dan penyingkiran memilih produk daripada medium tindak balas. Ciri unggul yang ditunjukkan oleh reaktor membran berenzim ialah keupayaannya meningkatkan penghasilan tindak balas berenzim yang berbentuk perencat produk atau tindak balas yang tak sesuai secara termodinamik. Berbanding lipase lain yang ada, lipase daripada Candida rugosa dianggap sebagai suatu biomangkin yang unggul bagi resolusi campuran ester dan alkohol, kerana lipase ini bertindak secara enantiopilihan dan memangkin pensistesisan enantiomer melalui tindak balas hidrolisis. Dalam kertas kerja ini, penggunaan sistem EMR lipase tak boleh gerak terhadap perkembangan teknologi kiral dibincangkan secara umum, dengan tumpuan khusus diberikan terhadap penghasilan drug kiral. Kata kunci: Drug kiral; ketulenan secara optik; enantiomer; resolusi kinetik; reaktor membran berenzim The increasing popularity of chirality in pharmaceutical activity has stimulated an increasing demand for economical and high productive methods for commercial synthesis of pure enantiomers. Modern medicines often call for just one enantiomer of a stereo–isomer. The demand for these optically pure therapeutic agents is becoming more stringent due to its more–specific characteristic than racemic mixtures. However, conventional technologies yield a mixture of both isomers which are difficult to separate. In this context, enzymatic resolution is a subject of recent investigation, where high efficiency of heterogeneous and homogeneous catalyzed multiphase chemistries is being explored. Kinetic resolution is a method in which the residual substrate fraction can be obtained in high enantiomeric purity. Ideally one enantiomer reacts faster than the other with a chiral entity. As a potential technology for the production of specific enantiomer, enzymatic membrane reactor (EMR) has been reported to overcome some of the limitations of the conventional system. Enzymatic membrane reactors combine selective mass transport with chemical reactions, and the selective removal of products from the reaction site increases the conversion of product–inhibited or thermodynamically unfavorable reactions. Of all the lipase available, lipase from Cadida rugosa is given particular attention as an ideal biocatalyst for the resolution of racemic esters and alcohols, as it acts enantioselectively and prefers to catalyze the synthesis of one of the enantiomers using hydrolysis with higher preference. In this paper, the authors presented a review of unique potential application of lipase–immobilized EMR systems towards the development of chirotechnology that has been presented which mainly focuses on chiral drugs production. Key words: Chiral drugs, optical purity; enantiomers; kinetic resolution; enzymatic membrane reactors

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Section: Reaction Media In Emrmentioning

confidence: 99%

Section: Synthesis Of A-arylpropionic Acids (Nsaids)mentioning

confidence: 99%

Enzymatic Membrane Reactor for Chiral Drugs Synthesis

Wei¹,

Harun@Kamaruddin²,

Bhatia³

2012

Jurnal Teknologi

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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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Immobilization of Candida rugosa lipase on polypropylene microfiltration membrane modified by glycopolymer: hydrolysis of olive oil in biphasic bioreactor

Deng

Dai

et al. 2005

Enzyme and Microbial Technology

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Selection of Pure Enantiomers of 1-Phenyl Alcohols by Sequenced Processes of Ester Hydrolysis and Transesterification in Enzyme Membrane Reactors

Cited by 6 publications

References 13 publications

Enzymatic Membrane Reactor for Chiral Drugs Synthesis

Enzymatic Membrane Reactor for Chiral Drugs Synthesis

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

Immobilization of Candida rugosa lipase on polypropylene microfiltration membrane modified by glycopolymer: hydrolysis of olive oil in biphasic bioreactor

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