Kinetic and enantioselective behavior of the lipase from Candida cylindracea: A comparative study between the soluble enzyme and the enzyme immobilized on agarose and silica gels

Sánchez, Eva M.; Bello, J. F.; Roig, Manuel G.; Burguillo, F.J.; Moreno, Juan A.; Sinisterra, J. V.

doi:10.1016/0141-0229(95)00133-6

Cited by 20 publications

(5 citation statements)

References 29 publications

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“…This enhancement of enantioselectivity may be explained by the increased rigidity of the enzyme conformation due to interactions with the polymer. Similar phenomena have been described for the lipase from Candida cylindracea immobilized on agarose and silica gel (44).…”

Section: Enzyme-catalyzed Hydrolysis Of 3-acetylthiohexanalsupporting

confidence: 79%

Stereoselectivity of the Generation of 3-Mercaptohexanal and 3-Mercaptohexanol by Lipase-Catalyzed Hydrolysis of 3-Acetylthioesters

Wakabayashi

Eisenreich

et al. 2003

J. Agric. Food Chem.

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The enantioselectivity of the generation of 3-mercaptohexanal and 3-mercaptohexanol, two potent sulfur-containing aroma compounds, by lipase-catalyzed hydrolysis of the corresponding 3-acetylthioesters was investigated. The stereochemical course of the kinetic resolutions was followed by capillary gas chromatography using modified cyclodextrins as chiral stationary phases. The enzyme preparations tested varied significantly in terms of activity and enantioselectivity (E). The highest E value (E = 36) was observed for the hydrolysis of 3-acetylthiohexanal catalyzed by lipase B from Candida antarctica resulting in (S)-configured thiol products. Immobilization of the enzyme (E = 85) and the use of tert-butyl alcohol as cosolvent (E = 49) improved the enantioselectivity. Modification of the acyl moiety of the substrate (3-benzoylthiohexanal) had no significant impact. The sulfur-containing compounds investigated possess attractive odor properties, and only one of the enantiomers exhibits the pleasant citrus type note.

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Section: Enzyme-catalyzed Hydrolysis Of 3-acetylthiohexanalsupporting

confidence: 79%

Stereoselectivity of the Generation of 3-Mercaptohexanal and 3-Mercaptohexanol by Lipase-Catalyzed Hydrolysis of 3-Acetylthioesters

Wakabayashi

Eisenreich

et al. 2003

J. Agric. Food Chem.

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“…The former had approximately seven times greater enantioselectivity than the soluble enzyme whereas CLR immobilized on agarose activated with tosylate had only four times the selectivity of the native enzyme [210]. The former had approximately seven times greater enantioselectivity than the soluble enzyme whereas CLR immobilized on agarose activated with tosylate had only four times the selectivity of the native enzyme [210].…”

Section: Factors Affecting Enzyme Performancementioning

confidence: 95%

“…It was found that CRL immobilized on silica activated with 2,4,6-trichloro-1,3,5-triazine was approximately seven times more enantioselective than the soluble enzyme, whereas CLR immobilized on agarose activated with tosylate was only four times more selective than the native enzyme [210]. Sanchez and co-workers studied the enantioselectivity of CRL covalently immobilized on agarose and silica activated with tosylate and triazine, respectively.…”

Section: Conformation-controlled Enantioselectivitymentioning

confidence: 99%

Covalent Enzyme Immobilization

Cao¹

2005

Carrier‐bound Immobilized Enzymes

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“…This review, however, focuses on lipase (acyglycerol hydrolases EC 3.1.1.3) only, which plays an important role in the synthesis processes of hydrolysis, esterification, and transesterification. Of all the lipase available, Candida cylindracea (also known as Candida rugosa) has been given particular attention as an ideal catalyst for the resolution of racemic esters and alcohols [8][9][10][11][15][16][17].…”

Section: Role Of Enzyme In Synthesismentioning

confidence: 99%

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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Kinetic and enantioselective behavior of the lipase from Candida cylindracea: A comparative study between the soluble enzyme and the enzyme immobilized on agarose and silica gels

Cited by 20 publications

References 29 publications

Stereoselectivity of the Generation of 3-Mercaptohexanal and 3-Mercaptohexanol by Lipase-Catalyzed Hydrolysis of 3-Acetylthioesters

Stereoselectivity of the Generation of 3-Mercaptohexanal and 3-Mercaptohexanol by Lipase-Catalyzed Hydrolysis of 3-Acetylthioesters

Covalent Enzyme Immobilization

Enzymatic Membrane Reactor for Chiral Drugs Synthesis

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