Lipase-catalyzed enantioselective acylation of 3-benzyloxypropane-1,2-diol in supercritical carbon dioxide

Kmecz, Ildikó; Simándi, Béla; Poppe, László; Juvancz, Zoltán; Renner, Katalin; Bódai, Viktória; Tőke, Enikő R.; Csajági, Csaba; Sawinsky, J.

doi:10.1016/j.bej.2005.11.010

Cited by 22 publications

(8 citation statements)

References 14 publications

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“…Lipases constitute the majority of enzymes employed in research involving Sc-CO 2 [62]. Kmecz et al (2006) studied the enentioselective acylation of 3-benzyloxypropane-1,2-diol in Sc-CO 2 using lipases from different sources. When compared to the reaction in mixture of hexane and tetrahydrofuran, lower yield (20-25% vs. 46%), but somewhat higher enantiomeric purity (86% ee vs. 80% ee) were detected [69].…”

Section: Supercritical Fluidsmentioning

confidence: 99%

“…Kmecz et al (2006) studied the enentioselective acylation of 3-benzyloxypropane-1,2-diol in Sc-CO 2 using lipases from different sources. When compared to the reaction in mixture of hexane and tetrahydrofuran, lower yield (20-25% vs. 46%), but somewhat higher enantiomeric purity (86% ee vs. 80% ee) were detected [69]. Romero et al (2005) studied the synthesis of isoamyl acetate from isoamyl alcohol by two different immobilized lipases (Novozym 435 from Candida antarctica and Lipozyme RM-IM from Rhizomucor miehei) using both n-hexane and Sc-CO 2 as reaction media.…”

Section: Supercritical Fluidsmentioning

confidence: 99%

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Enzymatic processes in alternative reaction media: a mini review

et al. 2015

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Biocatalysis is a growing field in the production of fine chemicals and will most probably increase its share in the future. Enzymatic reactions are carried out under mild conditions, i.e., non-toxic solvents, low temperature and pressure, which eliminates most environmental drawbacks associated with conventional production methods. The superiority of chemo-, regio-and enantioselectivity of enzymes exhibit significant advantages over conventional catalysts for production of fine chemicals, flavors, fragrances, agrochemicals and pharmaceuticals. Enzymes can function both in aqueous and non-aqueous solvents. As a result of the growing scientific and industrial interest towards green chemistry, green solvent systems, which are mainly water, supercritical fluids, ionic liquids, fluorinated solvents, and solvent-free systems have become more popular in biocatalysis. However, the activity and selectivity of an enzyme is heavily dependent on solvent properties. In this review, various green solvents were classified and some of their influential features on enzyme activity were discussed.

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Section: Supercritical Fluidsmentioning

confidence: 99%

Section: Supercritical Fluidsmentioning

confidence: 99%

Enzymatic processes in alternative reaction media: a mini review

et al. 2015

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“…Since July 2002, Thomas Swan & Co. Ltd. have been operating a 800 t/a test facility to perform heterogeneously catalyzed reactions in supercritical carbon dioxide [22][23][24]. Carbon dioxide (usually, with the addition of water) is particularly suited for enzyme-catalyzed reactions as it does not attack the enzymes (latest examples: [25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44], see also [45]). The enzymes are usually insoluble or immobilized.…”

Section: Chemical Reactions In Supercritical Carbon Dioxidementioning

confidence: 99%

Heterogeneous Catalysis in Supercritical Media: 1. Carbon Dioxide

Kruse

Vogel

2007

Chem Eng & Technol

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Dedicated to Prof. Dr.-Ing. Jens Weitkamp on the occasion of his 65th birthdayOver the past few years, supercritical fluids have received considerable interest as reaction media. Supercritical fluids combine properties of gases and liquids. Densities are lower than in the liquid phase, but significantly higher than in the gas phase. This makes supercritical fluids excellent solvents for a variety of substances. The good dissolution capacity exists only in or near the supercritical range. Reaction products can be separated, for instance, simply by decreasing temperature and pressure. This may be used to intensify the process as complex separation processes, like distillation, are avoided.

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“…Introduction of an oxygen heteroatom into the cyclopropane ring resulted in reduced yields for all of the above fungal lipases. Another interesting environment for determination of biocatalytic activity was described by Kmecz et al who employed supercritical carbon dioxide [82] and determined the ability of a range of thermophilic lipases from fungi such as Thermoascus thermophilus and Talaromyces emersonii to acetylate 3benzyloxypropane-1,2-diol 84. (9) have reported kinetic resolution using a solid state environment where there is 60-70 % moisture.…”

Section: Activity Of Lipases Derived From Fungal Sourcesmentioning

confidence: 99%

The Current Chemical Utility of Marine and Terrestrial Filamentous Fungi in Side-Chain Chemistry

Hunter¹

2007

COC

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This review focuses on three aspects of the application of marine and terrestrial filamentous fungi to side-chain chemistry from 2000 to early 2006. The first section covers the generation of novel biologically active side-chain containing metabolites. This includes a range of antibiotic, cytotoxic and novel bioactive compounds. The second section discusses the use of these fungi both whole cell and lipases of fungal origin in the chemical modification of side-chains. Examples include reductive desymmetrization of pro-chiral ketones, dynamic kinetic resolution and unique reactions. The final section details the degradation of side-chains by fungi and includes lignin and steroid transformations for determination metabolism and the generation of new skeletal structure.

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Lipase-catalyzed enantioselective acylation of 3-benzyloxypropane-1,2-diol in supercritical carbon dioxide

Cited by 22 publications

References 14 publications

Enzymatic processes in alternative reaction media: a mini review

Enzymatic processes in alternative reaction media: a mini review

Heterogeneous Catalysis in Supercritical Media: 1. Carbon Dioxide

The Current Chemical Utility of Marine and Terrestrial Filamentous Fungi in Side-Chain Chemistry

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