Enantioselective esterification of ibuprofen in supercritical carbon dioxide by immobilized lipase

Rantakylä, Markku; Aaltonen, Olli

doi:10.1007/bf00133961

Cited by 48 publications

(27 citation statements)

References 10 publications

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“…They attributed the pressure effect to changes of the reactants' partitioning between the supercritical fluid and the vicinity of the enzyme. Likewise, Rantakylä and Aaltonen [39] reported a decrease of reaction rate with rising pressure in the enantioselective esterification of racemic ibuprofen with 1-propanol catalyzed by Lipozyme IM 20.…”

Section: Effect Of Pressurementioning

confidence: 94%

“…Steytler et al [37] presented the esterification of lauric acid with butanol catalyzed by supported Candida lipase with a conversion of about 20% within 3 h. Here again, the quantity of enzyme used is very high with 2.4 g in a reactor volume of 120 mL. Furthermore, comparing to other studies [38,39] concerning lipase-catalyzed reactions in scCO 2 , it seems that one of the main advantages of MBGs is the very small quantity of enzyme required for the efficient catalysis of such reactions (here, 1.20 mg).…”

Section: Choice Of Systemmentioning

confidence: 95%

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Biocatalysis using lipase encapsulated in microemulsion-based organogels in supercritical carbon dioxide

Blattner

Zoumpanioti

Kröner

et al. 2006

The Journal of Supercritical Fluids

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Lipases from Candida antarctica and Mucor miehei were encapsulated in lecithin water-in-oil (w/o) microemulsion-based organogels (MBG). These gels were formulated with either hydroxypropylmethyl cellulose (HPMC) or gelatin. The esterification of lauric acid and 1-propanol catalyzed by these MBGs was examined in supercritical carbon dioxide (scCO 2 ; 35• C, 110 bar) as solvent for the substrates. The results were compared to those obtained with the reference substrate solvent isooctane. It turned out that the initial rates of this model reaction in scCO 2 were higher than those observed in the reference system. Various parameters affecting the biocatalysis such as pressure, alcohol and acid chain length, and gel composition were investigated. Kinetic studies showed that the ester synthesis catalyzed by the immobilized C. antarctica lipase occurs via a Ping Pong Bi Bi mechanism in which only inhibition by excess of alcohol was identified. Values of all kinetic parameters were determined. In addition, experiments on the reusability of these gels in scCO 2 were carried out and the state of water within the organogel was examined with the help of differential scanning calorimetry. The present study shows that biocatalysis using MBGs in scCO 2 is a promising alternative to other bioconversion processes.

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Section: Effect Of Pressurementioning

confidence: 94%

Section: Choice Of Systemmentioning

confidence: 95%

Biocatalysis using lipase encapsulated in microemulsion-based organogels in supercritical carbon dioxide

Blattner

Zoumpanioti

Kröner

et al. 2006

The Journal of Supercritical Fluids

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“…In enzymecatalysed reactions, increasing temperature generally decreases selectivity. [52][53][54][55][56][57][58][59][60][61][62] In a few studies, however, enhanced selectivity with increasing temperature, 63,64 or a maximum of enantioselectivity at a certain temperature, 38,65 or even indifference to temperature was found. 66 In most of the quoted examples, the enzyme-catalysed reactions were carried out in batch mode (in stirred or shaken flasks) and only a few studies on the temperature effects on lipase-catalysed KRs were performed in continuous-flow mode so far.…”

Section: Introductionmentioning

confidence: 99%

Lipase-Catalyzed Kinetic Resolution of 1-(2-Hydroxycyclohexyl)Indoles in Batch and Continuous-Flow Systems

et al. 2014

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The lipase catalysed kinetic resolution of three trans-1-(2-hydroxycyclohexyl)-indoles in both batch and continuous-flow systems is reported. Ring opening of cyclohexene oxide by the corresponding indole followed by enzymatic acylation with vinyl acetate resulted in novel, highly enantioenriched indole-substituted cyclohexanols and cyclohexyl acetates. The effect of the temperature on enantiomeric ratio (E) and productivity (specific reaction rate, r flow ) in the continuous-flow mode acylation was studied at analytical scale in the 0-70°C range.Preparative scale kinetic resolution of the three indole derivatives was performed in mixed continuous-and recirculation-flow mode resulting in almost complete conversion and good to excellent enantiomeric purity of the products.

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“…RmL was chosen as biocatalyst for the present investigation. This enzyme has been frequently applied to biotransformations in scCO 2 (Aaltonen, 1999;Blattner et al, 2006), for example, for the esterification of myristic acid with ethanol (Bernard and Barth, 1995), ibuprofen with propanol (Rantakylae and Aaltonen, 1994), as well as in transesterification reactions (Chulalaksananukul et al, 1993;Liu et al, 2006). In order to prepare the RmL-loaded APCNs, 30 mm thick films of PHEA-l-PDMS as well as PHEA-l-PFPE conetworks in varying compositions were immersed into a RmL solution (16.6 mg/mL) and incubated at 48C for 14 h, followed by spectrophotometric determination of the enzyme loading.…”

Section: Loading Of Apcns With Lipase From Rhizomucor Mieheimentioning

confidence: 99%

Amphiphilic conetworks as activating carriers for the enhancement of enzymatic activity in supercritical CO₂

Bruns

Bannwarth

Tiller

2008

Biotech & Bioengineering

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Enzymatic reactions in supercritical carbon dioxide (scCO2) represent a way of combining the advantages of biocatalysis with the environmental benign nature of scCO2 as a solvent. Here we demonstrate that activities of enzymes in scCO2 can be greatly enhanced by incorporating them into amphiphilic conetworks (APCNs), a novel type of enzyme support. Two sets of hydrophilic/scCO2-philic APCNs, poly(2-hydroxyethyl acrylate)-linked by-poly(dimethylsiloxane) (PHEA-l-PDMS) and poly(2-hydroxyethyl acrylate)-linked by-perfluoropolyether (PHEA-l-PFPE), were prepared and loaded with the synthetically relevant lipase from Rhizomucor miehei. The effect of the APCNs' composition on the amount of the absorbed lipase was studied. It is observed that both sets of lipase-loaded APCNs enhance the catalytic activity of the enzyme in scCO2. The chemical nature of the scCO2-philic phase as well as the conetworkscomposition greatly influences the activity of the lipase in the conetworks. Activities obtained with PFPE-basedAPCNS were up to 10-fold higher than those obtained with PDMS-based conetworks. The highest specific activity measured corresponds to a 2,000-fold activation compared to the lyophilized enzyme powder. This activity is 10 times higher than the specific activity of the lipase immobilized on an optimized commercial carrier.

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Enantioselective esterification of ibuprofen in supercritical carbon dioxide by immobilized lipase

Cited by 48 publications

References 10 publications

Biocatalysis using lipase encapsulated in microemulsion-based organogels in supercritical carbon dioxide

Biocatalysis using lipase encapsulated in microemulsion-based organogels in supercritical carbon dioxide

Lipase-Catalyzed Kinetic Resolution of 1-(2-Hydroxycyclohexyl)Indoles in Batch and Continuous-Flow Systems

Amphiphilic conetworks as activating carriers for the enhancement of enzymatic activity in supercritical CO₂

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Enantioselective esterification of ibuprofen in supercritical carbon dioxide by immobilized lipase

Cited by 48 publications

References 10 publications

Biocatalysis using lipase encapsulated in microemulsion-based organogels in supercritical carbon dioxide

Biocatalysis using lipase encapsulated in microemulsion-based organogels in supercritical carbon dioxide

Lipase-Catalyzed Kinetic Resolution of 1-(2-Hydroxycyclohexyl)Indoles in Batch and Continuous-Flow Systems

Amphiphilic conetworks as activating carriers for the enhancement of enzymatic activity in supercritical CO2

Contact Info

Product

Resources

About

Amphiphilic conetworks as activating carriers for the enhancement of enzymatic activity in supercritical CO₂