Biphasic mixture of water, dimethyl sulfoxide, and tetrahydrofuran for use in centrifugal partition chromatography

Foucault, Alain; Durand, Patrick; Frías, Evangelina Camacho; Goffic, F. Le

doi:10.1021/ac00063a038

Cited by 10 publications

(3 citation statements)

References 3 publications

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“…We observed that 25 vol% content of DMSO eventually leads to the destabilization of slug flow in the reaction capillary because such great addition of DMSO cosolvent significantly decreases the interfacial tension (Foucault et al, 1993;Li et al, 1996). Irregular slug flow is coupled with the decrease of interfacial area.…”

Section: Parametrical Studiesmentioning

confidence: 83%

Aldolase catalyzed L-phenylserine synthesis in a slug-flow microfluidic system – Performance and diastereoselectivity studies

Čech

Hessel

Přibyl

2017

Chemical Engineering Science

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L-phenylserine was produced by threonine aldolase in slug-flow microfluidic system. Substrate benzaldehyde was continuously supplied from the organic phase. TBME solvent provides mild conditions and high product concentration. MeTHF solvent provides high concentration of L-syn-phenylserine. Toluene provides low value of syn-anti forms ratio in short residence time. a b s t r a c tWe study synthesis of L-phenylserine catalyzed by the enzyme L-threonine aldolase in a slug-flow microfluidic system. Slug-flow arrangement allows for the continuous refilling of sparingly soluble substrate (benzaldehyde) into an aqueous reaction mixture. We identified suitable composition of an organic phase to provide stable slug-flow in a wide range of operational parameters. Solvent screening revealed that tert-butyl methyl ether (TBME) as the organic solvent provides the most friendly environment for L-phenylserine synthesis due to a low degree of enzyme deactivation and high benzaldehyde concentration in the reaction mixture. The effects of substrate concentrations, enzyme concentration, and dimethylsulfoxide (DMSO) concentration on the L-phenylserine concentration in the product stream were examined and proper reaction conditions were identified. Experimental results on the L-phenylserine diastereoselectivity demonstrate that the amount of syn-conformation of L-phenylserine increases with the reaction time. High syn-to anti-concentration ratio is achieved with 2-methyltetrahydrofuran (MeTHF) solvent in a system with long residence time and, finally, low syn-to anticoncentration ratio is provided by toluene environment and short residence time. (J. Čech), v.hessel@tue.nl (V. Hessel), pribylm@vscht.cz (M. Přibyl). Please cite this article as: Čech, J., et al., Aldolase catalyzed L-phenylserine synthesis in a slug-flow microfluidic system -Performance and diastereoselectivity studies. Chem. Eng. Sci. (2016), http://dx.

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Section: Parametrical Studiesmentioning

confidence: 83%

Aldolase catalyzed L-phenylserine synthesis in a slug-flow microfluidic system – Performance and diastereoselectivity studies

Čech

Hessel

Přibyl

2017

Chemical Engineering Science

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“…The stationary phase is segmented as in DCCC and the process has been described as Centrifugal Droplet CCC (4) although droplet formation need not arise in the mixing process (30,31). Some authors use the abbreviation CPC to refer specifically to CCC carried out in a chambered rotor (hydrostatic apparatus) (7,34), and use the term CCC only for chromatography done in apparatus involving hydrodynamic mixing such as the MLCPC. Others use CPC generically in reference to Centrifugal Partition Chromatography in any type of centrifugal apparatus.…”

Section: History and Modern Apparatusmentioning

confidence: 99%

Overview of Countercurrent Chromatography

Conway

1995

ACS Symposium Series

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Retention and separation in countercurrent chromatography (CCC) is based purely on the liquid-liquid partition coefficients of the solutes since no adsorptive matrix is employed to retain the stationary phase. The liquid stationary phase is held in an inert, coiled tubular column by an inertial force field while the immiscible mobile phase passes through. Droplet CCC as well as more modern coil planet centrifuge and chambered plate chromatographs are described. The theoretical basis of retention and resolution is briefly presented along with a discussion of solvent systems and some applications of this relatively new chromatographic technique.This chapter is intended to introduce the novice to the nature and scope of countercurrent chromatography (CCC) and to present a brief outline of chromatographic theory relating CCC to other forms of chromatography. A comprehensive review of CCC literature is not intended and only selected references will be given. Several monographs and reviews have been published (1-7). The reader is also directed to several special issues of J. Liq. Chromatog. 1984 [no. 2]

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“…Interestingly, the combination of water, DMSO and THF was also proposed by Foucalt et al[8] for the purification of macrolide antibiotics. The ratio of water, DMSO and THF had to be determined.…”

mentioning

confidence: 93%

Separation and purification of xylose oligomers using centrifugal partition chromatography

Lau

Bunnell

Clausen

et al. 2010

J Ind Microbiol Biotechnol

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Xylose oligomers, which have a prebiotic effect, have been used as additives to human and animal food. These oligomers are also the primary intermediate in hemicellulose degradation during the pretreatment of biomass. Centrifugal partition chromatography (CPC) was used in this study to separate and purify xylan-derived oligomers from birchwood xylan. The xylan was partially hydrolyzed to achieve varying degrees of polymerization at 130°C using 0.98% aqueous sulfuric acid for 20 min with a 2.5% solid loading. The CPC solvent system consisting of dimethyl sulfoxide (DMSO), tetrahydrofuran (THF), and water in a 1:6:3 volumetric ratio was used because of its ability to dissolve xylose oligomers of different degrees of polymerization. The CPC was operated in the ascending mode with the water- and DMSO-rich bottom phase acting as the stationary phase, while the THF-rich top phase was the eluent. This paper delineates a method for the production and purification of xylose monomer and xylose oligomers (up to xylopentaose) using CPC. The amount and purity of compounds collected from the CPC fractionation based on 1 g of birchwood xylan were 25.26 mg of xylose at 91.86% purity, 10.71 mg of xylobiose at 85.07% purity, 4.15 mg of xylotriose at 54.71% purity, 5.03 mg of xylotetraose at 38.33% purity and 3.31 mg of xylopentaose at 30.43% purity.

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Biphasic mixture of water, dimethyl sulfoxide, and tetrahydrofuran for use in centrifugal partition chromatography

Cited by 10 publications

References 3 publications

Aldolase catalyzed L-phenylserine synthesis in a slug-flow microfluidic system – Performance and diastereoselectivity studies

Aldolase catalyzed L-phenylserine synthesis in a slug-flow microfluidic system – Performance and diastereoselectivity studies

Overview of Countercurrent Chromatography

Separation and purification of xylose oligomers using centrifugal partition chromatography

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