Optimization of organic solvent in multiphase biocatalysis

Brink, L.E.S.; Tramper, J.

doi:10.1002/bit.260270822

Cited by 254 publications

(64 citation statements)

References 17 publications

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“…Several parameters have been used to correlate solvent toxicity and cellular biocatalytic activity in two-phase reaction media. Apolar solvents having a low Hildebrandt solubility parameter (6) and high molecular weight show high biocatalytic activity retention for epoxidizing cells (Brink and Tramper, 1985). Better correlation between biocatalytic activity and hydrophobicity is found when hydrophobicity is expressed by its lgPoCmol (Laane, 1987, Laane et al, 1987b.…”

Section: Toxic Eflects In Two-phase Reaction Mediamentioning

confidence: 99%

“…The solubility parameter can also be used as a parameter to express the polarity of organic solvents. Brink and Tramper (1985) have found a correlation between the polarity of an organic solvent (expressed by 6) in combination with a high molecular weight of the organic solvent and biocatalytic activity. Vermue et al (1992) have attempted to correlate the lipase-catalysed transesterification rate in supercritical C02 and the Hildebrandt solubility parameter of the medium in a similar way, but the biocatalytic activity seems to be hardly influenced by this parameter.…”

Section: Activitymentioning

confidence: 99%

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Biocatalysis in non-conventional media: Medium engineering aspects (Technical Report)

Vermuë¹,

Tramper²

1995

Pure and Applied Chemistry

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Section: Toxic Eflects In Two-phase Reaction Mediamentioning

confidence: 99%

Section: Activitymentioning

confidence: 99%

Biocatalysis in non-conventional media: Medium engineering aspects (Technical Report)

Vermuë¹,

Tramper²

1995

Pure and Applied Chemistry

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“…;etate; 0, n-pentyl acetate; ., n-hexyl acetate; methyl acetate [the dotted line is drawn supposing that the saturating concentration is the same as that of ethyl acetate, 6.6% (vjv)]. 4). This obviously differs from the results in other kinds of organic solvents: this result is different from that observed by Pliura et al 22) The results from Figs.…”

Section: Rio Io() 110mentioning

confidence: 99%

Modification Effects of Organic Solvents on Microenvironment of the Enzyme in Thermolysin-catalyzed Peptide Synthesis ofN-(Benzyloxycarbonyl)-l-phenylalanyl-l-phenylalanine Methyl Ester

Inagaki

Tadasa

Kayahara

1994

Bioscience, Biotechnology, and Biochemistry

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“…Immobilization of the cells in hydrophilic gels (calcium alginate, K-carrageenan), however, prevents direct cell-organic solvent contact and provides protection against denaturing solvent effects. High activity retention is favoured by low polar/high molecular weight solvents (Brink & Tramper, 1985). The polarity of the support material can also be decisive for the partitioning of substrates and products among the various phases (Brink etal., 1988).…”

Section: Applications Of Epoxidation Reactions In Biotechnological Prmentioning

confidence: 99%

Biocatalysts for production of chiral epoxides

Mahmoudian

Michael

1992

Appl Microbiol Biotechnol

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An extensive screen for microorganisms capable of growth on olefins was carried out. Over 100 bacterial strains (mesophilic, thermophilic) were isolated in pure culture with gaseous or liquid (internal & terminal) olefins as the sole source of carbon and energy. The organisms included Aero coccus, Aeromonas,Alcaligenes, Flavobacterium, Micrococcus, Moraxella, Nocardia, Pseudomonas, Staphylococcus, Streptomyces and Vibrio spp. and a variety of Gram-negative, Gram-positive and Gram-variable rods/coccobacilli not yet identified. Given the success of isolating many different genera of alkene-utilizing bacteria, it would suggest that the ability to utilize olefin hydrocarbons is more widespread in nature than previously recognized.Initial studies involved testing a collection of strains for i) growth rate on the substrate of isolation and ii) evidence of epoxide accumulation from lower gaseous olefins. All of the 18 ethene-and propene-utilizing bacteria tested, stereospecifically formed R-1,2-epoxypropane (ee=90-96%), R -l,2-epoxybutane (ee=90-98%) and trans-(2/?,37?)-epoxybutane (ee=64-88%), as analyzed by chiral complexation glc. A particularly promising strain of Micrococcus sp. M90C was selected to demonstrate: a) Induction of epoxidation activity in carbohydrate-grown cells. b) Optimization of a biotransformation process for production of epoxyethane. c) Involvement of a specific monooxygenase in the formation of chiral epoxides. d) Stereoselectivity of epoxyalkane degradation. e) Substrate specificity toward a range of olefins.Micrococcus sp. M90C stereospecifically formed S-(+)-phenyl glycidyl ether (ee=93%) and /?-(+)-phenyl methyl sulphoxide (ee>98%), as analyzed by chiral-shift NMR and HPLC. The ability to catalyze heteroatom oxygenation as well as epoxidation of a wide range of olefins in high optical and chemical yields, demonstrates its potential as a 'general-purpose' biocatalyst for the production of optically pure oxygenated compounds.Two other promising ethene-utilizing bacteria (M26, M93 A) each catalyzed the stereospecific formation of S-(+)-phenyl glycidyl ether (ee=93%). This has attracted considerable industrial interest and is currently under investigation at ICI for commercial production of optically active./1-blockers. In addition to Micrococcus sp. M90C, the substrate specificities of 6 other organisms were studied in order to probe the active site of the enzymes involved. The pattern of reactivity for the group of 4 ethene-(M26, M90C, M93A, M186) and 2 propene-(M142, M l 56) utilizers differed from that expected with peracids, suggesting a considerable degree of enzymatic control.The nature of the substrate, however, modulated enzymatic epoxidations in Staphylcoccus sp. M97B. CONTENTS

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Optimization of organic solvent in multiphase biocatalysis

Cited by 254 publications

References 17 publications

Biocatalysis in non-conventional media: Medium engineering aspects (Technical Report)

Biocatalysis in non-conventional media: Medium engineering aspects (Technical Report)

Modification Effects of Organic Solvents on Microenvironment of the Enzyme in Thermolysin-catalyzed Peptide Synthesis ofN-(Benzyloxycarbonyl)-l-phenylalanyl-l-phenylalanine Methyl Ester

Biocatalysts for production of chiral epoxides

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