Supported liquid membrane as a novel tool for driving the equilibrium of ω-transaminase catalyzed asymmetric synthesis

Rehn, Gustav; Adlercreutz, Patrick; Grey, Carl

doi:10.1016/j.jbiotec.2014.03.022

Cited by 50 publications

(56 citation statements)

References 30 publications

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“…ALA represents the key to high purities since it is not extracted compared to using IPA as an amine donor. 31 In the following we give a brief description of the general applicability of the s-ISPR to a broad range of amine products and its extraction principle depicted in Scheme 1. In principle, any amine which is soluble in organic solvents could be extracted, purified, and enriched.…”

Section: Resultsmentioning

confidence: 99%

“…29 The principle of selective removal/recovery of the amine product renders thereby perhaps an even more promising strategy in asymmetric amine synthesis. 30 Rehn et al presented the production of α-methylbenzylamine from acetophenone together with IPA as an amine donor using supported-liquid membrane (SLM) extraction as ISPR method, 31 which affords high product concentrations (about 100 g/L). 32 The principle of SLM extraction is schematically illustrated in Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

“…13 If IPA serves as amine donor, partial coextraction is unavoidable (Scheme 1, blue frames). 31 However, if the amine donor features a permanently charged character at high pH such as the zwitter-ionic ALA (Scheme 1, red frames), coextraction would be avoided, and ALA is thus an ideal candidate in this respect. Furthermore, as depicted in Scheme 1, the coproduct (PYR) will not cross the membrane either, and hence the ALA reaction should facilitate a much higher amine product purity compared to IPA.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

A Process Concept for High-Purity Production of Amines by Transaminase-Catalyzed Asymmetric Synthesis: Combining Enzyme Cascade and Membrane-Assisted ISPR

Börner

Rehn

Grey

et al. 2015

Org. Process Res. Dev.

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For the amine transaminase (ATA)-catalyzed synthesis of chiral amines, the choice of donor substrate is of high importance for reaction and process design. Alanine was investigated as an amine donor for the reductive amination of a poorly water-soluble ketone (4-phenyl-2-butanone) in a combined in situ product removal (ISPR) approach using liquid-membrane extraction together with an enzyme cascade. This ISPR strategy facilitates very high (>98%) product purity with an integrated enrichment step and eliminates product as well as coproduct inhibition. In the presented proof-of-concept alanine shows the following advantages over the other frequently employed amine donor isopropyl amine: (i) nonextractability of alanine affords high product purity without any additional downstream step and no losses via coextraction, (ii) higher maximum reaction rates, and (iii) broader acceptance among ATAs.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

A Process Concept for High-Purity Production of Amines by Transaminase-Catalyzed Asymmetric Synthesis: Combining Enzyme Cascade and Membrane-Assisted ISPR

Börner

Rehn

Grey

et al. 2015

Org. Process Res. Dev.

Self Cite

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“…The system enabled continuous extraction of the amine product and was used to successfully shift the equilibrium in asymmetric synthesis of (S)-α-methylbenzylamine (5). A conversion of 98% was reached, compared to 50% without product extraction [118]. This system was further improved by implementing continuous control of the reactor pH using the amine donor substrate, and regeneration of the supported liquid membrane unit at regular intervals to maintain the extraction performance [119].…”

Section: Liquid Membranesmentioning

confidence: 99%

Chiral Separation in Preparative Scale: A Brief Overview of Membranes as Tools for Enantiomeric Separation

2017

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Given the importance of chirality in the biological response, regulators, industries and researchers require chiral compounds in their enantiomeric pure form. Therefore, the approach to separate enantiomers in preparative scale needs to be fast, easy to operate, low cost and allow obtaining the enantiomers at high level of optical purity. A variety of methodologies to separate enantiomers in preparative scale is described, but most of them are expensive or with restricted applicability. However, the use of membranes have been pointed out as a promising methodology for scale-up enantiomeric separation due to the low energy consumption, continuous operability, variety of materials and supports, simplicity, eco-friendly and the possibility to be integrated into other separation processes. Different types of membranes (solid and liquid) have been developed and may provide applicability in multi-milligram and industrial scales. In this brief overview, the different types and chemical nature of membranes are described, showing their advantages and drawbacks. Recent applications of enantiomeric separations of pharmaceuticals, amines and amino acids were reported.

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“…A supported liquid membrane (SLM) system combined with a packed bed reactor enables continuous extraction of the amine product [43]. A conversion of 98% was reached with the extraction step using SLM, compared to 50% without the extraction step with SLM.…”

Section: Equilibrium Shift Via Supported Liquid Membranementioning

confidence: 99%

Transaminases and their Applications

2016

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Supported liquid membrane as a novel tool for driving the equilibrium of ω-transaminase catalyzed asymmetric synthesis

Cited by 50 publications

References 30 publications

A Process Concept for High-Purity Production of Amines by Transaminase-Catalyzed Asymmetric Synthesis: Combining Enzyme Cascade and Membrane-Assisted ISPR

A Process Concept for High-Purity Production of Amines by Transaminase-Catalyzed Asymmetric Synthesis: Combining Enzyme Cascade and Membrane-Assisted ISPR

Chiral Separation in Preparative Scale: A Brief Overview of Membranes as Tools for Enantiomeric Separation

Transaminases and their Applications

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