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Ionic liquids in whole-cell biocatalysis: a compromise between toxicity and efficiency

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Abstract

Comparison of chemical catalysis by metal complexes, enzymatic catalysis and whole-cell biocatalysis shows well-addressed advantages of the latter approach. However, a critical limitation in the practical applications originates from the high sensitivity of microorganisms to the toxic effects of organic solvents. In the present review, we consider toxic solvent properties of ionic liquid/water systems towards the development of efficient applications in practical organic transformations.

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Abbreviations

AMMOENG™ 100:

Cocosalkylpenthaethoxymethylammonium methylsulfate

[CnMIM]:

1-alkyl-3-methylimidazolium

[HOC2MIM]:

(2-hydroxy)ethyl-3-methylimidazolium

[CnC1MIM]:

1-alkyl-2,3-dimethylimidazolium

[PPMIM]:

1-phenylpropyl-3-methylimidazolium

[AMIM]:

1-allyl-3-methylimidazolium

[BzMIM]:

1-benzyl-3-methylimidazolium

[HOOC2MIM]:

1-carboxymethyl-3-methylimidazolium

[CnPy]:

N-alkylpyridinium

[CnMPy]:

N-alkyl-3-methyl-pyridinium

[CnMPyr]:

N-alkyl-N-methylpyrrolidinium

[CnMPip]:

N-alkyl-N-methylpiperidinium

[(C1OC3)C1Pip]:

N-methyl-N-(1-methoxypropyl)-piperidinium

[CnCnCnCnN]:

N,N,N,N-tetraalkylammonium

[Chol]:

cholinium, N-(2-hydroxy)ethyl- N,N,N-trimethylammonium

[(HOC2)(C1)2N]:

N,N-dimethyl-N-ethanolammonium

[(HOC2)2C4C2N]:

N,N-di(2-hydroxy)ethyl- N-butyl-N-ethylammonium

[(HOC3)C2(C1)2N]:

N-(3-hydroxy)propyl- N-ethyl-N,N-dimethylammonium

[(HOC3)C4(C1)2N]:

N-(3-hydroxy)propyl- N-butyl-N,N-dimethylammonium

[(HOC2)3C1N]:

Tris(2-hydroxyethyl)methylammonium

[CnCnCnCnN]:

Tetraalkylphosphonium

[(HOC3)3C10P]:

Decyltris(3-hydroxypropyl)phosphonium

[(C1)4C2Gua]:

N,N,N’,N’-tetramethyl-N”-ethylguanidinium

[CABHEM]:

PEG-5 cocomonium

[BF4]:

Tetrafluoroborate

[PF6]:

Hexafluorophosphate

[OTf]:

Trifluoromethanesulfonate

[NTf2]:

Bis(trifluoromethylsulfonyl)imide

[(C2F5)3PF3]:

Tris(pentafluoroethyl)trifluorophosphate

[N(CN)2]:

Dicyanamide

[SCN]:

Thiocyanate

[NO3]:

Nitrate

[OAc]:

Acetate

[C2COO]:

Propanoate

[C5COO]:

Hexanoate

[C1PO3]:

Methylphosphonate

[C2PO4]:

Dimethylphosphate

[i-(C8)2PO4]:

Bis(2,4,4-trimethylpentyl)phosphinate

[C2SO3]:

Ethylsulfonate

[CnSO4]:

Alkylsulfate

[CnOCnSO4]:

2-alkoxyalkylsulfate

[C1(OC2)3SO4]:

2-[2-(2-methoxy)ethoxy]ethoxyethylsulfate

[Tos]:

Tosylate, p-toluenesulfonate

[MDEGSO4]:

Ethylenglycolmonomethylethersulfate

[SbF6]:

Hexafluoroantimonate

[Lac]:

Lactate

[Sacch]:

Saccharinate

[Doc]:

Docusate

[Lin]:

Linoleate

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Acknowledgements

This work was supported by the Russian Foundation for Basic Research (grant 16-29-10804).

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Authors and Affiliations

  1. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospekt 47, Moscow, 119991, Russia

    Ksenia S. Egorova & Valentine P. Ananikov

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  1. Ksenia S. Egorova
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  2. Valentine P. Ananikov
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Correspondence to Valentine P. Ananikov.

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Ksenia S. Egorova declares that she has no conflict of interest. Valentine P. Ananikov declares that he has no conflict of interest.

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This article does not contain any studies with human participants or animals performed by any of the authors.

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This article is part of a Special Issue on ‘Ionic Liquids and Biomolecules’ edited by Antonio Benedetto and Hans-Joachim Galla.

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Egorova, K.S., Ananikov, V.P. Ionic liquids in whole-cell biocatalysis: a compromise between toxicity and efficiency. Biophys Rev 10, 881–900 (2018). https://doi.org/10.1007/s12551-017-0389-9

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