Novel biocompatible cholinium-based ionic liquids—toxicity and biodegradability

Petković, Marija; Ferguson, Jamie; Gunaratne, H. Q. Nimal; Ferreira, Rui A. C.; Leitão, Maria C.; Seddon, Kenneth R.; Rebelo, Luís Paulo N.; Pereira, Cristina Silva

doi:10.1039/b922247b

Cited by 505 publications

(459 citation statements)

References 24 publications

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“…However, these processes are limited by high costs of conventional ILs, water usage, and toxicity. Recently, attention has shifted to ILs derived from benign cholinium cations stabilized with readily available biobased anions (Petkovic et al, 2010;Sun et al, 2016). A recently demonstrated one-pot process involving biomass pretreatment with ILs composed of cholinium and amino acids followed by enzymatic saccharification requires minimal water and unit operations, thus dramatically lowering process costs (F. Xu et al, 2016).…”

Section: Fatty Alcohol Production From Biomass Sugars Released Using mentioning

confidence: 99%

Engineering high-level production of fatty alcohols by Saccharomyces cerevisiae from lignocellulosic feedstocks

d’Espaux

Ghosh

Runguphan

et al. 2017

Metabolic Engineering

104

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A B S T R A C TFatty alcohols in the C12-C18 range are used in personal care products, lubricants, and potentially biofuels. These compounds can be produced from the fatty acid pathway by a fatty acid reductase (FAR), yet yields from the preferred industrial host Saccharomyces cerevisiae remain under 2% of the theoretical maximum from glucose. Here we improved titer and yield of fatty alcohols using an approach involving quantitative analysis of protein levels and metabolic flux, engineering enzyme level and localization, pull-push-block engineering of carbon flux, and cofactor balancing. We compared four heterologous FARs, finding highest activity and endoplasmic reticulum localization from a Mus musculus FAR. After screening an additional twenty-one single-gene edits, we identified increasing FAR expression; deleting competing reactions encoded by DGA1, HFD1, and ADH6; overexpressing a mutant acetyl-CoA carboxylase; limiting NADPH and carbon usage by the glutamate dehydrogenase encoded by GDH1; and overexpressing the Δ9-desaturase encoded by OLE1 as successful strategies to improve titer. Our final strain produced 1.2 g/L fatty alcohols in shake flasks, and 6.0 g/L in fed-batch fermentation, corresponding to~20% of the maximum theoretical yield from glucose, the highest titers and yields reported to date in S. cerevisiae. We further demonstrate high-level production from lignocellulosic feedstocks derived from ionic-liquid treated switchgrass and sorghum, reaching 0.7 g/L in shake flasks. Altogether, our work represents progress towards efficient and renewable microbial production of fatty acidderived products.

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Section: Fatty Alcohol Production From Biomass Sugars Released Using mentioning

confidence: 99%

Engineering high-level production of fatty alcohols by Saccharomyces cerevisiae from lignocellulosic feedstocks

d’Espaux

Ghosh

Runguphan

et al. 2017

Metabolic Engineering

104

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“…Microorganisms displaying IL tolerance have been screened using direct plating, growth in liquid culture and phenotypic microarrays (Deive et al 2011;Khudyakov et al 2012;Liu et al 2015;Nakashima et al 2011;Petkovic et al 2009;Petkovic et al 2010;Santos et al 2014;Simmons et al 2014;Singer et al 2011;Sitepu et al 2014).…”

Section: Discovering and Screening For Il Tolerant Microorganisms Relmentioning

confidence: 99%

Ionic liquid-tolerant microorganisms and microbial communities for lignocellulose conversion to bioproducts

Simmons

Singer

et al. 2016

Appl Microbiol Biotechnol

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Chemical and physical pretreatment of biomass is a critical step in the conversion of lignocellulose to biofuels and bioproducts. Ionic liquid (IL) pretreatment has attracted significant attention due to the unique ability of certain ILs to solubilize some or all components of the plant cell wall. However, these ILs not only inhibit enzyme activities, but also the growth and productivity of microorganisms used in downstream hydrolysis and fermentation processes.While pretreated biomass can be washed to remove residual IL and reduce inhibition, extensive washing is costly and not feasible in large-scale processes. IL tolerant microorganisms and microbial communities have been discovered from environmental samples and studies begun to elucidate mechanisms of IL tolerance. The discovery of IL tolerance in environmental microbial communities and individual microbes has lead to the proposal of molecular mechanisms of resistance. In this article, we review recent progress on discovering IL tolerant microorganisms, identifying metabolic pathways and mechanisms of tolerance, and engineering microorganisms for IL tolerance. Research in these areas will yield new approaches to overcome inhibition in lignocellulosic biomass bioconversion processes and increase opportunities for the use of ILs in biomass pretreatment.

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“…12 In general, cholinium-based compounds are cheaper than traditional ILs, may be completely derived from renewable sources, and may present outstanding biodegradability and low toxicity. 13 In this context, the use of cholinium-based compounds (salts or ILs) has been proposed as an alternative to increase the sustainable and biocompatible features of IL-based ABS. 14,15,16 Herein, considering the importance of the fulfillment of several green chemistry principles, we propose the use of ABS composed of polyethylene glycol (PEG) polymers (inert and biocompatible) in combination with [Ch] + -salts or ILs.…”

Section: Introductionmentioning

confidence: 99%

Alkaloids as Alternative Probes To Characterize the Relative Hydrophobicity of Aqueous Biphasic Systems

Pereira

Magri

Quental

et al. 2016

ACS Sustainable Chem. Eng.

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In order to overcome the lack of characterization on the relative hydrophobicity of aqueous biphasic systems (ABS), the partition of three alkaloids as alternative probes, was evaluated in a series of biocompatible ABS composed of cholinium-based salts or ionic liquids (ILs) and polyethylene glycol (PEG). The caffeine partitioning in ABS was firstly addressed to infer on the effect of the phase-forming components composition. In all systems, caffeine preferentially concentrates in the lower water content PEG-rich phase. Additionally, a linear dependence between the logarithmic function of the partition coefficients and the water content ratio was found. To confirm this linear dependency, the partition coefficients of caffeine, theobromine and theophylline were determined in other ABS formed by different cholinium-based salts/ILs. In most systems, it is shown that all alkaloids partition to the most hydrophobic phase. To support the experimental results, COSMO-RS (Conductor-like Screening Model for Real Solvents) was used to compute the screening charge distributions of both phaseforming components of ABS and alkaloids, the excess enthalpy of mixing and the activity coefficients at infinite dilution. It is here demonstrated that the partition trend of alkaloids can be used to address the relative hydrophobicity of the coexisting phases in polymer-salt/-IL ABS.

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Novel biocompatible cholinium-based ionic liquids—toxicity and biodegradability

Cited by 505 publications

References 24 publications

Engineering high-level production of fatty alcohols by Saccharomyces cerevisiae from lignocellulosic feedstocks

Engineering high-level production of fatty alcohols by Saccharomyces cerevisiae from lignocellulosic feedstocks

Ionic liquid-tolerant microorganisms and microbial communities for lignocellulose conversion to bioproducts

Alkaloids as Alternative Probes To Characterize the Relative Hydrophobicity of Aqueous Biphasic Systems

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