Impacts of ionic liquids on enzymatic synthesis of glucose laurate and optimization with superior productivity by response surface methodology

Lin, Xiao‐Sheng; Wen, Qing; Huang, Zelin; Cai, Yu-Zheng; Halling, Peter J.; Yang, Zhen

doi:10.1016/j.procbio.2015.07.019

Cited by 29 publications

(31 citation statements)

References 32 publications

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“…The increase in productivity is likely caused by the difference in solvent polarity as solvent polarity is already reported to have an effect on glycolipid synthesis in organic solvents [26,27]. In ionic liquids, it is also reported that medium polarity is most appropriate to dissolve sugar as well as fatty acids [28]. The solvatochromic π* is a measure of polarizability and dipolarity of solvents.…”

Section: Discussionmentioning

confidence: 99%

“…Enzyme stability is reduced in polar solvents due to stripping off hydration water from the enzyme [25]. Solvents of medium polarity present a compromise between enzyme stability and sugar solubility and showed, therefore, highest yields in organic solvents as well as in ionic liquids [26][27][28]. Furthermore, fatty acid availability is a limiting factor of glycolipid synthesis in hydrophilic DES [24].…”

Section: Introductionmentioning

confidence: 99%

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Enzymatic Synthesis of Glucose Monodecanoate in a Hydrophobic Deep Eutectic Solvent

Hollenbach

Ochsenreither

Syldatk

2020

IJMS

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Environmentally friendly and biodegradable reaction media are an important part of a sustainable glycolipid production in the transition to green chemistry. Deep eutectic solvents (DESs) are an ecofriendly alternative to organic solvents. So far, only hydrophilic DESs were considered for enzymatic glycolipid synthesis. In this study, a hydrophobic DES consisting of (-)-menthol and decanoic acid is presented for the first time as an alternative to hydrophilic DES. The yields in the newly introduced hydrophobic DES are significantly higher than in hydrophilic DESs. Different reaction parameters were investigated to optimize the synthesis further. Twenty milligrams per milliliter iCalB and 0.5 M glucose resulted in the highest initial reaction velocity for the esterification reaction, while the highest initial reaction velocity was achieved with 1.5 M glucose in the transesterification reaction. The enzyme was proven to be reusable for at least five cycles without significant loss of activity.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Enzymatic Synthesis of Glucose Monodecanoate in a Hydrophobic Deep Eutectic Solvent

Hollenbach

Ochsenreither

Syldatk

2020

IJMS

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“…In contrast, direct quantification enables the identification and monitoring of different reaction phases, i.e., the transition from formation of monoesters to di-or polyesters. In the studies where a direct glycolipid quantification via HPLC was performed, refractive index detection was used (Castillo et al, 2003;Lin et al, 2015;Zhao et al, 2016). However, refractive index detection is incompatible with gradient elution, but ELSD detection allows for this (Clement et al, 1992;Swartz, 2010).…”

Section: Discussionmentioning

confidence: 99%

“…In organic solvents, the reaction yield in glycolipid synthesis with butanone as solvent is higher than with the more polar solvents acetone and t-butanol (Šabeder et al, 2006;Bouzaouit and Bidjou-haiour, 2016). Various IL investigations have shown that a compromise between highly hydrophilic ILs for good sugar solubility and highly hydrophobic IL for good fatty acid solubility is needed to achieve good conversion rates (Lin et al, 2015). Thus, both literature and the reported experimental results show that the polarity of the solvent is another factor that plays a role in glycolipid synthesis in DES.…”

Section: Discussionmentioning

confidence: 99%

Optimization of Glycolipid Synthesis in Hydrophilic Deep Eutectic Solvents

Hollenbach

Bindereif

Schaaf

et al. 2020

Front. Bioeng. Biotechnol.

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Glycolipids are considered an alternative to petrochemically based surfactants because they are non-toxic, biodegradable, and less harmful to the environment while having comparable surface-active properties. They can be produced chemically or enzymatically in organic solvents or in deep eutectic solvents (DES) from renewable resources. DES are non-flammable, non-volatile, biodegradable, and almost non-toxic. Unlike organic solvents, sugars are easily soluble in hydrophilic DES. However, DES are highly viscous systems and restricted mass transfer is likely to be a major limiting factor for their application. Limiting factors for glycolipid synthesis in DES are not generally well understood. Therefore, the influence of external mass transfer, fatty acid concentration, and distribution on initial reaction velocity in two hydrophilic DES (choline:urea and choline:glucose) was investigated. At agitation speeds of and higher than 60 rpm, the viscosity of both DES did not limit external mass transfer. Fatty acid concentration of 0.5 M resulted in highest initial reaction velocity while higher concentrations had negative effects. Fatty acid accessibility was identified as a limiting factor for glycolipid synthesis in hydrophilic DES. Mean droplet sizes of fatty acid-DES emulsions can be significantly decreased by ultrasonic pretreatment resulting in significantly increased initial reaction velocity and yield (from 0.15 ± 0.03 µmol glucose monodecanoate/g DES to 0.57 ± 0.03 µmol/g) in the choline: urea DES. The study clearly indicates that fatty acid accessibility is a limiting factor in enzymatic glycolipid synthesis in DES. Furthermore, it was shown that physical pretreatment of fatty acid-DES emulsions is mandatory to improve the availability of fatty acids.

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“…enzyme catalyst has been compared and discussed. Our recent study in enzymatic synthesis of glucose laurate has revealed that when lipase (EC 3.1.1.3) was added as the catalyst, among the 16 IL screened tetrabutylammonium acetate ([Bu 4 N][Ac]) was the one in which the highest conversion was obtained [18]. A serendipitous experiment later has revealed that glucose laurate could also be produced in this particular IL in the absence of the enzyme.…”

Section: Introductionmentioning

confidence: 99%

Tetraalkylammonium Ionic Liquids as Dual Solvents–Catalysts for Direct Synthesis of Sugar Fatty Acid Esters

Lin

Zou²,

Zhao

et al. 2016

J Surfact & Detergents

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As nonionic surfactants derived from naturally renewable resources such as sugars and fatty acids, sugar fatty acid esters have been widely utilized in food, cosmetic and pharmaceutical industries. Our present study has demonstrated that the inexpensive and halogen-free tetraalkylammonium salts (e.g., [Bu 4 N][Ac], [Et 4 N][Ac] and [Me 4 N][Ac]) can act as dual solvents-catalysts for regioselective acylation to produce glucose laurate. This non-enzymatic synthesis can proceed under mild conditions with high specificity, and the conversions obtained were superior to that when an enzyme catalyst (lipase, EC 3.1.1.3) was added. A higher yield was obtained in the ammonium salt with a longer alkyl chain on the cation, while no product was obtained in [Bu 4 N][HSO 4 ] and [Bu 4 P][Ac]. A reaction mechanism has been proposed, which is supported by phase-transfer catalysis and law of matching water affinity.

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Impacts of ionic liquids on enzymatic synthesis of glucose laurate and optimization with superior productivity by response surface methodology

Cited by 29 publications

References 32 publications

Enzymatic Synthesis of Glucose Monodecanoate in a Hydrophobic Deep Eutectic Solvent

Enzymatic Synthesis of Glucose Monodecanoate in a Hydrophobic Deep Eutectic Solvent

Optimization of Glycolipid Synthesis in Hydrophilic Deep Eutectic Solvents

Tetraalkylammonium Ionic Liquids as Dual Solvents–Catalysts for Direct Synthesis of Sugar Fatty Acid Esters

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