Lipase-catalyzed synthesis of glucose fatty acid ester using ionic liquids mixtures

Lee, Sang Hyun; Ha, Sung Ho; Hiệp, Nguyễn Minh; Chang, Woo-Jin; Koo, Yoon‐Mo

doi:10.1016/j.jbiotec.2007.11.001

Cited by 102 publications

(47 citation statements)

References 14 publications

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“…The rates of esterification and transesterification of glucose were approximately 10-fold faster in these supersaturated solutions. Unfortunately, lipase CALB showed poor stability in in BMIM(CF 3 SO 3 ), so a 1:1 mixture of BMIM(CF 3 SO 3 ) and BMIM[TF 2 N] was a compromise between enzyme stability and glucose solubility [57].…”

Section: Ionic Liquids As Non-aqueous Solventsmentioning

confidence: 99%

Toward advanced ionic liquids. Polar, enzyme-friendly solvents for biocatalysis

Gorke

Srienc

Kazlauskas

2010

Biotechnol Bioproc E

253

159

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Ionic liquids, also called molten salts, are mixtures of cations and anions that melt below 100 o C. Typical ionic liquids are dialkylimidazolium cations with weakly coordinating anions such as (MeOSO 3 ) or (PF 6 ). Advanced ionic liquids such as choline citrate have biodegradable, less expensive, and less toxic anions and cations. Deep eutectic solvents are also included in the advanced ionic liquids. Deep eutectic solvents are mixtures of salts such as choline chloride and uncharged hydrogen bond donors such as urea, oxalic acid, or glycerol. For example, a mixture of choline chloride and urea in 1:2 molar ratio liquefies to form a deep eutectic solvent. Their properties are similar to those of ionic liquids. Water-miscible ionic liquids as cosolvents with water enhance the solubility of substrates or products. Although traditional water-miscible organic solvents also enhance solubility, they often inactivate enzymes, while ionic liquids do not. The enhanced solubility of substrates can increase the rate of reaction and often increases the regioor enantioselectivity. Ionic liquids can also be solvents for non-aqueous reactions. In these cases, they are especially suited to dissolve polar substrates. Polar organic solvent alternatives inactivate enzymes, but ionic liquids do not even when they have similar polarities. Besides their solubility properties, ionic liquids and deep eutectic solvents may be greener than organic solvents because ionic liquids are nonvolatile, and can be made from nontoxic components. This review covers selected examples of enzyme catalyzed reaction in ionic liquids that demonstrate their advantages and unique properties, and point out opportunities for new applications. Most examples involve hydrolases, but oxidoreductases and even whole cell reactions have been reported in ionic liquids. © KSBB hÉóïçêÇëW=áçåáÅ=äáèìáÇëI=ÇÉÉé=ÉìíÉÅíáÅ=ëçäîÉåíëI=ÜóÇêçä~ëÉëI=çñáÇçêÉÇìÅí~ëÉëI=éçäóãÉêáò~íáçå= = = = = IONIC LIQUIDS AND DEEP EUTECTIC SOLVENTSIonic liquids, also called molten salts, are mixtures of cations and anions that melt below 100 o C. The low melting point stems from a mismatch in the size of the anion and cation that prevents crystallization. Changing the structures of the anions or cations can tune the polarities and other properties. Even though they are salts, their polarities are only moderate, similar to ethanol. Ionic liquids have negligible vapor pressure. Ionic liquids are viscous, typically 0.1 Pas or more, which is similar to glycerol or honey.The first ionic liquid -ethylammonium nitrate (mp 12 o C) -was reported in 1914 [1], but attracted limited use. The first generation of widely studied ionic liquids used the dialkylimmidazolium and related cations reported in 1982 [2], Fig. 1. Varying the cation structure varied the properties of the ionic liquid. The anions were chloroaluminate or other metal halide anions, which react with water and thus are not suited for biotransformations. The second generation of ionic liquids, discovered a decade later [3], replaced the water r...

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Section: Ionic Liquids As Non-aqueous Solventsmentioning

confidence: 99%

Toward advanced ionic liquids. Polar, enzyme-friendly solvents for biocatalysis

Gorke

Srienc

Kazlauskas

2010

Biotechnol Bioproc E

253

159

View full text Add to dashboard Cite

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“…As displayed in Table 1 4 ] is prone to desorb water from the enzyme surface and thus decrease the enzyme performance (21). The effect of the alkyl chain length on imidazolium cation based on the [PF 6 ] anion has also been investigated.…”

Section: Resultsmentioning

confidence: 99%

Enantioselective esterification of (R,S)-flurbiprofen catalyzed by lipase in ionic liquid

Zhao

Zhang

Zheng

et al. 2016

Green Chemistry Letters and Reviews

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The enantioselective esterification of (R,S)-flurbiprofen catalyzed by Candida sp. lipase (CSL) (a cheap commercial lipase) was successfully conducted in ionic liquid (IL). The effects of the type of IL, alcohol, temperature, substrate molar ratio and enzyme concentration were investigated. Under optimal conditions (flurbiprofen (0.2 mmol), methanol (2 mmol), CSL (4 mg/mL), [BMIM][PF 6 ] (5 mL), 50°C), CSL exhibited a satisfying enzyme performance (average enzyme activity, 261.5 μmol/g/h; E value, 20.3). The enzymatic esterification can be scaled up easily. Furthermore, CSL exhibited only a slight decrease in catalytic performance after six repetitions. This result demonstrated that this mild method has high potential for industrial production. ARTICLE HISTORY

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“…Our group recently reported that the enzyme activity and stability could be significantly increased by using supersaturated sugar solutions in ILs mixture through water-mediated method in the synthesis of sugar esters [16,17]. However, decreased enzyme activity was obtained although much higher enzyme stability was achieved in [Bmim][TfO] and [Omim][Tf 2 N] mixture (1:1, v/v) selected as the best reaction media in terms of enzyme activity and stability [17].…”

Section: Introductionmentioning

confidence: 99%

“…However, decreased enzyme activity was obtained although much higher enzyme stability was achieved in [Bmim][TfO] and [Omim][Tf 2 N] mixture (1:1, v/v) selected as the best reaction media in terms of enzyme activity and stability [17]. As a result, the enhancement of enzyme activity in ILs mixture is still a challenging problem in the commercialization of a biosynthetic system of sugar esters using ILs mixture as the reaction media.…”

Section: Introductionmentioning

confidence: 99%

Enhanced production of fructose palmitate by lipase-catalyzed esterification in ionic liquids

Hiệp

Koo

2010

Biotechnol Bioproc E

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For the enhancement of enzyme activity, application of ultrasound irradiation on lipase-catalyzed esterification of fructose with palmitic acid in ionic liquids (ILs) mixture containing supersaturated fructose solution was investigated. In the mixture of [Bmim][TfO] and [Omim][Tf 2 N] (1:1, v/v), 1.44 times higher enzyme activity (29.2 µmoL/min/g) was achieved under ultrasound irradiation. Besides, ultrasound irradiation enhanced enzyme stability in viscous ILs mixture. After 5 times reuse of Novozym 435 and ILs mixture, 84.4% of initial enzyme activity was remained under ultrasound irradiation, while the residual activity using magnetic stirring only method was 76.2%. These results show that enzymatic reaction in viscous ILs mixture under ultrasound irradiation is an effective method for enzyme activity, as well as, enzyme stability resulting in economic competitiveness of green process. © KSBB hÉóïçêÇëW=áçåáÅ=äáèìáÇëI=ÑêìÅíçëÉ=é~äãáí~íÉI=ï~íÉê=ÅçåíÉåíI=ìäíê~ëçìåÇ=áêê~Çá~íáçå= = = = =

show abstract

Lipase-catalyzed synthesis of glucose fatty acid ester using ionic liquids mixtures

Cited by 102 publications

References 14 publications

Toward advanced ionic liquids. Polar, enzyme-friendly solvents for biocatalysis

Toward advanced ionic liquids. Polar, enzyme-friendly solvents for biocatalysis

Enantioselective esterification of (R,S)-flurbiprofen catalyzed by lipase in ionic liquid

Enhanced production of fructose palmitate by lipase-catalyzed esterification in ionic liquids

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