Microbial reduction of ethyl acetoacetate to ethyl (R)-3-hydroxybutyrate in an ionic liquid containing system

He, Jianguo; Zhou, Limin; Wang, Pu; Zu, Lei

doi:10.1016/j.procbio.2008.11.007

Cited by 46 publications

(21 citation statements)

References 37 publications

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“…Ionic liquids containing chloride anions completely inhibited the growth of E. coli MG1655 [87], which is not surprising, as chloride-containing ionic liquids inactivated hydrolases. P. membranaefaciens tolerated 2.5% BMIM(BF 4 ), and even improved the yield and selectivity of the reduction of ethyl acetoacetate to ethyl-(R)-3-hydroxybutyate as compared to buffer [95]. Immobilized baker's yeast in 10 vol% BMIM(BF 4 ) catalyzed the reduction of acetyltrimethylsilane to (S)-1-trimethylsilylethanol [96].…”

Section: Fçåáå=iáèìáçë=~ë=`çëçäîéåíë=mentioning

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: Fçåáå=iáèìáçë=~ë=`çëçäîéåíë=mentioning

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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“…Effects of residual water content [367][368][369][370], pH value [371], miscibility with water [372], as well as the kind of microorganism must not be neglected.…”

Section: Whole-cell Biocatalysis In Ionic Liquids and Deep Eutectic Smentioning

confidence: 99%

Yeast‐Mediated Stereoselective Synthesis

Csük

2016

Green Biocatalysis

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“…In order to reduce the side effect of toxic enantiomers and to remove those enantiomers with less desired biological activities, research work related to the synthesis of both chiral drugs and chiral drug intermediates with high optical purity has been the focus of pharmaceutical industry [3][4][5]. Additionally, techniques for the synthesis of chiral compounds are also crucial in chemical industries because large quantities of chiral chemicals are in great demand in diverse chemical industries such as agriculture and flavor [2,6,7]. β-Hydroxyesters represented by ethyl 3-hydroxybutyrate (EHB) are one class of crucial intermediates for the synthesis of chiral drugs and chiral chemicals.…”

Section: Introductionmentioning

confidence: 99%

“…β-Hydroxyesters represented by ethyl 3-hydroxybutyrate (EHB) are one class of crucial intermediates for the synthesis of chiral drugs and chiral chemicals. For example, optically pure ethyl (R)-3-hydroxybutyrate (R-EHB) has been utilized as a versatile chiral starting material in the synthesis of β-lactamase inhibitors as well as many chiral fine chemicals [7,8]. Ethyl (S)-3-hydroxybutyrate (S-EHB) is an important chiral intermediate of carbapenem antibiotics and insect pheromones [9,10].…”

Section: Introductionmentioning

confidence: 99%

“…Whole cells harboring dehydrogenases have also been employed to synthesize S-EHB. However, biocatalysis methods using whole cells suffer from following disadvantages: The concentrations of substrates in reactions are quite low due to toxicity to cells, optical purity of desired chiral products are not high enough, and tedious methods need to be established to isolate and purify desired chiral products [7,15].…”

Section: Introductionmentioning

confidence: 99%

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Functional Characterization of a Robust Marine Microbial Esterase and Its Utilization in the Stereo-Selective Preparation of Ethyl (S)-3-Hydroxybutyrate

Wang

Zhang

2016

Appl Biochem Biotechnol

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One novel microbial esterase PHE21 was cloned from the genome of Pseudomonas oryzihabitans HUP022 identified from the deep sea of the Western Pacific. PHE21 was heterologously expressed and functionally characterized to be a robust esterase which behaved high resistance to various metal ions, organic solvents, surfactants, and NaCl. Despite the fact that the two enantiomers of ethyl 3-hydroxybutyrate were hard to be enzymatically resolved before, we successfully resolved racemic ethyl 3-hydroxybutyrate through direct hydrolysis reactions and generated chiral ethyl (S)-3-hydroxybutyrate using esterase PHE21. After process optimization, the enantiomeric excess, the conversion rate, and the yield of desired product ethyl (S)-3-hydroxybutyrate could reach 99, 65, and 87 %, respectively. PHE21 is a novel marine microbial esterase with great potential in asymmetric synthesis as well as in other industries.

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Microbial reduction of ethyl acetoacetate to ethyl (R)-3-hydroxybutyrate in an ionic liquid containing system

Cited by 46 publications

References 37 publications

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

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

Yeast‐Mediated Stereoselective Synthesis

Functional Characterization of a Robust Marine Microbial Esterase and Its Utilization in the Stereo-Selective Preparation of Ethyl (S)-3-Hydroxybutyrate

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