Resolution of racemic 1-arylethyl acetates by Pseudomonas fluorescens in the presence of a surfactant

Bora, Utpal; Saikia, Chandan J.; Chetia, Apurba; Mishra, Amiyakanta; Kumar, B. Santhosh; Boruah, Romesh C.

doi:10.1016/j.tetlet.2003.10.045

Cited by 7 publications

(4 citation statements)

References 40 publications

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“…1−3 Several landmark methodologies for bringing out the potential of lipase have been developed: lipid coating mediated activation by Okahata, 258,259 entrapment of lipases in hydrophobic sol−gel materials by Reetz, 260−262 molecular bioimprinting by Braco, 263−265 and salt-mediated activation by Dordick. 266−268 It was also reported that addition of a polar organic solvent such as dimethyl sulfoxide, 269,270 crown ether, 271−276 or some surfactant such as polyoxyethylenealkyl ether 277,278 was effective to improve the reaction rate of lipasecatalyzed reaction in organic solvents. Among these methods, the salt-mediated activation of hydrolase by the Dordick group might be the most unique.…”

Section: Activation Of Lipases By the Il Engineeringmentioning

confidence: 99%

“…Immobilization is very important for increasing the activity of enzymes. − Several landmark methodologies for bringing out the potential of lipase have been developed: lipid coating mediated activation by Okahata, , entrapment of lipases in hydrophobic sol–gel materials by Reetz, − molecular bioimprinting by Braco, − and salt-mediated activation by Dordick. − It was also reported that addition of a polar organic solvent such as dimethyl sulfoxide, , crown ether, − or some surfactant such as polyoxyethylenealkyl ether , was effective to improve the reaction rate of lipase-catalyzed reaction in organic solvents. Among these methods, the salt-mediated activation of hydrolase by the Dordick group might be the most unique. − The authors reported that proteases Subtilisin Carlsberg and α-chymotrypsin could be activated by a large amount of salts with kosmotropic anions by the lyophilization process; reaction rate of the KCl-treated protease mediated alcoholysis reaction was drastically improved and over 3000-fold acceleration was accomplished compared to the native enzyme-catalyzed reaction (Figure ).…”

Section: Enzymes Activated By Ionic Liquids For Organic Synthesismentioning

confidence: 99%

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Ionic Liquids as Tool to Improve Enzymatic Organic Synthesis

2017

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Ionic liquids (ILs) have now been acknowledged as reaction media for biotransformations. The first three examples were reported in this field in 2000, and since then, numerous applications have been reported for biocatalytic reactions using ILs. Two topics using ILs for enzymatic reactions have been reviewed from the standpoint of biocatalyst mediating organic synthesis; the first is "Biocatalysis in Ionic Liquids" which includes various types of biocatalytic reactions in ILs (section 2): (1) recent examples of lipase-mediated reactions using ILs as reaction media for biodiesel oil production and for sugar ester production, (2) oxidase-catalyzed reactions in ILs, (3) laccase-catalyzed reactions, (4) peroxidase-catalyzed reactions, (4) cytochrome-mediated reactions, (5) microbe-mediated hydrations, (6) protease-catalyzed reactions, (8) whole cell mediated asymmetric reduction of ketones, (10) acylase-catalyzed reactions, (11) glycosylation or cellulase-mediated hydrolysis of polysaccharides, (12) hydroxynitrile lyase-catalyzed reaction, (13) fluorinase or haloalkane dehydrogenase-catalyzed reaction, (14) luciferase-catalyzed reactions, and (15) biocatalytic promiscuity of enzymatic reactions for organic synthesis using ILs. The second is "Enzymes Activated by Ionic Liquids for Organic Synthesis", particularly describing the finding story of activation of lipases by the coating with a PEG-substituted IL (section 3). The author's opinion toward "Future Perspectives of Using ILs for Enzymatic Reactions" has also been discussed in section 4.

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Section: Activation Of Lipases By the Il Engineeringmentioning

confidence: 99%

Section: Enzymes Activated By Ionic Liquids For Organic Synthesismentioning

confidence: 99%

Ionic Liquids as Tool to Improve Enzymatic Organic Synthesis

2017

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“…[6][7][8] Asymmetric hydrogen transfer is based on alcohol dehydrogenases that require nicotinamide cofactors, which have the disadvantage of requiring cofactor recycling. 9 The resolution of racemic sec-alcohols via enantioselective hydrolysis of their corresponding esters can be carried out using hydrolases that include lipases from microbial origin 10 and esterases from animal origin, specifically from the liver. 11 Liver acetone powders (LAPs) from different animals were used as crude sources of esterases, 11 which have the advantage of not going through the tedious and expensive process of purification.…”

Section: Introductionmentioning

confidence: 99%

Screening of liver acetone powders in the resolution of 1-phenylethanols and 1-phenylpropanols derivatives

Solı́s

García

Pérez

et al. 2008

Tetrahedron: Asymmetry

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“…The use of microwave irradiation to activate a zirconium-based catalyst has been reported in a few articles. [6][7][8] The work reported in this paper focuses on the application of Zr-based catalysts for a novel route towards the production of nylon-6. [3,4] Selective heating of the catalyst may lead to higher activities and enhanced selectivities.…”

Section: Introductionmentioning

confidence: 99%

A Novel Production Route for Nylon‐6: Aspects of Microwave‐Enhanced Catalysis

Meuldijk

Kruijs

Vekemans

et al. 2011

Macromolecular Symposia

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Summary: Microwave irradiation was used for the amidation of a nitrile with an amine with a freshly prepared zirconium-based heterogeneous catalyst. Microwave irradiation selectively heats the catalyst which enhances its activity as compared to conventional heating. The difference between microwave heating and conventional heating disappears when Zr(OH) 4 is used instead of ZrO 2 , indicating a microwaveinduced shift in the hydrolysis equilibrium, i.e. the distribution of ZrO 2 , ZrO(OH) 2 and Zr(OH) 4 , of the zirconium-based catalyst. The catalyst efficiently catalyzes the amidation of valeronitrile with n-hexylamine with conventional as well as with microwave heating. Zr(OH) 4 was also used for the polymerization of 6-aminocapronitrile using conventional and microwave heating. With both heating methods a relatively low molecular weight polymer with a M n of 4000 g/mol was obtained in a sealed vessel, due to the presence of water and ammonia. A post-polymerization step under microwave irradiation, with active removal of water and ammonia shifts M n to 10000 g/mol. Pressure decrease to facilitate water removal resulted in products with higher molecular weights. A pressure reduction to 50 Pa and operation in an argon atmosphere at 230 8C resulted in nylon-6 with a M n of 65000 in rather short reaction times. Lower pressures led to end-biting and evaporation of the volatile e-caprolactam at 230 8C. As a consequence the resulting product has than a much lower molecular weight. The combination of a heterogeneous zirconium based catalyst and microwave heating is promising for process intensification for nylon-6 production.

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Resolution of racemic 1-arylethyl acetates by Pseudomonas fluorescens in the presence of a surfactant

Cited by 7 publications

References 40 publications

Ionic Liquids as Tool to Improve Enzymatic Organic Synthesis

Ionic Liquids as Tool to Improve Enzymatic Organic Synthesis

Screening of liver acetone powders in the resolution of 1-phenylethanols and 1-phenylpropanols derivatives

A Novel Production Route for Nylon‐6: Aspects of Microwave‐Enhanced Catalysis

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