Solvent-free kinetic resolution of primary amines catalyzed by Candida antarctica lipase B: effect of immobilization and recycling stability

Päiviö, Mari; Perkiö, Päivi; Kanerva, Liisa T.

doi:10.1016/j.tetasy.2012.02.008

Cited by 40 publications

(20 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Thus, manufacturing processes using solvent‐free systems can adopt a green and environmentally friendly route . Päiviö et al reported that racemic amines were acylated by equimolar amounts of isopropyl methoxyacetate using Candida antarctica lipase B Novozym 435 and sol–gel CAL‐B as catalysts in a solvent‐free system, the conversion and enantiomeric excess of (R)‐ N ‐(1‐phenylethyl)acetamide reached 48% and 97%, respectively …”

Section: Introductionmentioning

confidence: 99%

Continuous enantiomer‐selective acylation reaction of 1‐phenylethanamine in a magnetic fluidized bed reactor system (MFBRS)

Pan

Tang

et al. 2019

J of Chemical Tech & Biotech

View full text Add to dashboard Cite

BACKGROUND Magnetic nanoparticle immobilized enzymes are attractive owing to their potential applications in many biological fields. When an alternating magnetic field is applied, the magnetic moments of the magnetic nanoparticles are apt to align in the direction of the field, and the magnetic nanoparticles experience force in the direction of the field. Thus, the magnetic nanoparticles behave like microscopic stirrers. RESULTS In this study, (R)‐N‐(1‐phenylethyl)acetamide was prepared continuously using immobilized lipase in an alternating magnetic field. The effect of several factors on the acylation reaction were investigated. A kinetic model of the continuous acylation reaction process also was developed. The conversion of 1‐phenylethanamine reached a maximum value of 41.8% with lipase concentration 75 mg mL−1 (dry weight/reaction volume), substrate concentration 500 mmol L−1 and flow rate 25 μL min−1 The enantiomeric excess of (R)‐N‐(1‐phenylethyl)acetamide was > 98.4%. The kinetic constants of the continuous reduction were rm = 2.25 × 10−2 mmol L–1 min−1, kcat = 6 × 10−4 mmol L–1 min−1, KA = 0.75 mmol L–1 , KB = 4.36 × 10−3, KQA = 2.43 × 10−2 and KBQA = 6.2 × 10−4 mmol L–1. The kinetic model was in good agreement with the experimental data obtained during continuous acylation reaction. CONCLUSION The results revealed that the inhibition of the acylation reaction at high substrate concentrations was eliminated during the continuous reaction. Compared with the batch acylation reaction, the continuous acylation reaction showed significantly improved lipase catalyst efficiency. © 2019 Society of Chemical Industry

show abstract

Section: Introductionmentioning

confidence: 99%

Continuous enantiomer‐selective acylation reaction of 1‐phenylethanamine in a magnetic fluidized bed reactor system (MFBRS)

Pan

Tang

et al. 2019

J of Chemical Tech & Biotech

View full text Add to dashboard Cite

show abstract

“…The authors also carried out solution reactions in 2 mL of dioxane at 55 or 80 °C, which were shown to lead to lower conversion and enantiomeric excess. Furthermore, a non‐mechanochemical solvent‐free approach developed by Kanerva and co‐workers, which involves reacting 2 mmol of rac ‐ 4 a with one equivalent of isopropyl acetate (IPrA) in the presence of 25 mg of immobilized CALB, led only to 7–10 % conversion of ( R )‐ 5 a , when incubated in a shaker at 170 rpm for 6 hours . Acetylation proceeded to 50 % conversion however when either isopropyl or ethyl methoxyacetate was used as the acyl donor .…”

Section: Lipase‐catalyzed Mechanoenzymatic Reactions By Ball Milling mentioning

confidence: 99%

“…Furthermore, a non‐mechanochemical solvent‐free approach developed by Kanerva and co‐workers, which involves reacting 2 mmol of rac ‐ 4 a with one equivalent of isopropyl acetate (IPrA) in the presence of 25 mg of immobilized CALB, led only to 7–10 % conversion of ( R )‐ 5 a , when incubated in a shaker at 170 rpm for 6 hours . Acetylation proceeded to 50 % conversion however when either isopropyl or ethyl methoxyacetate was used as the acyl donor . Systematic studies comparing solvent‐free reactions induced by milling, shaking and stirring at equal enzyme loading with a variety of amines would be valuable in determining differences between these approaches.…”

Section: Lipase‐catalyzed Mechanoenzymatic Reactions By Ball Milling mentioning

confidence: 99%

Mechanoenzymatic Transformations in the Absence of Bulk Water: A More Natural Way of Using Enzymes

2019

View full text Add to dashboard Cite

Mechanochemical enzymatic reactions without bulk water have emerged as a low‐waste and efficient method to access useful chemicals and to depolymerize biomass components in a single step. This emergent mechanoenzymatic reaction strategy is able to take advantage of the stereospecificity, regio‐ and stereoselectivity, as well as renewability of enzymes, while avoiding bulk solvents, offering the opportunity to control the direction of the reaction, bypassing reactant solubility issues, and enabling reactions with water‐sensitive substrates or products. Enzymes are traditionally used in dilute aqueous solution, which is quite different from their crowded, water‐depleted natural environment. This review outlines recent work which demonstrates that enzymes can be equally or even more efficient under mechanochemical conditions, without bulk aqueous or organic solvent.

show abstract

“…Most of the kinetic resolutions of racemic amines with CaLB were run in organic solvents [3][4][5][6] or even under neat, solvent free conditions. 7 Recently, dynamic-kinetic resolution methods using CaLB have been reported, 8 to give much better conversion than simple kinetic resolutions. CaLB biocatalyst is suitable for the N-acylation of a wide range of aromatic and aliphatic amines even under continuous-flow conditions.…”

Section: Introductionmentioning

confidence: 99%

“…6 Several acylating agents can be used for lipase-catalyzed stereoselective biotransformations. For example esters, such as ethyl acetate, 6 isopropyl acetate, 7 isopropyl butanoate, isopropyl methoxyacetate 7,9 or acids, such as myristic acid 10 may be useful. The kinetic resolution of 1-phenylethanamine and other amines with lipases and ethyl methoxyacetate 11,12 has been applied on an industrial scale by BASF since 1993.…”

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic route to Tyrphostins involving lipase-catalyzed kinetic resolution of 1-phenylethanamine with alkyl cyanoacetates as novel acylating agents

Csuka

Boros

Őrfi

et al. 2015

Tetrahedron: Asymmetry

View full text Add to dashboard Cite

Solvent-free kinetic resolution of primary amines catalyzed by Candida antarctica lipase B: effect of immobilization and recycling stability

Cited by 40 publications

References 33 publications

Continuous enantiomer‐selective acylation reaction of 1‐phenylethanamine in a magnetic fluidized bed reactor system (MFBRS)

Continuous enantiomer‐selective acylation reaction of 1‐phenylethanamine in a magnetic fluidized bed reactor system (MFBRS)

Mechanoenzymatic Transformations in the Absence of Bulk Water: A More Natural Way of Using Enzymes

Chemoenzymatic route to Tyrphostins involving lipase-catalyzed kinetic resolution of 1-phenylethanamine with alkyl cyanoacetates as novel acylating agents

Contact Info

Product

Resources

About