Bridging the bridge—Stabilization of CalB against H2O2 and its application in epoxidation reactions

Steinhagen, Max; Gräbner, Anna; Meyer, Janine; Horst, Andréa; Drews, Anja; Holtmann, Dirk; Ansorge‐Schumacher, Marion B.

doi:10.1016/j.molcatb.2017.01.002

Cited by 10 publications

(13 citation statements)

References 47 publications

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“…While all resins evaluated could immobilize the enzyme in an active form, the performance of Purolite ECR8806 (octadecyl methacylate) was exceptional with an esterification activity of 459.98 U/g, and a specific activity of 23.40 U/mg. The higher activity of lipase immobilized on octadecyl resin is consistent with very recent studies (Steinhagen et al, ). Therefore, lipase PCL immobilized on Purolite ECR8806 was used for all further experiments.…”

Section: Resultssupporting

confidence: 92%

Production and immobilization of lipase PCL and its application in synthesis of α-linolenic acid-rich diacylglycerol

Liu

Wang

et al. 2018

J Food Biochem

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α‐Linolenic acid‐rich diacylglycerol has been demonstrated with promising health promotion functions. This study examined the production, immobilization of lipase PCL, and its application in the synthesis of diacylglycerol by esterification of α‐linolenic acid with glycerol. The resin ECR8806 was selected as an effective support for the immobilization of lipase PCL. Fourier transform infrared and Laser scanning confocal microscope analysis proved that the lipase was successfully immobilized on the resin. Compared with the free PCL, the immobilized one exhibited higher temperature tolerance. Under optimized reaction conditions, a DAG content of 54.49% were obtained. After further purified by molecular distillation, the purity of DAG was up to 99.28%. During esterification, the immobilized PCL was quite stable and retained more than 91.60% of its initial activity after 10 cycles. These new findings on the immobilized PCL will make it to be a prospective enzyme in oils and fats industry. Practical applications Immobilized PCL, a monoacylglycerol and diacylglycerol lipase, was first employed to synthesis of a high purity α‐linolenic acid‐rich diacylglycerol. The improved biocatalytic performance and reusability of the lipase make it to be a promising catalyst in industrial application.

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Section: Resultssupporting

confidence: 92%

Production and immobilization of lipase PCL and its application in synthesis of α-linolenic acid-rich diacylglycerol

Liu

Wang

et al. 2018

J Food Biochem

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“…However, high oxidant concentrations are required for high reaction rates and yields [29]. Attempts to improve lipase stability include adsorptive or covalent carrier binding or molecular crosslinking [30][31][32] as well as immobilization either in organic-modified clay or smectite nanoclay [33,34]. In other approaches, the H 2 O 2 concentration was maintained at low levels by a stepwise addition [13,26,35,36] or replacement by urea-H 2 O 2 [37].…”

Section: Nomenclature Latin Symbolsmentioning

confidence: 99%

“…Fundamentals of the chemo-enzymatic epoxidation and dynamic modeling 23 Balances. The basis for any reactor calculation is the conservation of matter (mass or moles) and of energy [26,31]. For any molecular species i, the molar mass balance is…”

Section: Concentration-time Profilesmentioning

confidence: 99%

“…High enzyme costs are one reason for the chemo-enzymatic epoxidation not yet having been established at large scale [131]. Attempts to improve lipase stability include adsorptive or covalent carrier binding or molecular crosslinking [30][31][32] as well as immobilization either in organic-modified clay or smectite nanoclay [33,34].…”

Section: Chemo-enzymatic Epoxidationmentioning

confidence: 99%

“…To achieve a substrate/enzyme ratio (N H 2 O 2 m -1 CalB ) of 0.13 mol g -1 [31], 3.5 mg of CalB immo were used in the batch experiments. 2 mL standard tubes were placed on a thermoshaker (n=1400 min -1 , Eppendorf thermomixer comfort, Eppendorf GmbH, Germany).…”

Section: Batchmentioning

confidence: 99%

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Produktion von Peroxyoktansäure mittels immobilisierter CalB: Realisierbarkeitsstudie im einphasigen Stoffsystem mit graduellem Wasserstoffperoxid‐Dosing

Meyer

Horst

Steinhagen

et al. 2016

Chemie Ingenieur Technik

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Lipase‐Mediated Conversion of Protecting Group Silyl Ethers: An Unspecific Side Reaction

Pick,

Wenzlaff,

Yousefi

et al. 2023

ChemBioChem

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Silyl ether protecting groups are important tools in organic synthesis, ensuring selective reactions of hydroxyl functional groups. Enantiospecific formation or cleavage could simultaneously enable the resolution of racemic mixtures and thus significantly increase the efficiency of complex synthetic pathways. Based on reports that lipases, which today are already particularly important tools in chemical synthesis, can catalyze the enantiospecific turnover of trimethylsilanol (TMS)‐protected alcohols, the goal of this study was to determine the conditions under which such a catalysis occurs. Through detailed experimental and mechanistic investigation, we demonstrated that although lipases mediate the turnover of TMS‐protected alcohols, this occurs independently of the known catalytic triad, as this is unable to stabilize a tetrahedral intermediate. The reaction is essentially non‐specific and therefore most likely completely independent of the active site. This rules out lipases as catalysts for the resolution of racemic mixtures of alcohols through protection or deprotection with silyl groups.

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Bridging the bridge—Stabilization of CalB against H2O2 and its application in epoxidation reactions

Cited by 10 publications

References 47 publications

Production and immobilization of lipase PCL and its application in synthesis of α-linolenic acid-rich diacylglycerol

Production and immobilization of lipase PCL and its application in synthesis of α-linolenic acid-rich diacylglycerol

Produktion von Peroxyoktansäure mittels immobilisierter CalB: Realisierbarkeitsstudie im einphasigen Stoffsystem mit graduellem Wasserstoffperoxid‐Dosing

Lipase‐Mediated Conversion of Protecting Group Silyl Ethers: An Unspecific Side Reaction

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