The effect of ethanol on the kinetics of lipase‐mediated enantioselective esterification of 4‐methyloctanoic acid and the hydrolysis of its ethyl ester

Heinsman, N.W.J.T.; Valente, Angélica Moreira; Smienk, Henry; Padt, A. van der; Franssen, M.C.R.; Groot, Aede de; Riet, K. van ’t

doi:10.1002/bit.10008

Cited by 23 publications

(11 citation statements)

References 20 publications

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“…Inhibition of the alcoholysis reaction by ethanol in the miniplant was surprising. It is even more surprising that the reaction performed well in an acetone/ethanol mixture since this kind of mixture has been said to inactivate lipases [40,41]. The results presented here show that high-yield production of 2-monopalmitate in acetone is possible.…”

Section: Discussionmentioning

confidence: 72%

Highly Efficient Enzymatic Synthesis of 2‐Monoacylglycerides and Structured Lipids and their Production on a Technical Scale

Pfeffer

Freund

Bel-Rhlid

et al. 2007

Lipids

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We report here a two-step process for the high-yield enzymatic synthesis of 2-monoacylglycerides (2-MAG) of saturated as well as unsaturated fatty acids with different chain lengths. The process consists of two steps: first the unselective esterification of fatty acids and glycerol leading to a triacylglyceride followed by an sn1,3-selective alcoholysis reaction yielding 2-monoacylglycerides. Remarkably, both steps can be catalyzed by lipase B from Candida antarctica (CalB). The whole process including esterification and alcoholysis was scaled up in a miniplant to a total volume of 10 l. With this volume, a two-step process catalyzed by CalB for the synthesis of 1,3-oleoyl-2-palmitoylglycerol (OPO) using tripalmitate as starting material was established. On a laboratory scale, we obtained gram quantities of the synthesized 2-monoacylglycerides of polyunsaturated fatty acids such as arachidonic-, docosahexaenoic- and eicosapentaenoic acids and up to 96.4% of the theoretically possible yield with 95% purity. On a technical scale (>100 g of product, >5 l of reaction volume), 97% yield was reached in the esterification and 73% in the alcoholysis and a new promising process for the enzymatic synthesis of OPO was established.

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Section: Discussionmentioning

confidence: 72%

Highly Efficient Enzymatic Synthesis of 2‐Monoacylglycerides and Structured Lipids and their Production on a Technical Scale

Pfeffer

Freund

Bel-Rhlid

et al. 2007

Lipids

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“…This study demonstrates that the HLD‐catalyzed kinetic resolution can be controlled by addition of organic co‐solvents to the reaction media, depending on the enzyme, the solvent, and the substrate. The effect of organic solvents on enzyme enantioselectivity has been already described for various types of biocatalysts, including lipase [11, 72–76], Baeyer‐Villiger monooxygenase [77], alcohol dehydrogenase [78], carbonyl reductase [8], subtilisin Carlsberg [79], and protease [80]. Several mechanisms have been proposed to rationalize the variability of enzyme enantioselectivity in organic solvents: (i) the interference of the co‐solvent molecules with the proper orientation or transformation of one enantiomer more than the other one [81, 82], (ii) the interaction of co‐solvent molecules with the surface of the enzyme or its active site, resulting in conformational alterations [83], (iii) co‐solvent‐induced shift in the racemic temperature [75].…”

Section: Resultsmentioning

confidence: 99%

Organic co‐solvents affect activity, stability and enantioselectivity of haloalkane dehalogenases

Štěpánková

Damborský

Chaloupková

2013

Biotechnology Journal

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Haloalkane dehalogenases are microbial enzymes with a wide range of biotechnological applications, including biocatalysis. The use of organic co-solvents to solubilize their hydrophobic substrates is often necessary. In order to choose the most compatible co-solvent, the effects of 14 co-solvents on activity, stability and enantioselectivity of three model enzymes, DbjA, DhaA, and LinB, were evaluated. All co-solvents caused at high concentration loss of activity and conformational changes. The highest inactivation was induced by tetrahydrofuran, while more hydrophilic co-solvents, such as ethylene glycol and dimethyl sulfoxide, were better tolerated. The effects of co-solvents at low concentration were different for each enzyme-solvent pair. An increase in DbjA activity was induced by the majority of organic co-solvents tested, while activities of DhaA and LinB decreased at comparable concentrations of the same co-solvent. Moreover, a high increase of DbjA enantioselectivity was observed. Ethylene glycol and 1,4-dioxane were shown to have the most positive impact on the enantioselectivity. The favorable influence of these co-solvents on both activity and enantioselectivity makes DbjA suitable for biocatalytic applications. This study represents the first investigation of the effects of organic co-solvents on the biocatalytic performance of haloalkane dehalogenases and will pave the way for their broader use in industrial processes.

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“…Of these 5, only Candida antarctica lipase B (CALB) gave a reasonable reaction rate and selectivity (E = 8 at 45°C). Optimization of the reaction conditions revealed that the best system to resolve 4-methyloctanoic acid in a "food grade" way is a direct esterification with ethanol in a solventless system, at 35°C [6], see Scheme 1.…”

Section: Branched-chain Fatty Acidsmentioning

confidence: 99%

Biocatalytic production of flavors and fragrances

Franssen

Alessandrini

Terraneo

2005

Pure and Applied Chemistry

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The preparation of flavors and fragrances has to be done with great care. When these compounds are meant for consumption, no toxic chemicals are allowed during their preparation. For use in non-food additives, a high purity is required. Both constraints can be easily fulfilled when enzymes are used as catalyst during the production of these compounds. This paper summarizes the work that we have done regarding the preparation of branchedchain fatty acids (sheep flavors) using lipases, the production of glucosides (controlled-release flavors) using glucosidases, the formation of terpene alcohols and grapefruit flavor using enzymes from chicory, and the formation of phenolic antioxidants using lipases.

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The effect of ethanol on the kinetics of lipase‐mediated enantioselective esterification of 4‐methyloctanoic acid and the hydrolysis of its ethyl ester

Cited by 23 publications

References 20 publications

Highly Efficient Enzymatic Synthesis of 2‐Monoacylglycerides and Structured Lipids and their Production on a Technical Scale

Highly Efficient Enzymatic Synthesis of 2‐Monoacylglycerides and Structured Lipids and their Production on a Technical Scale

Organic co‐solvents affect activity, stability and enantioselectivity of haloalkane dehalogenases

Biocatalytic production of flavors and fragrances

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