Enzymatic Synthesis of Thioesters in Non-conventional Solvents

Caussette, Mylène; Marty, Alain; Combes, Didier

doi:10.1002/(sici)1097-4660(199703)68:3<257::aid-jctb619>3.0.co;2-m

Cited by 27 publications

(15 citation statements)

References 3 publications

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“…The percentage of yields increased with increase in amount of enzyme up to 194 mg. At this point, all substrates are bound to the enzyme and addition of any enzyme molecule may cause a decrease in the yield due to the substrate limitations [28]. However, high amount of enzyme may cause diffusion which relates to mass transfer limitation [29]. Figure 7 represents the effect of varying molar ratio (octyl alcohol/adipic acid) on the synthesis of dioctyl adipate at 50°C, 195 min, and 200.5-mg enzyme.…”

Section: Resultsmentioning

confidence: 99%

Application of Artificial Neural Network for Yield Prediction of Lipase-Catalyzed Synthesis of Dioctyl Adipate

Rahman

Chaibakhsh

Basri

et al. 2009

Appl Biochem Biotechnol

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In this study, an artificial neural network (ANN) trained by backpropagation algorithm, Levenberg-Marquadart, was applied to predict the yield of enzymatic synthesis of dioctyl adipate. Immobilized Candida antarctica lipase B was used as a biocatalyst for the reaction. Temperature, time, amount of enzyme, and substrate molar ratio were the four input variables. After evaluating various ANN configurations, the best network was composed of seven hidden nodes using a hyperbolic tangent sigmoid transfer function. The correlation coefficient (R2) and mean absolute error (MAE) values between the actual and predicted responses were determined as 0.9998 and 0.0966 for training set and 0.9241 and 1.9439 for validating dataset. A simulation test with a testing dataset showed that the MAE was low and R2 was close to 1. These results imply the good generalization of the developed model and its capability to predict the reaction yield. Comparison of the performance of radial basis network with the developed models showed that radial basis function was more accurate but its performance was poor when tested with unseen data. In further part of the study, the feedforward backpropagation model was used for prediction of the ester yield within the given range of the main parameters.

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Section: Resultsmentioning

confidence: 99%

Application of Artificial Neural Network for Yield Prediction of Lipase-Catalyzed Synthesis of Dioctyl Adipate

Rahman

Chaibakhsh

Basri

et al. 2009

Appl Biochem Biotechnol

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“…In addition to alkyl esters, it has been demonstrated that two immobilised fungal lipases (Lipozyme TM and Novozyme TM ) can catalyse the synthesis of thioesters from a carboxylic acid and a thiol (thioesterification) and from an ester and a thiol (transthioesterification) in low-water systems (Cavaille-Lefebvre & Combes, 1997; Caussette, Marty, & Combes, 1997). These findings suggest that lipases may play a role in the biosynthesis of flavour thioesters in dairy systems, provided that the key precursors, thiols (e.g., methanethiol) and fatty acids, are available in sufficient amounts and that the water activity is favourable (see Section 4.2).…”

Section: Article In Pressmentioning

confidence: 99%

Esters and their biosynthesis in fermented dairy products: a review

Liu

Holland

Crow

2004

International Dairy Journal

330

269

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“…Thus, lipase-catalyzed reactions in SCCO 2 have been carried out for such reactions as hydrolysis of tripalmitin (5) and canola oil (6); alcoholysis of cod liver oil (7) and palm kernel oil (8); glycerolysis of soybean oil (9); synthesis of oleoyloleate from oleic acid (10)(11)(12); acylation of glucose with lauric acid (13); thioesterification between oleic acid and butanethiol (14); transesterifications of milk fat with canola oil (15); tristearin with palm oil (16); palm oil with stearic acid (SA) (17); triolein with ethyl behenate and behenic acid (18,19); triolein with SA (20) and propyl acetate with geraniol (21); and randomization of fat and oils (22).…”

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confidence: 99%

Lipase‐catalyzed esterification of stearic acid with ethanol, and hydrolysis of ethyl stearate, near the critical point in supercritical carbon dioxide

Nakaya

Nakamura

Miyawaki

2002

J Americ Oil Chem Soc

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The effect of pressure on the lipase-catalyzed reaction in supercritical carbon dioxide (SCCO 2 ) was investigated for the esterification of stearic acid (SA) with ethanol and the hydrolysis of ethyl stearate (ES) near the critical point, ranging from 6 to 20 MPa in pressure and 35 to 60°C in temperature. The esterification rate of SA began to increase near the critical point and kept increasing steadily with an increase in pressure, reflecting the increase in SA solubility in SCCO 2 . The hydrolysis rate of ES showed a maximum at a pressure near the critical point. When the reaction was carried out with an initial overall ES concentration below its solubility limit in SCCO 2 , the maximum pressure shifted along the extended line of the gas-liquid equilibrium in the supercritical region in the pressure-temperature phase plane. This seems to be related to the singular behavior of some properties in SCCO 2 along this line reported in the literature. These results show the importance of pressure, as well as temperature, as a parameter to control enzyme reactions in SCCO 2 .

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Enzymatic Synthesis of Thioesters in Non-conventional Solvents

Cited by 27 publications

References 3 publications

Application of Artificial Neural Network for Yield Prediction of Lipase-Catalyzed Synthesis of Dioctyl Adipate

Application of Artificial Neural Network for Yield Prediction of Lipase-Catalyzed Synthesis of Dioctyl Adipate

Esters and their biosynthesis in fermented dairy products: a review

Lipase‐catalyzed esterification of stearic acid with ethanol, and hydrolysis of ethyl stearate, near the critical point in supercritical carbon dioxide

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