Selectivity of fatty acid incorporation into acylglycerols in esterification reactions using Rhizomucor miehei and Burkholderia cepacia lipases

Fu, Xun; Parkin, Kirk L.

doi:10.1016/j.foodres.2004.02.008

Cited by 12 publications

(9 citation statements)

References 21 publications

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“…This observation also revealed that Lipozyme RM IM has higher selectivity towards long-chain fatty acid and showed a preferential incorporation of oleic acid rather than capric acid into the TAG pool during the esterification reaction. A similar observation was also reported in the work of Fu and Parkin (2004).…”

Section: Resultssupporting

confidence: 91%

“…Acyl migration may occur between these two steps and results in the formation of by-products that may affect product quality (Mu et al 2001;Kawashima et al 2004;Kim and Akoh 2005). On the contrary, migration of the acyl groups from positions 1 or 3 to 2 is necessary for the TAG formation in the lipase-catalyzed esterification synthesis as Lipozyme RM IM used to esterify glycerol is a 1, 3-specific lipase (Fu and Parkin 2004). Therefore, isomerization reaction is the limiting step for TAG synthesis.…”

Section: Introductionmentioning

confidence: 99%

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Enzymatic Synthesis of Medium- and Long-Chain Triacylglycerols (MLCT): Optimization of Process Parameters Using Response Surface Methodology

Koh

Tan

Lai

et al. 2008

Food Bioprocess Technol

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The main objective of this study was to understand the effects and relationship amongst four factors, which are reaction temperature, reaction time, enzyme load, and substrate mole ratio with the purpose of producing healthy functional cooking oil for long-term dietary treatment. Lipozyme RM IM lipase-catalyzed esterification of medium-and long-chain triacylglycerols (MLCT) from glycerol and mixtures of capric and oleic acid was optimized using response surface methodology (RSM) with a fivelevel, four-factorial design. Reaction temperature, reaction time, and substrate mole ratio strongly affected MLCT synthesis (P<0.01). However, enzyme load did not have a significant (P>0.01) effect on MLCT yield. Comparison between predicted and experimental value from central composite rotatable design optimization procedures revealed good correlation, implying that the reduced cubic polynomial model with backward elimination statistically expressed the percent MLCT yield obtained. The optimum MLCT yield was 59.76% by using 10 wt% enzyme load, reaction temperature of 70°C, reaction time of 14 h, and substrate mole ratio of 3.5:1. Experiments to confirm the predicted results using the optimal parameters showed an MLCT yield of 56.35% (n=2). The choice on the types of fatty acids used in MLCT optimization work greatly influenced the physical and chemical properties of MLCT oil produced. The refined MLCT oil characteristics study showed this oil is suitable to be used for cooking/frying purposes as a high-value added product.

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Section: Resultssupporting

confidence: 91%

Section: Introductionmentioning

confidence: 99%

Enzymatic Synthesis of Medium- and Long-Chain Triacylglycerols (MLCT): Optimization of Process Parameters Using Response Surface Methodology

Koh

Tan

Lai

et al. 2008

Food Bioprocess Technol

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show abstract

“…The selectivity of BCL toward fatty acids of different chain length during the synthesis of acylglycerides has been studied by several authors (Chang, Lee, & Parkin, ; Fu & Parkin, ; Lee & Parkin, ). In their report, Chang et al () evaluated the selectivity of BCL in the esterification reaction of glycerol (and glycerol analogues) with fatty acids of a chain length in the range C4–C16 (Table ).…”

Section: Synthesis and Modification Of Glyceridesmentioning

confidence: 99%

Burkholderia cepacia lipase: A versatile catalyst in synthesis reactions

Sánchez

Tonetto

Ferreira

2017

Biotech & Bioengineering

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The lipase from Burkholderia cepacia, formerly known as Pseudomonas cepacia lipase, is a commercial enzyme in both soluble and immobilized forms widely recognized for its thermal resistance and tolerance to a large number of solvents and short-chain alcohols. The main applications of this lipase are in transesterification reactions and in the synthesis of drugs (because of the properties mentioned above). This review intends to show the features of this enzyme and some of the most relevant aspects of its use in different synthesis reactions. Also, different immobilization techniques together with the effect of various compounds on lipase activity are presented. This lipase shows important advantages over other lipases, especially in reaction media including solvents or reactions involving short-chain alcohols.

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“…1, and data were calculated after 24 h of reaction time suggesting C8:0 is preferentially incorporated into PPPenriched TAG. It is reported that Lipozyme RM IM showed a 1.18-fold specificity for incorporation of C8:0 into a TAG over that of C18:1 n-9 [21]. For C18 FA (C18:1 n-9, C18:2 n-6 and C18:3 n-3) examined, crude CBD-T1 lipase showed a strong preference for C18:2 n-6 and C18:3 n-3 over C18:1 n-9.…”

Section: Typoselectivity Of Crude Cbd-t1 Lipasementioning

confidence: 99%

Typoselectivity of CrudeGeobacillussp. T1 Lipase Fused with a Cellulose‐Binding Domain and Its Use in the Synthesis of Structured Lipids

Qin

Huang

Lan

et al. 2013

J Americ Oil Chem Soc

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Typoselectivity of crude CBD-T1 lipase (Geobacillus sp. T1 lipase fused with a cellulose binding domain) was investigated. Multi-competitive reaction mixtures including a set of n-chain fatty acids (C8:0, C10:0, C12:0, C14:0, C18:1 n-9, C18:2 n-6 and C18:3 n-3) and tripalmitin-enriched triacylglycerols were studied in hexane. The crude CBD-T1 lipase discriminated strongly against C18:1 n-9 [competitive factor (a) = 0.23] and showed the highest preference for C8:0 (a = 1). Utilizing the catalytic properties of crude CBD-T1 lipase, acidolysis of soybean oil with C8:0 was selected as a model reaction to investigate the ability of the lipase to produce MLMtype (medium-long-medium) structured lipids. Several reaction parameters (added water amount, reaction temperature, substrate molar ratio and reaction time) examined for incorporating C8:0 into soybean oil, the optimum conditions were: 1:3 (soybean oil/C8:0) of molar ratio, 3 mL of hexane, 50°C of temperature, 48 h of reaction time, 20 % of crude CBD-T1 lipase (w/w total substrates), and 7.5 % of water (w/w enzyme). Under these conditions, the incorporation of C8:0 was 29.6 mol%. The results suggest that crude CBD-T1 lipase, which showed different fatty acid specificity profiles, is a potential biocatalyst for the modification of fats and oils.

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Selectivity of fatty acid incorporation into acylglycerols in esterification reactions using Rhizomucor miehei and Burkholderia cepacia lipases

Cited by 12 publications

References 21 publications

Enzymatic Synthesis of Medium- and Long-Chain Triacylglycerols (MLCT): Optimization of Process Parameters Using Response Surface Methodology

Enzymatic Synthesis of Medium- and Long-Chain Triacylglycerols (MLCT): Optimization of Process Parameters Using Response Surface Methodology

Burkholderia cepacia lipase: A versatile catalyst in synthesis reactions

Typoselectivity of CrudeGeobacillussp. T1 Lipase Fused with a Cellulose‐Binding Domain and Its Use in the Synthesis of Structured Lipids

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