Lipase mediated synthesis of sugar fatty acid esters

Gumel, Ahmad Mohammed; Annuar, Mohamad Suffian Mohamad; Heidelberg, Thorsten; Chisti, Yusuf

doi:10.1016/j.procbio.2011.07.021

Cited by 205 publications

(123 citation statements)

References 134 publications

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“…A ratio of 1:5 was better than 1:1 for achieving higher yields: Novozym 73% vs. 6% in 1.5 h; Lipozyme TL IM 43% vs. 23% in 1 h; Lipozyme from Mucor miehei 73% vs. 37% in 5 h. Two factors could be involved in this behaviour: (a) due to the lower concentration of acyl donor in the 1:1 reaction, the low water content present was enough for the vinyl laurate's hydrolysis, and therefore the transesterification reaction to sugar esters decreased [40]; (b) the lactulose monoesters produced, due to their amphiphilic behaviour, could help to avoid sugar precipitation, stabilizing the reaction mixture and displacing the equilibrium of the reaction towards transesterification [41,42]. When the reaction temperature decreased from 60 to 30 °C, the synthesis of monoesters was preferred over diesters synthesis, and the effect could be translated into an increase in selectivity with a lower temperature.…”

Section: Effect Of Substrates Concentrations On Monoesters Yieldmentioning

confidence: 99%

Regioselective Synthesis of Lactulose Esters by Candida antarctica and Thermomyces lanuginosus Lipases

et al. 2017

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Abstract:The interest in sugar esters as emulsifiers has been increasing in recent years because they have tunable surfactant properties that depend on the chain length of the fatty acid and the type of the sugar, covering a wide range of hydrophilic-lipophilic balance (HLB). In this work, ten biocatalysts were used for the transesterification reaction screening of lactulose, a prebiotic sugar, with vinyl laurate. The reactions were followed by thin layer chromatography (TLC) analysis, identifying two major monoesters mixtures defined as monoester fraction 1 and monoester fraction 2. Candida antarctica lipase B (Novozym 435) produces "monoester fraction 1", while Thermomyces lanuginosus lipase (Lipozyme ® TL IM) and Mucor miehei lipase (Lipozyme ® ) seem to produce the same "monoester fraction 2". These three enzymes were selected as model biocatalysts for a kinetic study, and monoester fractions 1 and 2 from Novozym 435 and Lipozyme ® TL IM, respectively, were used for product characterization. Monoester fraction 1 contained 86.9% of the major monoester in position 1-O-, and monoester fraction 2 contained 91.4% of 6 -O-. Although these lipases acylated three positions of lactulose, they mainly synthesize a monoester presenting regioselectivity. These results contribute to the study of the chemical structure diversity of biosurfactants to enhance their applications in foods, pharmaceutical products, and cosmetics.

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Section: Effect Of Substrates Concentrations On Monoesters Yieldmentioning

confidence: 99%

Regioselective Synthesis of Lactulose Esters by Candida antarctica and Thermomyces lanuginosus Lipases

et al. 2017

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“…Wax esters can be used for various applications, such as coatings for wood [4] or as ingredients for cosmetics [5]. Furthermore, fatty acids can be used as the hydrophobic building blocks of surfactants such as carbohydrate esters [6,7]. Still another application is the use of erucic acid and its derivatives, such as erucamide, in manufacturing plastics, nylon13-13 and high temperature lubricants [8].…”

Section: Introductionmentioning

confidence: 99%

Combination of modern plant breeding and enzyme technology to obtain highly enriched erucic acid from Crambe oil

Volkova

Zhu

et al. 2016

Sustain Chem Process

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Background: Fatty acids from vegetable oils are useful building blocks for industrial materials. The purpose of this work was to prepare erucic acid with high purity from a vegetable oil. High purity erucic acid is used for the production of erucamide with applications in plastics manufacturing. A newly developed transgenic Crambe line produces seed oil with 68 % erucic acid compared to 53 % in the wild type oil.Results: Further enrichment of erucic acid from Crambe (wild type and transgenic) oil was achieved by selective enzymatic hydrolysis. Using Candida rugosa lipase as catalyst, other fatty acids were preferentially hydrolysed from the triacylglycerols and erucic acid was enriched in the acylglycerol fraction. The highest content of erucic acid achieved in that fraction was 95 %. Conclusions:The combination of modern plant breeding and enzyme technology is a promising approach for preparation of fatty acids of high purity.

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“…In addition, the combination of high temperature and alkaline catalyst used in chemical processes, causes discoloration of the product and the formation of toxic byproducts. Some of the byproducts are allergenic and possibly carcinogenic [9]. Synthesis can be performed under mild reaction conditions, which are compared to the chemical synthesis to minimize side reactions and the browning of the products.…”

Section: Introductionmentioning

confidence: 99%

The Microwave-assisted Lipase-catalyzed Synthesis of Sucrose Laurate

Li¹,

Xin²,

Yao³

et al. 2016

Advances in Computer Science Research

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Abstract. In this study, the lauroyl sucrose ester was synthesized by microwave-assisted lipase-catalyzed reaction under non-aqueous system. The influence of the microwave power, the amount of molecular sieve added and the reaction time on the conversion of sugar esters were explored. The results showed that compared with conventional heating, microwave-assisted lipase-catalyzed method was short time and can reduce energy consumption. And the thin layer chromatography showed that the lauroyl sucrose ester synthesized by microwave-assisted lipase-catalyzed reaction containing only a single product spot. The optimal conditions was built when the reaction was carried out under 200W of the microwave reaction power and 15 g/L of molecular sieve for 25 min. The maximum conversion of lauroyl sucrose ester was 63.8% under the optimal condition.After three times batch reaction, the residual activity of lipase was 52.4%.

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Lipase mediated synthesis of sugar fatty acid esters

Cited by 205 publications

References 134 publications

Regioselective Synthesis of Lactulose Esters by Candida antarctica and Thermomyces lanuginosus Lipases

Regioselective Synthesis of Lactulose Esters by Candida antarctica and Thermomyces lanuginosus Lipases

Combination of modern plant breeding and enzyme technology to obtain highly enriched erucic acid from Crambe oil

The Microwave-assisted Lipase-catalyzed Synthesis of Sucrose Laurate

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