Lipase-catalyzed esterification of steric hindered fructose derivative by continuous flow and batch conditions

Sutili, Felipe K.; Ruela, Halliny S.; Leite, Selma Gomes Ferreira; Miranda, Leandro Soter de Mariz e; Leal, Ivana Corrêa Ramos; Souza, Rodrigo O. M. A. de

doi:10.1016/j.molcatb.2012.08.004

Cited by 27 publications

(11 citation statements)

References 43 publications

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“…Recently our group reported the lipase catalyzed esterification fructose ketal in high yield 17. The conditions developed on that occasion were chosen as the starting point for the present study, however in the present case the secondary alcohol may turn the substrate reticent to esterification, when compared to the primary alcohol present in the fructose derivative.…”

Section: Resultsmentioning

confidence: 99%

“…In our continuous work on developing continuous flow process for biocatalyzed reactions 17–21, the aim of this work was to develop a continuous flow process using packed bed reactors to investigate the enzymatic esterification of a steric hindered glucose (glucose ketal) with several fatty acids using the immobilized enzyme of Rhizomucor miehei .…”

Section: Introductionmentioning

confidence: 99%

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Lipase‐catalyzed synthesis of secondary glucose esters under continuous flow conditions

Ruela

Sutili

Leal

et al. 2013

Euro J Lipid Sci & Tech

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Chemical methods for the synthesis of sugar esters require the use of high temperatures in the presence of alkaline catalysts resulting in undesirable by-products and low regiosselectivity. Sugar-based fatty acid esters are non-ionic, biodegradable, odorless, non-irritating, non-toxic surfactants widely used pharmaceuticals, cosmetics, detergents, and food industry. Here in we report our results on enzymatic esterification of protected glucose (glucose ketal) with several fatty acids using the immobilized lipase from Rhizomucor miehei under batch and continuous flow conditions, to afford new glucose derivatives with potential surfactant properties. The results presented here shows that high conversions can be obtained in short reaction time.Practical application: The research of new non-toxic, environmentally friendly and biodegradable surfactants to replace chemicals has increased along with the development of green chemistry. Nonionic biosurfactants, such as sugar fatty acid esters, may be obtained by enzymatic synthesis, a simple manufacturing method for application in several areas, including food, cosmetic, detergent, and pharmaceutical industry. In this work we have described the uncommon esterification of a steric hindered secondary hydroxyl group on glucose ketal leading to new glucose derivatives with potential application as surfactants.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Lipase‐catalyzed synthesis of secondary glucose esters under continuous flow conditions

Ruela

Sutili

Leal

et al. 2013

Euro J Lipid Sci & Tech

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“…De Souza research group has published on the use of lipases as synthetic tools for derivatization of organic molecules (Junior et al 2012, Sutili et al 2013, Costa et al 2014. In one example, the group demonstrated that lipases can also catalyze the Michael addition of primary and secondary amines to acrylonitrile (de Souza et al 2009) (Figure 31).…”

Section: Biocatalysismentioning

confidence: 99%

Organic Synthesis: New Vistas in the Brazilian Landscape

Pilli

Assis

2018

An. Acad. Bras. Ciênc.

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In this overview, we present our analysis of the future of organic synthesis in Brazil, a highly innovative and strategic area of research which underpins our social and economical progress. Several different topics (automation, catalysis, green chemistry, scalability, methodological studies and total syntheses) were considered to hold promise for the future advance of chemical sciences in Brazil. In order to put it in perspective, contributions from Brazilian laboratories were selected by the citations received and importance for the field and were benchmarked against some of the most important results disclosed by authors worldwide. The picture that emerged reveals a thriving area of research, with new generations of well-trained and productive chemists engaged particularly in the areas of green chemistry and catalysis. In order to fulfill the promise of delivering more efficient and sustainable processes, an integration of the academic and industrial research agendas is to be expected. On the other hand, academic research in automation of chemical processes, a well established topic of investigation in industrial settings, has just recently began in Brazil and more academic laboratories are lining up to contribute. All these areas of research are expected to enable the future development of the almost unchartered field of scalability.

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“…It has also been demonstrated that sucrose esters (mono-, di-, or tri-esters) are hydrolysed to sucrose and fatty acids prior to intestinal absorption [11,12], giving them a GRAS (Generally Recognized As Safe) status [13]. Although different sugars and acyl donors have been widely studied [1,6,[14][15][16][17], the use of a single sugar with prebiotic properties, such as properties, such as lactulose, has been less studied [18,19] and might open significant applications the food and pharmaceutical fields.…”

Section: Introductionmentioning

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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Lipase-catalyzed esterification of steric hindered fructose derivative by continuous flow and batch conditions

Cited by 27 publications

References 43 publications

Lipase‐catalyzed synthesis of secondary glucose esters under continuous flow conditions

Lipase‐catalyzed synthesis of secondary glucose esters under continuous flow conditions

Organic Synthesis: New Vistas in the Brazilian Landscape

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

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