Lipase-catalyzed synthesis of sucrose monoester: Increased productivity by combining enzyme pretreatment and non-aqueous biphasic medium

Inprakhon, Pranee; Wongthongdee, Natcha; Amornsakchai, Taweechai; Pongtharankul, Thunyarat; Sunintaboon, Panya; Wiemann, Lars O.; Durand, Alain; Sieber, Volker

doi:10.1016/j.jbiotec.2017.07.021

Cited by 25 publications

(14 citation statements)

References 34 publications

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“…The deficiencies associated with the current methods for manufacturing sucrose esters have attracted considerable attention, particularly from academic laboratories. Manifold efforts have been made to improve the current methods of manufacture by focusing on, for example, alternate acyl donors and reaction solvents, , new modes of promoting reaction (including through ultrasonic irradiation), and the use of biological catalysts (enzymes). − The main difficulties encountered in attempts to improve the yields of enzymatic couplings arise from the low activity of the biological catalysts in polar solvents such as DMSO and DMF that are required to dissolve the carbohydrates . To prevent enzyme deactivation it has been suggested that these highly polar solvents are doped with alcoholic ones such as 2-butanol or t -amyl alcohol , that serve as adjuvants.…”

Section: Introductionmentioning

confidence: 99%

Enzymatic Preparation of a Homologous Series of Long-Chain 6-O-Acylglucose Esters and Their Evaluation as Emulsifiers

Liang

Chen

Banwell

et al. 2018

J. Agric. Food Chem.

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Sugar fatty acid esters are nonionic surfactants that are widely exploited in the food and cosmetics industries, as well as in the oral care and medical supply fields. Accordingly, new methods for their selective synthesis and the "tuning" of their emulsifying properties are of considerable interest. Herein we report simple and irreversible enzymatic esterifications of d-glucose with seven fatty acid vinyl esters. The foaming and emulsifying effects of the resulting 6- O-acylglucose esters were then evaluated. In accord with expectations, when the length of the alkyl side chain associated with the 6- O-acylglucose esters increases, then their hydrophilic-lipophilic balance (HLB) values decrease, while the stabilities of the derived emulsions improve. In order to maintain good foaming properties, alkyl side chains of at least 9 to 11 carbons in length are required. In the first such assays on 6- O-acylglucose esters, most of those described herein are shown to be nontoxic to the HepG2, MCF-7, LNacp, SW549, and LO-2 cell lines.

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Section: Introductionmentioning

confidence: 99%

Enzymatic Preparation of a Homologous Series of Long-Chain 6-O-Acylglucose Esters and Their Evaluation as Emulsifiers

Liang

Chen

Banwell

et al. 2018

J. Agric. Food Chem.

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“…While they are of particular utility in the food industry, there are fundamental challenges associated with their manufacture that arise from the presence of eight distinct hydroxyl groups within the carbohydrate core and the ensuing potential for formation of complex product mixtures that include various possible mono-, di-, tri-, and even higher-order esters. , Most of the sucrose esters on the market are currently manufactured by very traditional chemical techniques that involve reactions conducted under harsh conditions and subsequent, tedious purification . The enzymatic synthesis of sucrose esters has garnered considerable interest because of the potential for establishing environmentally benign processes that proceed with high selectivity and so simplifying downstream purification. − Nevertheless, the extensive studies − conducted thus far have revealed some major drawbacks associated with this approach, most notably the low activity of the enzymes in the polar organic solvents required to dissolve the carbohydrates, the relatively long reaction times involved (from 6 h to several days) as well as the low concentrations of the substrate that must be employed (and thus restricting throughput).…”

Section: Introductionmentioning

confidence: 99%

Comparative Study of the Emulsifying Properties of a Homologous Series of Long-Chain 6′-O-Acylmaltose Esters

Banwell

Yan

et al. 2018

J. Agric. Food Chem.

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Emulsifiers derived from renewable resources such as sucrose and fatty acids are high volume commodity chemicals and currently produced by traditional chemical synthesis techniques that lack the capacity to form the most desirable monoesters (of sucrose) in a selective and efficient fashion. The development of new emulsifiers (surfactants) from alternate, structurally simpler but nevertheless abundant disaccharides such as maltose represents a possible solution to this problem. Herein, we report the facile enzymatic preparation of a homologous series of 6'- O-acylmaltose esters and an in-depth evaluation of them revealing that their surfactant properties and thermal stabilities are largely determined by the length of the fatty acid chain. In the first such comparison, we show that the foaming and emulsifying effects of certain of these maltose monoesters are superior to those of their sucrose-derived and commercially exploited counterparts. As such, maltose esters have considerable potential as emulsifiers for use in, for example, the food industry.

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“…The ADS generates the polycyclic core of amorpha-4,11-diene (2) with excellent regio-and stereocontrol; however, its applications remain limited by ADS sensitivity to heat and acidic conditions, as well as the insolubility of 2 in water. Traditional, two-phase systems in batch suffer from low mass transfer due to the minimal area of interface between the two immiscible solvents and from the deactivation of the enzyme through long exposure to organic solvents [121]. As a solution to these limitations, the Allemann and Wirth groups reported the use of several sesquiterpene synthases in segmented flow systems to accelerate mixing and shorten reaction times (Scheme 4) [122].…”

Section: Single-step Flow Biocatalytic Systemsmentioning

confidence: 99%

Flow Biocatalysis: A Challenging Alternative for the Synthesis of APIs and Natural Compounds

Santi

Sancineto

Nascimento

et al. 2021

IJMS

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Biocatalysts represent an efficient, highly selective and greener alternative to metal catalysts in both industry and academia. In the last two decades, the interest in biocatalytic transformations has increased due to an urgent need for more sustainable industrial processes that comply with the principles of green chemistry. Thanks to the recent advances in biotechnologies, protein engineering and the Nobel prize awarded concept of direct enzymatic evolution, the synthetic enzymatic toolbox has expanded significantly. In particular, the implementation of biocatalysts in continuous flow systems has attracted much attention, especially from industry. The advantages of flow chemistry enable biosynthesis to overcome well-known limitations of “classic” enzymatic catalysis, such as time-consuming work-ups and enzyme inhibition, as well as difficult scale-up and process intensifications. Moreover, continuous flow biocatalysis provides access to practical, economical and more sustainable synthetic pathways, an important aspect for the future of pharmaceutical companies if they want to compete in the market while complying with European Medicines Agency (EMA), Food and Drug Administration (FDA) and green chemistry requirements. This review focuses on the most recent advances in the use of flow biocatalysis for the synthesis of active pharmaceutical ingredients (APIs), pharmaceuticals and natural products, and the advantages and limitations are discussed.

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Lipase-catalyzed synthesis of sucrose monoester: Increased productivity by combining enzyme pretreatment and non-aqueous biphasic medium

Cited by 25 publications

References 34 publications

Enzymatic Preparation of a Homologous Series of Long-Chain 6-O-Acylglucose Esters and Their Evaluation as Emulsifiers

Enzymatic Preparation of a Homologous Series of Long-Chain 6-O-Acylglucose Esters and Their Evaluation as Emulsifiers

Comparative Study of the Emulsifying Properties of a Homologous Series of Long-Chain 6′-O-Acylmaltose Esters

Flow Biocatalysis: A Challenging Alternative for the Synthesis of APIs and Natural Compounds

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