Regioselective acylation of disaccharides in tert-butyl alcohol catalyzed by Candida antarctica lipase

Oosterom, Marjolein Woudenberg-van; Rantwijk, Fred van; Sheldon, Roger A.

doi:10.1002/(sici)1097-0290(19960205)49:3<328::aid-bit11>3.0.co;2-a

Cited by 144 publications

(48 citation statements)

References 10 publications

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“…With different fatty acids, sucrose gave approximately 40% esterification (40). Using Candida antarctica lipase at elevated temperatures of 40-80°C gave a similar conversion of sucrose after a prolonged reaction time (7 d) (41). With lipase from Mucor miehei as catalyst in a solventfree system, a 25% yield of predominantly 6-O-acyl sucrose was obtained.…”

Section: Regioselective Enzymatic Synthesis Of Fatty Acid Sucrose Estersmentioning

confidence: 94%

Syntheses and applications of sucrose‐based esters

Plat

Linhardt

2001

J Surfact & Detergents

167

105

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Section: Regioselective Enzymatic Synthesis Of Fatty Acid Sucrose Estersmentioning

confidence: 94%

Syntheses and applications of sucrose‐based esters

Plat

Linhardt

2001

J Surfact & Detergents

167

105

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“…Although this analysis indicated that the product was a monolauroyl maltose, it could not be concluded whether the 6-Oor 6-O¢-hydroxyl group of maltose was acylated. Woudenberg-van Oosterom et al (1996) reported that Candida antarctica lipase catalyzed the acylation of only the 6-O¢-hydroxyl group of maltose. As shown later, the residual area per molecule of the product, which was determined from the measurement of the surface tensions of the aqueous solution of the product, suggested acylation of maltose at the 6-O¢-hydroxyl group of maltose.…”

Section: Methodsmentioning

confidence: 99%

“…Much attention has been paid recently to the enzymatic synthesis of the fatty acid esters of mono-and disaccharides due to its regio-and stereoselectivity (Ducret et al, 1996;Woudenberg-van Oosterom et al, 1996). Although some reports on the enzymatic preparation of the fatty acid esters of maltose (Ku & Hang, 1995;Woudenberg-van Oosterom et al, 1996;Degn et al, 1999;Ferrer et al, 2000) have been published, they were performed by a batch reaction on a small scale. In their preparation through the condensation of maltose and a fatty acid, water is produced as a byproduct.…”

mentioning

confidence: 99%

Lipase-Catalyzed Synthesis of Monolauroyl Maltose through Condensation of Maltose and Lauric Acid

Zhang

Kobayashi

Watanabe

et al. 2003

FSTR

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Monolauroyl maltose was synthesized through the immobilized-lipase-catalyzed condensation of maltose and lauric acid in acetone using a batch reactor or a continuous stirred tank reactor. The presence of 4A molecular sieves significantly increased the conversion by the removal of water from the reaction mixture. The surfactant properties of the monolauroyl maltose were measured at different temperatures, and the critical micelle concentration depended little on the temperature.Keywords: monolauroyl maltose, lipase, condensation, surface tension Sucrose fatty acid esters synthesized by conventional chemical methods are widely used as detergents and as additives in foods. It has also been reported that the fatty acid esters of maltose and trehalose show antitumor activity (Kohya et al., 1986;Okabe et al., 1999). Much attention has been paid recently to the enzymatic synthesis of the fatty acid esters of mono-and disaccharides due to its regio-and stereoselectivity (Ducret et al., 1996;Woudenberg-van Oosterom et al., 1996). Although some reports on the enzymatic preparation of the fatty acid esters of maltose (Ku & Hang, 1995;Woudenberg-van Oosterom et al., 1996;Degn et al., 1999;Ferrer et al., 2000) have been published, they were performed by a batch reaction on a small scale. In their preparation through the condensation of maltose and a fatty acid, water is produced as a byproduct. The removal of the water by addition of a desiccant, i.e., molecular sieves, can shift the reaction toward the desired product (Ferrer et al., 2000). However, a detailed examination of the effect of such an addition on the conversion has not been done for the synthesis of maltose fatty acid esters.In this context, we first investigated the effects of the molar ratio of a fatty acid, lauric acid, to maltose and the maltose concentration at a fixed molar ratio on the conversion in the absence and presence of 4A molecular sieves for the synthesis of monolauroyl maltose through the condensation catalyzed by Candida antarctica lipase in acetone using a small-scale batch reactor. The continuous synthesis of monolauroyl maltose was then carried out using a continuous stirred tank reactor (CSTR), and the surfactant properties of the monolauroyl maltose were also examined. Materials and MethodsMaterials Immobilized lipase from Candida antarctica, Chirazyme ® L-2 C2, was purchased from Roche Molecular Biochemicals, Mannheim, Germany. Maltose monohydrate, lauric acid, 4A 1/16 molecular sieves, acetone and all other chemicals were purchased from Wako Pure Chemical Industries, Osaka, Japan.Synthesis of monolauroyl maltose in a batch reaction Prior to use, all the solvents were dehydrated with 4A molecular sieves for at least 24 h. Maltose monohydrate (0.25 to 1.0 mmol), lauric acid (0.25 to 4.0 mmol) and the immobilized lipase (100 mg) were weighed in a glass vial with a screw-cap, and then 5 ml of a solvent was added to the vial. If necessary, the 4A molecular sieves (100 to 500 mg) were put into the vial. The vial was immersed in a water bath at...

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“…286). To use sucrose as an example, lipase from C. antarctica and T. lanuginosa can catalyze esterification at only the 6-and 6′-hydroxyl positions (with a preference toward 6-OH) (292)(293)(294)(295). The use of isopropylidene protective groups to improve substrate miscibility (see foregoing discussion) leads to synthesis of only the 6′ esters since the protective group blocks access to the 6-hydroxyl (296).…”

Section: Fa-based Products Via Enzyme Reactionsmentioning

confidence: 99%

Enzyme‐Catalyzed modification of oilseed materials to produce eco‐friendly products

Hayes

2004

J Americ Oil Chem Soc

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Novel products produced from seed oil materials (TAG, phospholipids, and minor components such as tocopherols, sterols, stanols, and fatty acyl esters of the latter two) by enzyme-mediated purification or chemical modification are reviewed. The primary focus is on "value-added products" of current and potential use (particularly in the food, cosmetics, and pharmaceutical industries) that require the selectivity of enzymes and mild operating conditions, the latter being beneficial for polyunsaturated and oxygenated acyl groups. The paper briefly reviews the biochemistry of enzymes in lipid modification (lipases, phospholipases, and lipoxygenases) and discusses and assesses the current and future applications, current state of the art, and areas for future research for the following enzyme-mediated processes: isolation of polyunsaturated and oxygenated FFA; formation of structured TAG as nutraceuticals; formation of MAG, saccharide-FA esters, and other polyhydric alcohol ester as emulsifiers and surfactants; isolation and/or modification of tocopherols and sterols as antioxidants; formation of hydroperoxides as chemical intermediates; and modification of phospholipids for use in liposomes.Agriculturally derived feedstocks will play an increasingly important role in North America and worldwide as the cost of petroleum continues to increase and its availability decreases. Lipids (TAG, phospholipids, sterols, etc.) are an example of such a feedstock. Although lipids are readily modified by chemical means (reviewed in Refs. 1-5) and can be synthesized from petroleum-based feedstocks (6), there is an increased interest in modifying lipids via biocatalysis, particularly to manufacture lipid-based products in the food, cosmetics, and pharmaceutical industries, and for applications focused on environmental friendliness, due to the mild reaction conditions and narrow product distributions. In addition, biocatalysis has also played a role in isolating natural products, for instance, by temporarily modifying the molecule of interest to facilitate downstream separations. Reviews on biocatalytic modification of lipids have appeared during the last 15 yr (7-11) and more recently in two monographs (12,13). In addition, a recent conference entitled Enzymes in Lipid Modification was held in 2003 in Greifswald, Germany (14). The organization and emphasis of the previous reviews focused mostly on the types of biocatalysts; the emphasis here is on the products formed. Preceding the discussion of products is a brief overview of the important biocatalytic tools to be used. BIOCATALYSTS USED FOR LIPID MODIFICATIONLipases (EC 3.1.1.3). Lipases are specifically designed by nature for the hydrolysis and synthesis of ester bonds involving FA, and can form and/or hydrolyze amide, carbonate, and thioester bonds as well. Reactions catalyzed by lipases that involve the ester bond are diagrammed in Figure 1. Lipases are perhaps the most frequently used enzymes for biotransformations because of their ability to function in nonaqueous and aqueous ...

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Regioselective acylation of disaccharides in tert-butyl alcohol catalyzed by Candida antarctica lipase

Cited by 144 publications

References 10 publications

Syntheses and applications of sucrose‐based esters

Syntheses and applications of sucrose‐based esters

Lipase-Catalyzed Synthesis of Monolauroyl Maltose through Condensation of Maltose and Lauric Acid

Enzyme‐Catalyzed modification of oilseed materials to produce eco‐friendly products

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