Lipase-Catalyzed Solid Phase Synthesis of Sugar Fatty Acid Esters

Cao, Linqiu; Fischer, Andreas; Bornscheuer, Uwe T.; Schmid, Rolf D.

doi:10.3109/10242429609110280

Cited by 128 publications

(75 citation statements)

References 21 publications

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“…The low ratio of solvent to sugar which was used in this work reflects recognition of the toxicological implications of the use of organic solvents in the manufacture of food products. As in the case for procedures recently reported for the monoesterification of aldoses and/or sorbitol (Cao et al, 1997;Ljunger et al, 1994;Arcos, 1996;Arcos et al, 1998), the approach presented here for the production of sorbitol diesters is not constrained by solubility considerations. In the experiments corresponding to quantitative production of dicapryloyl (Fig.…”

Section: Discussionmentioning

confidence: 93%

“…While the literature contains some reports of the enzymatic production of monoesters of sorbitol (Ducret et al, 1995;Cao et al, 1997;Chopineau et al, 1988), a technique for quantitative enzymatic synthesis of sorbitol diesters has not previously been proposed. The calculated values of HLB (Table III) are similar to those for the corresponding monoacyl glycerols.…”

Section: Discussionmentioning

confidence: 99%

“…Esterification of sorbitol in 2M2B produces quantitative yields of the monoester with a conversion of 98.4% (Ducret et al, 1995). More recently, procedures have been described for obtaining nearly complete conversion of glucose (Ljunger et al, 1994) and sorbitol (Cao et al, 1997) in a reaction medium where most of the precursor sugar is not dissolved. Methods based on formation of phenylboronic complexes with sugars (Schlotterbeck et al, 1993) containing single free primary hydroxyl group may be exploited for selective monoacylation reactions in apolar media such as n-heptane (Oguntimein et al, 1993;Scheckermann et al, 1995).…”

Section: Introductionmentioning

confidence: 99%

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Quantitative enzymatic production of 1,6‐diacyl sorbitol esters

Arcos

Bernabé

Otero

1998

Biotech & Bioengineering

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Section: Discussionmentioning

confidence: 93%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Quantitative enzymatic production of 1,6‐diacyl sorbitol esters

Arcos

Bernabé

Otero

1998

Biotech & Bioengineering

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“…It has previously been shown that the solvation of the acyl donor can affect the kinetics of lipase-catalyzed esterification reactions (Janssen et al, 1999). Cao et al (1996) reported a significant yield of palmityl glucose in a solid phase esterification with CAL-B and with acetonitrile as adjuvant but only after 96 h of incubation at 60°C.…”

Section: Reaction Mixtures Containing a Single Solventmentioning

confidence: 99%

Optimization of carbohydrate fatty acid ester synthesis in organic media by a lipase from Candida antarctica

Degn

Zimmermann

2001

Biotech & Bioengineering

138

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The effect of solvents and solvent mixtures on the synthesis of myristic acid esters of different carbohydrates with an immobilized lipase from C. antarctica was investigated. The rate of myristyl glucose synthesized by the enzyme was increased from 3.7 to 20.2 micromol min(-1) g(-1) by changing the solvent from pure tert-butanol to a mixture of tert-butanol:pyridine (55:45 v/v), by increasing the temperature from 45 degrees C to 60 degrees C, and by optimizing the relative amounts of glucose, myristic acid, and the enzyme preparation. Addition of more than 2% DMSO to the tert-butanol:pyridine system resulted in a reduction of enzyme activity. Lowering the water content of the enzyme preparation below 0.85% (w/w) resulted in significant decreases in enzyme activity, while increasing the water content up to 2.17% (w/w) did not significantly affect the enzyme activity. The highest yields of myristyl glucose were obtained when an excess of unsolubilized glucose was present in the reaction system. In this case, all of the initially solubilized and a significant amount of the initially unsolubilized glucose was converted to the ester within 24 h of incubation, resulting in a myristyl glucose concentration of 34 mg/mL(-1). Myristic acid esters of fructose (22.3 micromol min(-1) g(-1)), alpha-D-methyl-glucopyranoside (26.9 micromol min(-1) g(-1)) and maltose (1.9 micromol min(-1) g(-1)) could also be prepared using the tert-butanol:pyridine solvent system. No synthesis activity was observed with maltotriose, cellobiose, sucrose, and lactose as substrate.

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“…The reaction media are apolar organic solvent with low water content to avoid hydrolytic side reactions. While successful enzymatic synthesis of esters of mono and disaccharides has been reported in a large number of cases [4][5][6][7], esterification of longer carbohydrates is very difficult to achieve [7]. However, acylation of maltotriose was achieved using vinyl esters as acyl donors and 2-methyl-2-butanol/dimethyl sulfoxide as solvent [8].…”

Section: Introductionmentioning

confidence: 99%

Two-step process for preparation of oligosaccharide propionates and acrylates using lipase and Cyclodextrin Glycosyl Transferase (CGTase)

Ayres

Valença

Franco

et al. 2014

Sustain Chem Process

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Background: Oligosaccharide esters are attractive candidates for applications as surfactants, hydrogels and other materials, but direct enzymatic acylation is difficult with carbohydrates longer than disaccharides. Results: A combination of one lipase-catalyzed step and one transglycosylation step catalyzed by a cyclodextrin glycosyl transferase (CGTase) was used to synthesize oligosaccharide esters. The conversion of glucose and maltose with vinyl propionate catalyzed by Candida antarctica lipase B (Novozym 435) in dioxane proceeded to full conversion to mixtures of mono and diesters. When ethyl acrylate was used as acyl donor, mono and diesters were formed, but full conversion was not reached. The CGTase catalyzed reactions between the glucose and maltose esters and α-cyclodextrin were carried out in water. In the initial phase, addition of the glucose residues of the cyclodextrin to the ester substrate occurred (coupling reaction), followed by disproportionation reactions yielding a range of oligosaccharide esters with varying chain length. The monoesters were efficient acceptors in the CGTase-catalyzed reactions, while the diesters were not converted to a significant extent. As a consequence, the glucose propionate which contained large amounts of diesters was converted to 40% conversion while the maltose propionate which contained mainly monoesters was converted to 86% conversion. Conclusions: A two-step enzymatic process for preparation of oligosaccharide esters has been developed. Oligosaccharide propionates were produced in high yield with a total reaction time of 5 h. The double bond of the acrylate moiety reduced the reaction rate of the lipase catalyzed transesterification, but in both cases, the CGTase efficiently converted the monoesters to oligosaccharide esters.

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Lipase-Catalyzed Solid Phase Synthesis of Sugar Fatty Acid Esters

Cited by 128 publications

References 21 publications

Quantitative enzymatic production of 1,6‐diacyl sorbitol esters

Quantitative enzymatic production of 1,6‐diacyl sorbitol esters

Optimization of carbohydrate fatty acid ester synthesis in organic media by a lipase from Candida antarctica

Two-step process for preparation of oligosaccharide propionates and acrylates using lipase and Cyclodextrin Glycosyl Transferase (CGTase)

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