Fructose Caprylate Biosynthesis in a Solvent-free Medium

An α‐hydroxy acid derivative, α‐butylglucoside lactate, was successfully prepared by enzymatic transesterification of α‐butylglucoside with a lactate alkyl ester in a non‐aqueous medium using immobilized lipase as biocatalyst. Ester synthesis in organic solvent was optimized. Solvent choice was made on the basis of substrate solubility and enzyme stability in the medium. A solvent‐free reaction using butyllactate as lactate donor led to the highest yields. In the presence of 0.5M αbutylglucoside and 100 g/L Novozym®, a 67 % yield could be obtained within 40 h at 50°C. However, the presence of butanol by‐product limited the reaction to a maximum that could not be exceeded in closed systems. The elimination of the alcohol under reduced pressure resulted in the complete equilibrium shift of the transesterification reaction in favor of synthesis; below 15 mbars, more than 95% of 0.5M α‐butylglucoside could be converted within 30 h. Moreover, simultaneous evaporation of water allowed hydrolysis of butyllactate to be eliminated. Consequently, a very high α‐butylglucoside lactate concentration (170 g/) could be obtained in a single batch reaction. A single purification procedure, consisting of butyllactate extraction with hexane, enabled the product to be obtained at a purity above 95% (w/w). 1H and 13C NMR analysis later demonstrated that lactic acid was exclusively grafted onto the primary hydroxyl group of αbutylglucoside. © 1999 John Wiley & Sons, Inc. Biotechnol Bioeng 62: 225–234, 1999.

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Enzymatic synthesis of unsaturated fatty acid glucoside esters for dermo-cosmetic applications

Bousquet

Willemot

Monsan

et al. 1999

Biotechnol. Bioeng.

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Unsaturated fatty acid α‐butylglucoside esters were prepared by enzymatic esterification of α‐butylglucoside in nonaqueous media. Conditions were firstly optimized using oleic acid as acyl group. Synthesis was possible in several solvents but the presence of water co‐product in the medium limited the reaction to a thermodynamic equilibrium corresponding to a maximal conversion yield of 62%. In pure molten substrates, the removal of water under reduced pressure enabled yields superior to 95% to be obtained. Product profiles depended on enzyme origin : whatever the support, immobilized lipase B from Candida antarctica proved to be far more regioselective for the primary hydroxyl group of glucose than immobilized lipase from Rhizomucor miehei. Results obtained could be easily transposed to the acylation of α‐butylglucoside with a commercial mixture of unsaturated fatty acids containing more than 60% of linoleic acid. The biocatalyst could be recycled more than ten times without any significant activity loss. © 1999 John Wiley & Sons, Inc. Biotechnol Bioeng 63: 730–736, 1999.

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Fructose Caprylate Biosynthesis in a Solvent-free Medium

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Quantitative enzymatic production of 1,6‐diacyl sorbitol esters

Enzymatic synthesis of α‐butylglucoside lactate: A new α‐hydroxy acid derivative

Enzymatic synthesis of unsaturated fatty acid glucoside esters for dermo-cosmetic applications

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