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

Abstract

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.

Expression and Characterization of a Novel Thermo-Alkalistable Lipase from Hyperthermophilic Bacterium Thermotoga maritima

“…Enzyme catalysis in organic solvents needs the right amount of water, which directly affects the activity of enzyme. If the amount of water is too large in the reaction system, the catalytic behavior should be changed, which leads to the change of the reaction balance, even losing the catalytic activity [35,36]. It may be speculated that the moisture content was higher than the optimal water amount in reaction system; the flexibility of the enzyme structure became too large, leading to the change of enzyme conformation and deactivation.…”

Synthesis of Surfactants Using Enzymes

“…The alkylation step is most favourable with short alcohols (see below), with butanol as a good example [29]. Enzymatic esterification of butyl glucoside with unsaturated fatty acids has generated products of interest for dermo-cosmetic applications [30].…”

Lipophilisation de composés phénoliques par voie enzymatique et propriétés antioxydantes des molécules lipophilisées

“…La plus commune de ces modifications consiste en une alkylation préalable du composé hydrophile, entraînant la formation d'un pont éther. Les dérivés méthyliques, éthyliques, propyliques ou butylalkyliques de glucides sont également intéressants pour certaines réactions de lipophilisation biocatalysée, malgré le fait que cette stratégie nécessite une étape supplémentaire de déprotonation à la fin du procédé [23][24][25]. Les groupes protecteurs de type isopropylidène, benzylidène ou cyclohexylidène sont aussi fréquemment employés pour l'hydrophobation, ce qui améliore la solubilité du substrat dans les solvants sélectionnés.…”