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Enzymatic synthesis of unsaturated fatty acid glucoside esters for dermo‐cosmetic applications
Author(s) -
Bousquet MariePierre,
Willemot RenéMarc,
Monsan Pierre,
Boures Emmanuel
Publication year - 1999
Publication title -
biotechnology and bioengineering
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.136
H-Index - 189
eISSN - 1097-0290
pISSN - 0006-3592
DOI - 10.1002/(sici)1097-0290(19990620)63:6<730::aid-bit11>3.0.co;2-j
Subject(s) - enzyme , chemistry , glucoside , fatty acid , biochemistry , organic chemistry , medicine , alternative medicine , pathology
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.