Lipase-catalyzed regioselective acylation of sucrose in two-solvent mixtures

• Published in: Biotechnology and bioengineering Vol. 65; no. 1; pp. 10 - 16
• Main Authors: Ferrer, M, Cruces, M.A, Bernabe, M, Ballesteros, A, Plou, F.J
• Format: Journal Article
• Language: English
• Published: New York John Wiley & Sons, Inc 05-10-1999; Wiley
• Subjects: 6-O-^Alauroylsucrose; 6-O-^Apalmitoylsucrose; Acylation; Binding Sites; Bioconversion; Bioconversions. Hemisynthesis; Biological and medical sciences; Biosynthesis; Biotechnology; biotransformation; biotransformations; Butanols; Catalysis; Catalyst selectivity; Dimethyl Sulfoxide; Enzyme kinetics; Esterification; Fundamental and applied biological sciences. Psychology; In Vitro Techniques; Lipase - metabolism; lipases; Magnetic Resonance Spectroscopy; Methods. Procedures. Technologies; Microorganisms; Mitosporic Fungi - enzymology; Mixtures; Pentanols; regioselectivity; Solvents; sucrose; Sucrose - analogs & derivatives; Sucrose - chemistry; Sucrose - metabolism; sucrose esters; Sugar (sucrose); triacylglycerol lipase; vinyl esters; Enzymatic synthesis; Regioselectivity; Sucrose; Enzyme; Triacylglycerol lipase; Enzymatic catalysis; Esterases; Transesterification; Optimization; Carboxylic ester hydrolases; Ester; Organic solvent; Hydrolases; Acylation
• ISSN: 0006-3592; 1097-0290
• DOI: 10.1002/(SICI)1097-0290(19991005)65:1<10::AID-BIT2>3.0.CO;2-L

The enzymatic synthesis of 6-O-lauroylsucrose and 6-O-palmitoylsucrose was performed by transesterification of sucrose with the corresponding vinyl esters in a medium constituted by two solvents. More specifically, the acylation was carried out in 2-methyl-2-butanol (tertamyl alcohol) containing a low percentage (not higher than 20%) of dimethyl sulfoxide. Several lipases were able to catalyze the transesterification, but that from Humicola lanuginosa (adsorbed on diatomaceous earth) was particularly useful. We optimized the synthesis of 6-O-lauroylsucrose varying the percentage and nature of the cosolvent, the molar ratio sucrose/vinyl laurate, the nature of bulk solvent and the enzyme content. Under the best conditions, (2-methyl-2-butanol/DMSO 4:1 v/v), a sucrose conversion of 70% to 6-O-lauroylsucrose was achieved in 24 h using 50 mg biocatalyst/mL. As a side process, a low percentage (< 5% in 24 h) of the initial sucrose is converted into the diesters 6,1'-di-O-lauroylsucrose and 6,6'-di-O-lauroylsucrose. The above methodology was also extended to the synthesis of 6-O-palmitoylsucrose. The acylation process was even faster, giving rise to an 80% conversion to monoester in 48 h using 25 mg biocatalyst/mL. This study shows that the use of two-solvent mixtures may become a feasible alternative for the synthesis of sucrose esters, allowing to exploit the catalytic potential of lipases.