Effect of different reaction parameters on the lipase-catalyzed selective acylation of polyhydroxylated natural compounds in ionic liquids

Katsoura, MH; Polydera, AC; Katapodis, P; Kolisis, FN; Stamatis, H

dc.contributor.author	Katsoura, MH	en
dc.contributor.author	Polydera, AC	en
dc.contributor.author	Katapodis, P	en
dc.contributor.author	Kolisis, FN	en
dc.contributor.author	Stamatis, H	en
dc.date.accessioned	2014-03-01T01:26:11Z
dc.date.available	2014-03-01T01:26:11Z
dc.date.issued	2007	en
dc.identifier.issn	1359-5113	en
dc.identifier.uri	https://dspace.lib.ntua.gr/xmlui/handle/123456789/17963
dc.subject	Biocatalysis	en
dc.subject	Flavonoids	en
dc.subject	Ionic liquids	en
dc.subject	Lipase	en
dc.subject	Phenolic glucosides	en
dc.subject	Response surface methodology	en
dc.subject.classification	Biochemistry & Molecular Biology	en
dc.subject.classification	Biotechnology & Applied Microbiology	en
dc.subject.classification	Engineering, Chemical	en
dc.subject.other	Acylation	en
dc.subject.other	Biocatalysts	en
dc.subject.other	Catalysis	en
dc.subject.other	Ionic liquids	en
dc.subject.other	Parameter estimation	en
dc.subject.other	Reaction kinetics	en
dc.subject.other	Regioselectivity	en
dc.subject.other	Flavonoids	en
dc.subject.other	Lipase	en
dc.subject.other	Phenolic glucosides	en
dc.subject.other	Polyhydroxylated natural compounds	en
dc.subject.other	Response surface methodology	en
dc.subject.other	Enzyme kinetics	en
dc.subject.other	Candida antarctica	en
dc.title	Effect of different reaction parameters on the lipase-catalyzed selective acylation of polyhydroxylated natural compounds in ionic liquids	en
heal.type	journalArticle	en
heal.identifier.primary	10.1016/j.procbio.2007.07.004	en
heal.identifier.secondary	http://dx.doi.org/10.1016/j.procbio.2007.07.004	en
heal.language	English	en
heal.publicationDate	2007	en
heal.abstract	The effect of various reaction parameters on the enzymatic acylation of plant polyhydroxylated compounds, including phenolic and flavonoid glucosides (salicin, helicin, esculin and naringin), was investigated in imidazolium-based ionic liquids (1-butyl-3-methylimidazolium tetrafluoroborate [bmim]BF4 and 1-butyl-3-methylimidazolium hexafluorophosphate [bmim]PF6), using immobilized lipase B from Candida antarctica. The conversion yield, the regioselectivity and the reaction rate of the biocatalytic process strongly depended on the ionic liquid used, their water content, the incubation temperature, as well as the solubility and the concentration of substrates. For most glucosides tested, one major product (monoacylated derivative) was detected as a result of the acylation of the primary hydroxyl group of glucose moiety. The acylation rate and the regioselectivity of the process are higher in [bmim]BF4, where the solubility of all glucosides is significantly higher than in [bmim]PF6 or acetone. Response surface methodology (RSM) based on a five level-three variable central composite circumscribed design, was employed to evaluate the interactive effect of the molar ratio of substrates (MR), the initial concentration of glucoside (N) and the reaction time (RT), as well as for their optimization in [bmim]BF4. At the optimal reaction conditions the maximum acylation yield was 87%. The amount of monoacylated derivatives produced in a single-step biocatalytic process reached values up to 31.6 g/l which is considerably higher than those reported for organic media. (c) 2007 Published by Elsevier Ltd.	en
heal.publisher	ELSEVIER SCI LTD	en
heal.journalName	Process Biochemistry	en
dc.identifier.doi	10.1016/j.procbio.2007.07.004	en
dc.identifier.isi	ISI:000249714700010	en
dc.identifier.volume	42	en
dc.identifier.issue	9	en
dc.identifier.spage	1326	en
dc.identifier.epage	1334	en