Ultrasound-promoted enzymatic synthesis of troxerutin esters in nonaqueous solvents

Ultrasonics Sonochemistry
Yong-mei XiaoXian-fu Lin

Abstract

Comparative studies of enzymatic acylation of troxerutin by the alkaline protease from Bacillus subtilis under ultrasound and shaking were carried out in nonaqueous media. Using divinyl dicarboxylates (CH(2)CH-OOC-(CH(2))(n)-COO-CHCH(2), n=2, 3, 4, 7, 8, 11) featuring different chain length as acyl donors, troxerutin was regioselectively acylated at B ethoxyl group, whether under ultrasound or shaking. Ultrasonic treatment increased the reaction rate and led to high conversion. Several factors, such as pre-irradiation on the enzyme, the power and frequency of the ultrasound, operation manner, as well as the length of the acyl donors were investigated. Using enzyme pre-irradiated for 8 h, the conversion of troxerutin was increased to 87.3% compared with 56.3% obtained from the untreated enzyme. Experimental results also showed that continual ultrasound caused greater rate acceleration than interval ultrasound. Powers of 100, 150 and 200 W, frequencies of 40, 80 and 100 kHz all showed significant improvement on the transesterification, with the greatest effect observed at 150 W, 80 kHz. The acceleration effect increased as the chain length of the acyl donors decreased from C(13) to C(4).

References

Apr 30, 2002·Ultrasound in Medicine & Biology·Valentina SuchkovaCharles W Francis
Jul 26, 2005·Carbohydrate Research·Yong-mei XiaoXian-fu Lin
Oct 27, 2007·Bioprocess and Biosystems Engineering·Zhi-Gang ChenYong-Bin Han
Feb 1, 2008·Chemistry Central Journal·Shweta Shah, Munishwar Nath Gupta
Nov 4, 2008·Journal of Pharmaceutical Sciences·Steliyan TinkovConrad Coester
Dec 5, 2008·Journal of Materials Science. Materials in Medicine·M NichiforC D Radu
Mar 12, 2009·The Journal of Organic Chemistry·Malgorzata MusialikGrzegorz Litwinienko

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Citations

Apr 12, 2011·Journal of the Science of Food and Agriculture·Jing WangBaoguo Sun
Sep 8, 2015·Analytica Chimica Acta·M M Delgado-Povedano, M D Luque de Castro
Jul 5, 2011·Biotechnology Advances·Barbara KwiatkowskaDavid H Bremner
Jun 10, 2016·Applied Microbiology and Biotechnology·Io AntonopoulouVincenza Faraco
Oct 6, 2016·Topics in Current Chemistry·Micheline Draye, Nathalie Kardos
Aug 9, 2013·Biotechnology Progress·Ahmad Ziad SulaimanYusuf Chisti
Dec 21, 2013·ChemSusChem·Manoj B GawandeRajender S Varma

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